Podcasts by Why Won

Why Won

Dating can be a hot mess, from being ghosted by your crush to realizing that you

Further podcasts by Headgum

Podcast on the topic Beziehungen

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Why Won
Married in a Hospital (w/ Danielle Pinnock) from 2023-11-30T12:37:10.293653

Danielle Pinnock (Young Sheldon, Ghosts) and Nicole get mistaken for each other... a lot.  The comedian and writer chats with Ni...

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Why Won
The System is Broken (w/ Lilly Singh) from 2023-11-30T12:37:10.277332

Comedian, actress and YouTuber star Lilly Singh (A Little Late with Lilly Singh, Dollface) chats with Nicole about April Fools' Day pr...

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Why Won
How to have a WAP (w/ Donnell Rawlings) from 2023-11-30T12:37:10.273464

Comedian Donnell Rawlings (Chappelle's Show, Winning Time: The Rise of the Lakers Dynasty) chats with Nicole about the powers of having a WA...

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Why Won
Married, but Living Apart (w/ Judy Gold) from 2023-11-30T12:37:10.257804

The hilarious Judy Gold joins Nicole to chat about the challenges of dating a therapist, her experience being selected as one of Time Out New York's Most E...

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Why Won
Farting in Bed with your Lover (w/ Sudi Green) from 2023-11-30T12:37:10.248952

Comedian and writer Sudi Green (SNL, I Love That For You) joins Nicole to discuss their awkward encounters with celebrities, havin...

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Why Won
Caught Cheating... Twice! (w/ Ketra Long) from 2023-11-30T12:37:10.240144

Comedian Ketra Long joins Nicole to tell the story about how she got caught cheating twice in her relationship. She also shares the time she con...

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Why Won
Bringing Down Your Walls (w/ Penn Badgley) from 2023-11-30T12:37:10.238302

Oh my god, he's here. Penn Badgley (You, Gossip Girl, host of Podcrushed) joins Nicole to ...

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Why Won
Hired a Matchmaker (w/ Amy Aniobi) from 2023-11-30T12:37:10.216508

Writer/director Amy Aniobi (Silicon Valley, 2 Dope Queens) joins Nicole to discuss her experience dating with the help of a profes...

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Why Won
Relationship Baggage (w/ Justin Cunningham) from 2023-11-30T12:37:10.206532

Actor and co-star Justin Cunningham (Grand Crew) chats with Nicole about recognizing toxic relationships, finding a pa...

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Why Won
A Halloween Wedding (w/ Mary Holland) from 2023-11-30T12:37:10.203435

Friend and comedian  Mary Holland (Corked podcast) chats with Nicole about having a...

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Why Won
Praise Kink (w/ Jujubee) from 2023-11-30T12:37:10.191164

Iconic drag queen Jujubee (Drag Race S2, All-Stars 1 and 5) joins Nicole to reminisces over her many seasons of drag competiti...

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Why Won
Set Up (w/ Aimee Carrero) from 2023-11-30T12:37:10.175690

Actress Aimee Carrero (She-Ra, Elena of Avalor) joins Nicole to discuss hookup hygiene standards, marrying the man she was set ...

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Why Won
How to Hack Into Your Partner's Phone (w/ Keke Palmer) from 2023-11-30T12:37:10.155968

Emmy-award winning actress Keke Palmer (Nope, Lightyear) shares with Nicole how she got her first kiss from MySpace, why she avoids posting re...

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Why Won
The First Black Chippendale Dancer (w/ Quentin Plair) from 2023-11-30T12:37:10.146748

Actor Quentin Plair (Welcome to Chippendales) chats with Nicole about the fetishization faced with being the first Black Chip...

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Why Won
Stories from Nicole's Road Dog (w/ Christi Chiello) from 2023-11-30T12:37:10.133014

Comedian and Nicole's opener Christi Chiello joins the podcast to discuss having 5 of her ex-boyfriends come out as gay, why theatre...

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Why Won
Celibate for 18 Years (w/ Debra DiGiovanni) from 2023-11-30T12:37:10.117809

Comedian Debra DiGiovanni joins Nicole to discuss her experience being single and celibate for 18 years, importing her curr...

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Why Won
Marrying Your High School Sweetheart (w/ Adam Pally) from 2023-11-30T12:37:10.105086

Comedian Adam Pally (101 Places to Party Before You Die, Who Invited Charlie?) chats with Nicole about why an easy relationship i...

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Why Won
A Love Queen (w/ Sasha Velour) from 2023-11-30T12:37:10.087433

Drag queen icon Sasha Velour (winner of Drag Race S9) chats with Nicole about coming out to their dad at a TGI Fridays, the chal...

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Why Won
Secrets To a Long, Loving Marriage (w/ John Leguizamo) from 2023-11-30T12:37:10.073771

Actor John Leguizamo (Encanto, Moulin Rouge!, Ice Age) chats with Nicole about his secrets to a long, loving marriage, how he ...

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Why Won
Live Your Rom-Com Era (w/ Sam Taggart) from 2023-11-30T12:37:10.054504

Comedian Sam Taggart (host of StraightioLab) is h...

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Why Won
Transcending Norms (w/ TS Madison) from 2023-11-30T12:37:10.051541

Actress and activist TS Madison (judge on RuPaul's Drag Race) is here for a heartfelt chat on her journey from being a viral TikTok sens...

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Why Won
Nicole Wins an Orgasm Contest (w/ Matteo Lane) from 2023-11-30T12:37:10.039476

Comedian and friend Matteo Lane returns to the podcast! They reminisce about his love life since his last episode, getting kicked off Gr...

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Why Won
Gay Orgies (w/ Jay Jurden) from 2023-11-30T12:37:10.025280

The hilarious comedian Jay Jurden joins Nicole to talk about his secret relationship with a frat boy, working at Abercrombie & Fitch duri...

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Why Won
Feeling Safe in a Relationship (w/ Uzo Aduba) from 2023-11-30T12:37:10.010119

The Emmy-winning Uzo Aduba (Orange Is The New Black) chats with Nicole about how her dating app DMs changed after booking Crazy Eyes, find...

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Why Won
Sex and Love Addict (w/ Maria Bamford) from 2023-11-30T12:37:10.006900

Ever wondered what it's like getting intimate with a clown? Deep dive as comedian Maria Bamford (Arrested Development, Big Mouth...

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Why Won
Advice From an Intimacy Expert (w/ Shan Boodram) from 2023-11-30T12:37:09.995942

Sexologist and intimacy expert Shan Boodram (Sexology, Lovers & Frie...

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Why Won
Saying I Love You (w/ Ashley Blaine Featherson-Jenkins) from 2023-11-30T12:37:09.980569

Actress Ashley Blaine Featherson-Jenkins (Dear White People, Grand Crew) joins Nicole to chat about her perfect engagement stor...

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Why Won
The Celibacy Choice (w/ Kel Mitchell) from 2023-11-24T17:51:29

Comedian Kel Mitchell (Kenan & Kel, Good Burger) joins Nicole to explore his evolution from teen heartthrob to youth pastor. ...

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Why Won
How to Spot a Hobosexual (w/ Alesha Reneé) from 2023-11-17T09:30

Actress & TV personality Alesha Reneé (Grand Crew, Girl Code) joins Nicole to delve into the world of 'hobosexuals,' revealing her e...

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Why Won
Reading Nicole's Fortune (w/ Witch Sutton Crawford) from 2023-11-10T09:00

Ever wonder what it's like to have your tarot cards read? Witch and intuitionist Sutton Crawford gives Nicole an on-air reading rega...

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Why Won
Kink Gone Wrong (w/ Jonathan Van Ness) from 2023-10-27T08:00

Hairstylist and icon Jonathan Van Ness (Queer Eye) shares with Nicole an unforgettable and horrifying story about his first foray into the kin...

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Why Won
Relationship Manipulation Tactics (w/ E.R. Fightmaster) from 2023-10-20T09:00

Comedian E.R. Fightmaster (Shrill, Grey's Anatomy) joins Nicole to discuss the benefits of keeping romantic partnerships o...

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Why Won
Hurt People Hurt People (w/ Kenny DeForest) from 2023-10-13T08:30

Comedian Kenny DeForest joins Nicole to explore how an amicable split after 8.5 years can transform someone from a 'fuckboy' to a 'bo...

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Why Won
Breaking Up (w/ Eric Andre) from 2023-09-29T08:00

Is it worse to break up with someone, or get broken up with? Comedian Eric Andre (Listen

Why Won
Positive Affirmations to Change Your Psyche (w/ Leslie Jones) from 2023-09-22T08:00

Comedian Leslie Jones (SNL) chats with Nicole about the challenges of adjusting to a new relationship, strategies to eliminate negative s...

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Why Won
Achieving'Couple Goals'(w/ Michael Jai White) from 2023-09-15T08:00

Ever wondered what lies behind those picture-perfect 'couple goals'? Action star Michael Jai White (Black Dynamite, Outlaw Jo...

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Why Won
Nicole Eats a Banana from a Sex Worker's Pussy (w/ Naomi Rodgers) from 2023-08-25T09:00

Broadway star Naomi Rodgers (Tina: The Tina Turner Musical) opens up about secretly dating her co-star while on tour, and offe...

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Why Won
Romancing Overseas (w/ Zurin Villanueva) from 2023-08-11T08:00

Broadway superstar Zurin Villanueva (Tina: The Tina Turner Musical)  joins Nicole for a discussion about the awkwardness of working to...

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Why Won
Dating an Asexual (w/ Gigi Goode) from 2023-07-28T08:00

Drag queen Gigi Goode (Drag Race S12) joins Nicole for a supersized live episode of the podcast! They talk about her trans jour...

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Why Won
Catfishing Men on Craigslist (w/ Bosco) from 2023-07-14T08:00

Drag queen Bosco (Drag Race S14) joins Nicole to discuss their long-term relationship with a fan, recounts her most enchanting f...

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Why Won
Tasteful Dick Pics (w/ Jermaine Fowler) from 2023-06-30T08:00

Comedian & actor Jermaine Fowler (The Blackening) joins Nicole to reminisce on their time working on Guy/Girl Code, his joy of being...

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Why Won
Finding Your Confidence (w/ Jay Pharoah) from 2023-06-23T09:28:12

Comedian Jay Pharoah (Saturday Night Live) dives into how a messy breakup ended up saving his SNL career, and the bizarre role Do...

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Why Won
Fake It Til You Make It (w/ Melvin Gregg) from 2023-06-16T08:00

Comedian and actor Melvin Gregg (Vine, American Vandal, The Blackening) opens up about his unique romantic path, where pr...

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Why Won
Sugar Daddies (w/ Sugar&Spice) from 2023-05-26T08:00

Twin drag queen icons Sugar & Spice (RuPaul's Drag Race S15) join Nic...

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Why Won
Hot Porn Seaches (w/ Bridget Everett) from 2023-05-19T08:00

The hilarious Bridget Everett (Somebody, Somewhere) joins Nicole to discuss the hot porn searches they've been into, the need...

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Why Won
Lesbian Sex (w/ Ashley Gavin) from 2023-04-28T08:00

Comedian Ashley Gavin (host of We're Having Gay Sex) teaches Nicole all about lesbian se...

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Why Won
Staying Friends with your Ex (w/ James Marsden) from 2023-04-14T12:47:13

Actor James Marsden (Sonic The Hedgehog, Hairspray, Jury ...

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Why Won
Why Won't You Go Get a Transvaginal Ultrasound? (w/ X Mayo) from 2023-03-31T08:00

Comedian and writer X Mayo (The Daily Show, American Auto, Swarm) chats with Nicole about her success making friend co...

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Why Won
Marrying for Tax Purposes (w/ Jeff Hiller) from 2023-03-24T08:00

Comedian and actor Jeff Hiller (Somebody Somewhere) reunites with Nicole to share how he met his husband on C...

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Why Won
Being'In Like'vs Being'In Love'(w/ Gabrielle Dennis) from 2023-03-17T08:00

Comedian and actress Gabrielle Dennis (A Black Lady Sketch Show, Luke Cage) chats with Nicole her philosophy as to why fall...

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Why Won
Mormon and Closeted (w/ Bridger Winegar) from 2023-03-10T10:00

Writer Bridger Winegar (host of I Said No Gifts!)  joins Nicole to discuss his ...

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Why Won
Being The Only One Left (w/ Michael Cruz Kayne) from 2023-02-24T09:00

Comedian Michael Cruz Kayne's dating strategy involves being the only guy left available. He joins Nicole to explain the approach and the success that...

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Why Won
Dating a Groupie (w/ Steph Tolev) from 2023-02-17T09:00

Comedian Steph Tolev joins Nicole to discuss what it's like to date a groupie, getting matching tattoos with her partners, her experienc...

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Why Won
Having Sex On-Camera (w/ Jordan Firstman) from 2023-02-10T09:00

Comedian Jordan Firstman (Big Mouth, Ms. Marvel) joins Nicole to talk about his experience being involved in a threesome where ev...

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Why Won
Nicole's Boyfriend Speaks His Truth (w/ Dan Black) from 2023-01-27T09:00

In January, Nicole shocked the world with an Instagram post announcing her relationship with comedian Listen

Why Won
The Sex Lives of Artists (w/ Ilia Isorelýs Paulino) from 2023-01-20T09:00

Actress Ilia Isorelýs Paulino (The Sex Lives of College Girls)  joins Nicole to chat about her sex life at Yale, being 6′2, gro...

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Why Won
Pandemic Divorce (w/ Punkie Johnson) from 2023-01-13T09:00

Comedian Punkie Johnson (SNL) joins Nicole to discuss how the pandemic lead to her divorce,  learning to love her partner's ug...

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Why Won
Living Your Hoe Phase (w/ Atsuko Okatsuka) from 2022-12-30T09:00

Comedian Atsuko Okatsuka returns! She chats with Nicole about dating her community college teacher for 7 years, exploring the world of...

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Why Won
Eloping on Christmas (w/ Manila Luzon) from 2022-12-23T09:00

Drag queen legend Manila Luzon (Drag Race S3, All-Stars 1 & 4, Drag Den) joins Nicole to discuss her Christmas Eve eloping in La...

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Why Won
Let's Talk About The Bag Dress (w/ LaLa Ri) from 2022-12-16T09:00

On Drag Race, Nicole guest judged one of the most iconic outfits in franchise history - Listen

Why Won
Building Your Date's File (w/ Larry Owens) from 2022-11-25T09:00

Multi-award winning actor and comedian Larry Owens (A Strange Loop, Abbott Elementary) chats with Nicole about his experience attend...

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Why Won
Open Relationships (w/ Cole Escola) from 2022-11-18T09:00

Comedian Cole Escola (Difficult People, Tuca & Bertie) helps Nicole craft the perfect answer for dating app small talk, shares the secre...

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Why Won
Nicole's Kicked off Hinge (w/ Julie Klausner) from 2022-11-11T09:00

Comedian Julie Klausner (Billy on the Street, Difficult People) chats with Nicole about the corny messages she gotten from dating apps, why...

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Why Won
Self-Sabotaging your Relationships (w/ Caleb Hearon) from 2022-10-28T08:00

Comedian Caleb Hearon (Human Resources) joins Nicole to discuss self-sabotaging relationships, dating while still in the closet, and an a...

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Why Won
Playing an Extra in a Porno (w/ Rose Dommu) from 2022-10-21T08:00

Writer Rose Dommu (Out Magazine, Like a Virgin podcast) joins Nicole to chat about the story behind her transitio...

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Why Won
Rewriting the Tinder Bio (w/ John Stamos) from 2022-10-14T08:00

Actor and heartthrob John Stamos (Full House, You, Big Shot) is here to figure out the core of Nicole's dating issues. Stamos tel...

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Why Won
Sex Contracts (w/ Guy Branum) from 2022-09-30T08:00

Comedian Guy Branum (Billy On The Street, Bros) chats with Nicole about establishing sex contracts before a hookup, being a dom/su...

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Why Won
Chased by the KKK (w/ Brandon Kyle Goodman) from 2022-09-23T08:00

Actor and writer Brandon Kyle Goodman (Netflix's Big Mouth, Human Resources) chats with Nicole about the time he was chas...

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Why Won
Comedy Dominatrix (w/ Nori Reed) from 2022-09-16T04:00

Comedian and writer Nori Reed (Raven's Home) chats with Nicole about getting her breast augmentation, how she soft-launched her tra...

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Why Won
The Art of Online Stalking (w/ Sona Movsesian) from 2022-08-26T08:00

Conan's assistant, Sona Movsesian (author: The World’s Worst Assistant) is here! Sona shares how she met her husband at Comic-C...

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Why Won
Throupled (w/ Mae Martin) from 2022-08-19T08:00

Comedian Mae Martin (Feel Good) chats with Nicole about being in a throuple relationship, their experience addicted to drugs, and startin...

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Why Won
Dealing with FBoys (w/ Nikki Glaser) from 2022-08-12T08:00

Comedian Nikki Glaser (FBoy Island, Good Clean Filth) chats with Nicole about being in a 9 year on-and-off again relationship, h...

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Why Won
Main Character Energy (w/ Willow Pill) from 2022-07-22T08:00

Reigning drag queen Willow Pill (winner of RuPaul's Drag Race S14) is here! She chats with Nicole abo...

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Why Won
The Story of a Kissless Virgin (w/ Benton Ray) from 2022-07-15T08:00

Comedian Benton Ray is a kissless virgin. He chats with Nicole about the circumstances of this choice, they learn new terms for different sexual...

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Why Won
A Stalking Ex-Boyfriend, a Gang Member, and a Gun (w/ Aaron Jennings) from 2022-06-24T08:00

Co-star Aaron Jennings (Grand Crew) and Nicole discuss grade school romances, talking finances with your partner, the benefits ...

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Why Won
Having a Drama-Free Divorce (w/ Grasie Mercedes) from 2022-06-17T08:00

Co-star Grasie Mercedes (Grand Crew, Access Hollywood) reflects on her 14-year relationship and the breakthrough she had in therapy ...

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Why Won
Setting Yourself on Fire (w/ Vanity Jay) from 2022-06-10T08:00

Stripper and exotic entertainer Vanity Jay chats with Nicole about all things stripping and sex work. She shares the complicated nature of...

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Why Won
Quit your Job (w/ Kornbread"The Snack"Jeté) from 2022-05-27T08:00

Drag queen and reigning Miss Congeniality Kornbread "The Snack" Jeté (RuPaul's Drag Race S14) joins Nicole for a live episode, wh...

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Why Won
Keeping Relationships Off Social Media (w/ Raja Gemini) from 2022-05-20T08:00

Drag queen icon Raja Gemini (winner of Drag Race S3) joins Nicole to discuss the stress of competing in the first all-winners se...

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Why Won
Coping With Anxiety (w/ Taylor Tomlinson) from 2022-05-13T08:00

Comedian Taylor Tomlinson chats with Nicole about using Instagram to document her panic attacks, coping with anxiety, and the time ...

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Why Won
Do Men Not Like Funny Women? (w/ Drew Lynch) from 2022-04-29T08:00

Comedian and friend Drew Lynch (America's Got Talent S10) chats with Nicole about a harrowing bee incident they had together on tour, ...

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Why Won
Left for my Best Friend (w/ Tika Sumpter) from 2022-04-22T08:00

Actress Tika Sumpter (Sonic The Hedgehog 1 & 2) recounts the times that boys have left her for her best friend, losing her expen...

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Why Won
Bisexual Erasure (w/ Stephanie Beatriz) from 2022-04-15T08:00

Actress Stephanie Beatriz (Encanto, Brooklyn Nine-Nine) chats with Nicole about leaving a 9 year relationship, dealing with...

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Why Won
Nicole gets a special delivery of hot gossip from 2022-03-31T04:30

If there’s anyone who loves mindless gossip more than Nicole, it’s her good pal Solomon Georgio. In fact, it’s the subject of his brand new podcast from Team Coco, Listen

Why Won
Mistaken Identity (w/ Raven Goodwin) from 2022-03-25T08:00

Actress Raven Goodwin (Single Black Female, SMILF) shares her worst first dates, the adorable story behind her picnic proposal,...

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Why Won
Twin Divorce (w/ Darcey and Stacey Silva) from 2022-03-18T08:00

Oh my god, it’s happening. Twins Darcey and Stacy Silva (TLC's 90 Day Fiancé: Before the 90 Days, Darcey & Stacey) are here! T...

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Why Won
Granny Chaser (w/ Tenderoni) from 2022-03-11T09:00

Drag king Tenderoni (Winner of The Drag Queen of the Year Pageant 2021) chats with Nicole about why they love older women, the challeng...

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Why Won
Sensitive Boys (w/ Jackie Fabulous) from 2022-02-25T09:00

Comedian and motivational speaker Jackie Fabulous joins Nicole to chat about negotiating prenups, how to gently give direction durin...

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Why Won
Tinder Troubles (w/ Will Hines) from 2022-02-22T00:21:35.552108

On the first episode of Why Won't You Date Me, Will Hines (UCB Comedy, Don't Get Me Started, CollegeHumor) joins Nicole to rate her Tinder game, discuss her past green card marriage, and talk about...

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Why Won
Bad Hookups (w/ Dan Lippert) from 2022-02-22T00:21:35.550800

Dan Lippert (UCB Comedy, Comedy Bang Bang) joins us to talk about Nicole's abandonment issues, the time she blew him in a bathroom, and Nicole shares the time she slept with a guy with a literal BR...

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Why Won
We're Getting Juiced (w/ Alison Rich) from 2022-02-22T00:21:35.547337

Alison Rich (The Goldbergs, Party Over Here) joins Nicole for a nice juicing. Get ready to listen to some crazy Tinder hookup stories, find out how Nicole is connected to the Kardashians, and the t...

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Why Won
Bad Threesomes (w/ Matteo Lane) from 2022-02-22T00:21:35.543475

Nicole's good friend Matteo Lane (Guy Code, @midnight, Ladylike) is on the podcast to rate Nicole's Tinder, talk about their experiences with threesomes, and discuss the horrors of sucking a dirty ...

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Why Won
Featuring the Man Who's Floor I Peed On (w/ EJ Wolborsky) from 2022-02-22T00:21:35.542229

EJ isn't a comedian, but just a nice guy who's floor Nicole peed on after a drunken party at an Apple store. Hear them reconcile on what happened that fateful night, and for some wholesome dating a...

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Why Won
Dating Fans (w/ Mike Mitchell) from 2022-02-22T00:21:35.539586

This week Mike Mitchell (The Birthday Boys, Doughboys, Love) is on the show to get his Tinder profile rated, discuss whether they would date fans, and why he doesn't like sharing a bed in a relatio...

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Why Won
The 5 Love Languages (w/ Warren Burke) from 2022-02-22T00:21:35.538166

Warren Burke (Jimmy Kimmel Live!) talks Nicole through her intimacy issues, the 5 love languages, and the time she got mistaken for a hooker.

You can play along and see Nicole's Tinder bio...

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Why Won
Nicole's finally on Raya! (w/ Eliza Skinner) from 2022-02-22T00:21:35.492847

With the help from Eliza Skinner (The Late Late with James Corden, Drop The Mic) Nicole is finally on Raya! They discuss what the exclusive dating platform is like, and if they would ever date thei...

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Why Won
Advice from a Married Couple (w/ Madeline Walter and Ben Greene) from 2022-02-22T00:21:35.489042

It's Why Won't You Date Me's first married couple guest! Madeline Walter (UCB, Definitely Dying podcast) and Ben Greene (UCB, On The Cusp podcast) discuss the crazy drunken story that nearly made t...

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Why Won
Nicole's Figuring Out Her Sexuality (w/ Zainab Johnson) from 2022-02-22T00:21:35.484729

Zainab Johnson (Stand-up, HonesTEA with Z podcast) is here to answer all of Nicole's questions on the Muslim religion, what being "emotionally unavailable" means, and Nicole think she's finally fig...

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Why Won
Take a Look at Nicole's new Tinder Bio! (w/ Zeke Nicholson) from 2022-02-22T00:21:35.483689

Zeke Nicholson (A.P. Bio, Take My Wife, Lopez) joins Nicole to share stories from their first acting gigs, discuss the incestuous feel of dating people in the comedy community, and Zeke rates Nicol...

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Why Won
Racism in Hollywood (w/ Oscar Montoya) from 2022-02-22T00:21:35.479570

Oscar Montoya (UCB, Inside the Disney Vault podcast) joins Nicole to talk through his 4 year dry spell, Mario Betalli's mitten hands, and the rampant racism in Los Angeles.

You can play al...

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Why Won
Boyfriendless Forever (w/ Marcella Arguello) from 2022-02-22T00:21:35.475865

Marcella Arguello (stand up, @midnight) joins Nicole to share their love for sucking dick, her worry for being fetishized as a tall woman, and gives Nicole great advice for her Tinder profile.
...

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Why Won
Booty Call Horror Story (w/ Jameela Jamil) from 2022-02-22T00:21:35.470767

Jameela Jamil (The Good Place) chats about how she got cast in The Good Place, the rejection she got as a child, and shares her most horrifying Tinder date.

Check out Jameela's "I Weigh" I...

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Why Won
Nicole's Horny (w/ Mary Sasson) from 2022-02-22T00:21:35.466859

Mary Sasson (UCB) discusses the ever growing trends in women's bodies. Nicole talks about the worst dicks she's slept with and makes an apology to her Pizza match on Tinder. Also, Nicole's like rea...

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Why Won
Vagina Talk (w/ Megan Neuringer) from 2022-02-22T00:21:35.462852

"With size, there's truly no winning in being an objectified woman."

Megan Neuringer (writer, Portlandia) talks about body anxieties at every size, teaches Nicole about her ovaries and how...

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Why Won
Is It OK to Google Your Dates? (w/ Kara Klenk) from 2022-02-22T00:21:35.461775

"He gave the podcast people more insight into why we broke up than he did to me"

Turns out, talking about your relationship publicly on podcasts could be troublesome. Kara Klenk (Magic for...

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Why Won
Love, Lust, and Infatuation (w/ Baron Vaughn) from 2022-02-22T00:21:35.458098

"Everyone is doing monogamy. And if you try to cram all those people into one door, someone is gonna get hurt."

Baron Vaughn (Corporate, The New Negros) explains LOVE. What it is to be a l...

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Why Won
Finding your S/O's Pet Name (w/ Elizabeth Ho) from 2022-02-22T00:21:35.454309

Did you know that couples with pet names statistically have longer lasting relationships? In today's episode, Nicole and Elizabeth Ho (Disjointed) consider what pet name they would want to have. El...

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Why Won
Dealing with Creeps (w/ Trixie Mattel) from 2022-02-22T00:21:35.450025

Trixie Mattel (Winner of RuPaul's Drag Race: All Stars Season 3) discusses getting touched by strangers in public, being in an "It's Complicated" relationship on Facebook, shares getting catfish'd ...

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Why Won
Period Horror Stories (w/ Toni Charline) from 2022-02-22T00:21:35.449084

Periods suck. Toni Charline (UCB) joins Nicole to share all their embarrassing period-related stories. From their first tampon applications, to getting a period mid-Doughboys recording, and the tim...

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Why Won
How to Kiss (w/ Matt Ingebretson) from 2022-02-22T00:21:35.446092

"A fun thing that I like to do is when kissing someone, is to open my eyes to see what their face looks like."

Matt Ingebretson (Corporate) talks all about kissing - the stress of going in...

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Why Won
Putting Faith in your Love Life (w/ Liza Treyger) from 2022-02-22T00:21:35.445244

"Go out into the world with confidence, not desperation."

Can crystals and candles help with your love life? Liza Treyger (stand-up, Horace and Pete) joins Nicole to discuss their benefits...

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Why Won
BONUS: Bad Birthday Hookup (LIVE w/ Dulcé Sloan) from 2022-02-22T00:21:35.441453

"If he had chest hair, I would've had rug burn. That's all I'm saying."

Dulcé Sloan (The Daily Show with Trevor Noah) discuss their mutual hate for Coffee Meets Bagel, share some of their ...

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Why Won
Death & Taxes (w/ Punam Patel) from 2022-02-22T00:21:35.440583

"Would I rather live a shorter life where I'm happier, than a long one where I have to work so hard to be healthy? More often than not I choose shorter."

Things get serious in this episode...

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Why Won
Heckled Online and Offline (w/ Miel Bredouw) from 2022-02-22T00:21:35.402458

"I hope my dad ate ass."

Miel Bredouw (Punch Up The Jampodcast) joins Nicole to discuss online harassment, what it was like to 'date' on Vine and what kind of sex their parents would've be...

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Why Won
BONUS: The One That Got Away (w/ Blair Socci) from 2022-02-22T00:21:35.397685

Blair Socci (stand-up, The Blair & Greta Show) discusses what it's like to date an "influencer", how to have an amicable break up with your ex, and the pro/cons of dating comedians. Plus, Nicole re...

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Why Won
Sleeping with DJs (w/ Greta Titelman) from 2022-02-22T00:21:35.396754

"What happens in Vegas, stays in Vegas... But not this."

Greta Titelman (The Worst podcast) breaks the double-standard behind having sex on a first date, talks about their first masturbati...

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Why Won
Nicole's Choice of Porn (w/ Ronnie Adrian) from 2022-02-22T00:21:35.370489

"I'm crazier than you. I'll fuck you up with these dildos"

Ronnie Adrian (Comedy Bang Bang, White Women) joins Nicole to discuss their mutual struggle with flirting, and the best way to en...

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Why Won
Power-Bottom (w/ Monique Heart) from 2022-02-22T00:21:35.366468

"I thought I had contracted an STD where I was rotting from the inside"

Drag queen Monique Heart (RuPaul's Drag Race Season 10, All Stars Season 4) has never been in a real relationship. H...

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Why Won
The Joy of Being Alone (w/ Ashley Nicole Black) from 2022-02-22T00:21:35.365585

"I would love for Guy Fieri to narrate my sex"

Ashley Nicole Black (Full Frontal with Samantha Bee, A Black Lady Sketch Show) joins Nicole to share her love of being alone, whether they li...

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Why Won
Dating Someone with Commitment Issues (w/ Fortune Feimster) from 2022-02-22T00:21:35.361699

"You only get to cuddle if there's been penetration."

Fortune Feimster (The Mindy Project, Chelsea Lately) shares the cute story how she met her fiancee at Pride, how coming out late in li...

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Why Won
Crying Boys (w/ Laci Mosley) from 2022-02-22T00:21:35.357742

"All I want is a dick that is also a coat rack."

Laci Mosley (Florida Girls, Scam Goddess podcast) discusses reckless driving, which dating app has the cutest guys, and how she injured her...

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Why Won
Why Everybody Needs Therapy (w/ Therapist John Kim) from 2022-02-22T00:21:35.352754

Licensed therapist John Kim (aka The Angry Therapist, author of I Used to Be a Miserable F*ck) discusses the stigma stopping many PoC to join therapy, the challenges of being vulnerable as a therap...

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Why Won
Living with Nicole Byer (w/ John Milhiser) from 2022-02-22T00:21:35.348816

Nicole's roommate John Milhiser (SNL, CollegeHumor) discuss how Nicole serves as a third in his relationship, if they've ever heard each other have sex, and their dog's drug problem. Plus, he share...

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Why Won
Running into Past Flings (Live w/ Josh Sharp) from 2022-02-22T00:21:35.345028

Josh Sharp (The Opposition with Jordan Klepper, The Chris Gethard Show) joins Nicole to discuss their previous liveshow where Nicole ran into a guy who she's slept with. They also discuss Josh's op...

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Why Won
Drugs & Dogs (w/ Eric Edelstein) from 2022-02-22T00:21:35.340374

'She saved me in her phone as 'Eric Weirdo".

Eric Edelstein (Jurassic World, American Dad) shares the story behind meeting Jess, his lovely dog grooming wife. Him and Nicole also discusses...

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Why Won
BONUS: The Struggles of your Twenties (w/ Rae Sanni) from 2022-02-22T00:21:35.201957

Writer/stand-up Rae Sanni (The Good Place, A Black Lady Sketch Show) joins Nicole to discuss all the struggles of their twenties, and how it has defined them. From the string of bad sex, hustling f...

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Why Won
Open Relationships (w/ Kelly Hudson) from 2022-02-22T00:21:35.201120

"My life's work was dating people."

Kelly Hudson (Search Party, Sunnyside, CollegeHumor) left her open-relationship to be with the man she's married to today. She shares her tricky experie...

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Why Won
Loving Your Boobs (w/ Amy Miller) from 2022-02-22T00:21:35.197544

Stand-up comedian & Nicole's opener Amy Miller (host of Who's Your God) teaches us how to spot a chucklefucker, shares her experience going through Steve Harvey's 90 day sex rule, and how to feel p...

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Why Won
Quarantine Breakup (w/ Jamie Loftus) from 2022-02-22T00:21:35.193951

"On what date do you reveal you're a merperson?"

Comedian and TV writer Jamie Loftus (Robot Chicken, host of The Bechdel Cast) theorizes what it must be like being broken up but quarantine...

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Why Won
Doing Your Own Hair (w/ Tawny Newsome) from 2022-02-22T00:21:35.193114

Comedian Tawny Newsome (Space Force) chats with Nicole about learning how to do your own hair in quarantine, their crazy fashion phases, and the current state of "Zoom dating" along with the crazy ...

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Why Won
Butt Stuff (w/ Monét X Change) from 2022-02-22T00:21:35.185544

Drag queen Monét X Change (RuPaul's Drag Race, winner of RuPaul's Drag Race All Stars S4) shares the story about how they got their first STD from a race chaser, breaking up with their partner on T...

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Why Won
Dating with Disability (w/ Santina Muha) from 2022-02-22T00:21:35.159460

Actress and comedian Santina Muha (One Day at a Time, Curb Your Enthusiasm) answers the worst questions to ask someone in a wheelchair, shares some of the aggressive messages she's received on dati...

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Why Won
Fatphobia (w/ Roxane Gay) from 2022-02-22T00:21:35.154787

Oh boy this is a juicy one. Author Roxane Gay (Bad Feminist, Hunger) joins Nicole to discuss their experiences with institutional racism, dealing with fatphobia in interviews, and how she treated s...

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Why Won
Signs He's Into You (w/ Yassir Lester) from 2022-02-22T00:21:35.147522

It's our longest episode ever! Comedian Yassir Lester (Black Monday, Duncanville) joins Nicole to discuss sex protocol for a COVID era, reconnecting with old flings, body modifications, Yassir's Je...

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Why Won
Rock Bottom (w/ Sydnee Washington) from 2022-02-22T00:21:35.146415

Comedian and actress Sydnee Washington (Broad City, Gayme Show) joins Nicole to discuss feel-good foods to eat when you're sad, their lowest points in life, finding love on Instagram, and setting b...

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Why Won
Trash TV (w/ Patti Harrison) from 2022-02-22T00:21:35.142594

Comedian Patti Harrison (Shrill, Search Party) joins Nicole to chat about 90 Day Fiancé, issues with casting in today's media, and advocates for the well-being of child actors. Plus, they discuss t...

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Why Won
Healthcare (w/ Langston Kerman) from 2022-02-22T00:21:35.138972

Actor and comedian Langston Kerman (Insecure, The Boys) joins Nicole to discuss her recent broken ankle and awkward brush with healthcare. He also shares the perks of dating long distance, how to a...

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Why Won
Lining Up a Relationship for the End of the World (w/ Niccole Thurman) from 2022-02-22T00:21:35.101305

Comedian & actress Niccole Thurman (A Black Lady Sketch Show, Shrill) joins Nicole to discuss their 2021 resolutions, how they are cleaning out toxic negativity in their life, and review each other...

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Why Won
Sex Work (w/ AM Davies) from 2022-02-22T00:21:35.100496

Sex worker AM Davies (Host of Yes, A Strippper Podcast) is here to answer all of Nicole's questions about stripping and sex work. She discusses the difference between decriminalizing vs legalizing ...

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Why Won
Ask Him About His Credit Score (w/ Tiffany Haddish) from 2022-02-22T00:21:35.096820

Actress and comedian Tiffany Haddish (Girls Trip, Night School) first clears the air regarding her Clubhouse bullying allegations. Then, she talks about how dating has changed since Girls Trip, how...

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Why Won
Unravelling From A Breakup (w/ Rhea Butcher) from 2022-02-22T00:21:35.093077

Comedian Rhea Butcher (Adam Ruins Everything, Good Trouble) chats with Nicole about how they quit smoking after 16 years, being a lifetime vegetarian, and their old stand-up show, Put Your Hands To...

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Why Won
Arranged Marriages (w/ Hari Kondabolu) from 2022-02-22T00:21:35.084230

Stand-up comedian Hari Kondabolu (The Problem with Apu, host of Politically Re-Active) joins Nicole to break down some common misconceptions about arranged marriages, shares how he met his wife on ...

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Why Won
Deputy Gangs in the LA County Sheriff's Department (w/ Cerise Castle) from 2022-02-22T00:21:35.083400

In this bonus episode, Nicole talks to reporter Cerise Castle about her multi-part series, A TRADITION OF VIOLENCE, uncovering the history of deputy gangs in the LA County Sheriff's Department.
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Why Won
Finding the G-Spot (w/ Marc Rebillet) from 2022-02-22T00:21:35.075565

Loop Daddy AKA Marc Rebillet  Fucks. He and Nicole have a very horny chat about how he's enjoying his singledom, gaining the confidence to dominate submissive women, and why being brutally honest i...

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Why Won
Filming Sex Scenes (w/ Casey Wilson) from 2022-02-22T00:21:35.071768

Comedian Casey Wilson (Happy Endings, SNL) chats with Nicole about shooting her recent sex scene, exchanges crazy nannying stories, and shares how she met her husband on the set of Happy Endings. P...

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Why Won
Back in the Dating Game (w/ Shea Couleé) from 2022-02-22T00:21:35.068114

Drag queen Shea Couleé (Winner of RPDR All Stars 5) talks to Nicole about finding love at the club, being a drag mother, wig mishaps, and doing poppers. Plus, Nicole's back in the dating game and i...

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Why Won
The Power of 'I Love You' (w/ Sam Richardson) from 2022-02-22T00:21:35.065254

Actor and comedian Sam Richardson (Veep, I Think You Should Leave) chats with Nicole about his success finding love on Raya, wanting kids so he can continue doing kid things, the power of saying 'I...

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Why Won
The Cost of Being 'Cute' (w/ Cat Hollis) from 2022-02-22T00:21:35.064380

Cat Hollis led the 2020 Portland Stripper Strike. Here, she explain why it happened and her work for equitable workspaces in the adult industry. Cat discusses the costs of being cute, shares the co...

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Why Won
How to be Intuitive About Your Love Life (w/ Laura Day) from 2022-02-22T00:21:35.060735

'Psychic to the stars' and best selling author Laura Day is here to teach Nicole all about intuition and how to develop it. She discusses how she realized she had intuitive powers, coaches how to b...

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Why Won
Catfish Catcher (w/ Justin Martindale) from 2022-02-22T00:21:35.057066

Comedian Justin Martindale joins Nicole to discuss how their 'summer of love' has been disappointingly dry for the both of them. Justin shares the time he got catfished by a cop, how he deals with ...

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Why Won
Yelp for Escorts (w/ Alexa Eason) from 2022-02-22T00:21:35.056226

Full-service sex worker Alexa Eason shares about her life as an escort. She teaches Nicole about BDSM, the relationship risks involved with sex work, Instagram's censoring of fat bodies, and the dr...

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Why Won
Pooping Together (w/ Meghan Trainor and Ryan Trainor) from 2022-02-22T00:21:35.053411

Does the couple that poop together, stay together? Grammy-award winning singer-songwriter Meghan Trainor and brother Ryan Trainor (co-hosts of Workin on It') discuss the special relationship that's...

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Why Won
Second Puberty (w/ Carter Ray) from 2022-02-22T00:21:35.052537

Filmmaker Carter Ray (The Change Up) chats with Nicole about their experience going through a 2nd puberty while on hormones, the challenges they faced coming out while attending a Christian high sc...

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Why Won
From DM to Marriage (w/ Shannon Joy Rodgers) from 2022-02-22T00:21:35.000359

Friend and writer Shannon Joy Rodgers (Jimmy Kimmel Live!, Ellen) joins Nicole to talk about roller-blading, the costs and challenges of planning a COVID-safe wedding right now, and how she found h...

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Why Won
My Dominatrix Roommate (w/ Joyelle Nicole Johnson) from 2022-02-22T00:21:34.996697

Comedian Joyelle Nicole Johnson lived with a dominatrix. She talks about the type of clients that would visit her apartment, and the kinky 'services' she was offered. Plus, she shares how she met h...

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Why Won
Hot Singles In Your Area (w/ Chelsea Peretti) from 2022-02-22T00:21:34.992454

Comedian and actress Chelsea Peretti (Brooklyn Nine-Nine, Sing 2) chats with Nicole about the best places you can go to meet singles, strong pick-up lines, and how she met husband Jordan Peele thr...

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Why Won
Lesbianity (w/ Gina Yashere) from 2022-02-22T00:21:34.983820

Comedian Gina Yashere (The Daily Show, Bob Hearts Abishola) chats with Nicole about the adorable meet-cute story behind meeting her girlfriend at a women's festival. She also discusses the process ...

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Why Won
Love Exhibited (w/ Moses Storm) from 2022-02-18T09:00

Comedian Moses Storm lived in an art exhibit where he would sleep, shit, and had sex in front of an audience.  He navigates trying to fi...

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Dick Tricks (w/ Shalita Grant) from 2022-02-11T09:00

Actress Shalita Grant (You, NCIS: New Orleans) talks to Nicole about life dating an MMA fighter, her straight sex phrase, the moment she realized she was a natural at lesbian sex, and how her inte...

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Why Won
Cumbucha (w/ Lamorne Morris) from 2022-01-28T09:00

Actor and comedian Lamorne Morris (New Girl, Woke) is here! Lamorne teaches Nicole about the importance of playing hard to get, and how to act unavailable to attract a man. They read a listener's s...

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Why Won
How to Make a Man Commit (w/ Abbi Jacobson) from 2022-01-21T09:00

Comedian and actress Abbi Jacobson (Broad City, The Mitchells vs the Machines) and Nicole go over a list of ways to make a man commit - is the advice solid or is it all just mind games? Plus, Abbi ...

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Why Won
Throwing Shade (w/ Bianca Del Rio) from 2022-01-14T05:00

Drag queen icon Bianca Del Rio (winner of Drag Race S6) joins Nicole to chat about the challenges of finding a partner who fits with your lifestyle, the smart system behind her meet-and-greets, get...

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Why Won
Relationship Deal Breakers (w/ Nina West) from 2021-12-31T09:00

Drag queen Nina West (Drag Race S11, Hairspray) is just as tragically single as Nicole. They commiserate over the single life, talk about how Nina’s life drastically changed after Drag Race, the mo...

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Why Won
Naming Your Body Parts (w/ Heidi N Closet) from 2021-12-24T09:00

Drag queen Heidi N Closet (RuPaul's Drag Race S12) chats with Nicole about how her dating life changed after Drag Race, the kinky things she's introduced in the bedroom, the various names she's giv...

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Why Won
Raw, Unadulterated Fun (w/ D'Arcy Carden) from 2021-12-17T09:00

Friend, actress, and comedian D’Arcy Carden (The Good Place, Barry) joins Nicole live for some raw, unadulterated fun! They check in on how they've been handling the pandemie, the adorable details ...

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Why Won
The Nicest Dick I've Ever Seen (w/ Naomi Smalls) from 2021-12-10T09:00

The holidays are here! As a gift, we're releasing the livestreamed episodes from behind the paywall! On today's episode, drag queen Naomi Smalls (RuPaul's Drag Race S8, All-Stars S4) joins Nicole ...

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Why Won
Best Relationship Ever! (w/ Jimmy O. Yang) from 2021-11-26T09:00

Comedian and actor Jimmy O. Yang (Silicon Valley, Love Hard) joins Nicole to tell the story of how he met his girlfriend, discusses at what point does a relationship become serious, and suggests Ni...

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Why Won
Kidnapped and On the Run (w/ Aida Rodriguez) from 2021-11-19T09:00

Comedian Aida Rodriguez was kidnapped twice as a child. She describes her time on the run with a murderer, and how she uses her stand-up comedy to process her traumas. They also discuss dating red...

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Why Won
Real Life vs Your Persona Life (w/ Raven-Symoné and Miranda Maday) from 2021-11-12T09:00

Raven-Symoné (That's So Raven) and wife Miranda Maday join Nicole to share the story of how they met, broke up, and got back together again. They discuss learning to love your real self as well as ...

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Why Won
The Art of Taking a Profile Pic (w/ Rob Corddry) from 2021-10-29T08:00

Comedian Rob Corddry (Childrens Hospital, Hot Tub Time Machine) joins Nicole to discuss cannibalism, the art of taking a good profile picture, Rob gives advice on Nicole's dating app bio, and they ...

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Why Won
Zoom Speed Dating (w/ Gilli Nissim) from 2021-10-22T08:00

Friend and writer Gilli Nissim (The Other Two, A.P Bio) joins Nicole to discuss breaking up in the middle of the pandemic, her experience speed dating over Zoom, and traveling abroad for hookups. ...

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Why Won
Attached (w/ Brittani Nichols) from 2021-10-15T08:00

Comedian and writer Brittani Nichols (A Black Lady Sketch Show) chats with Nicole about recognizing different adult attachment styles in relationships, how her relationship sparked by a DM slide as...

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Awkward Sex Talk (w/ Crystal Methyd) from 2021-09-24T10:00

Drag queen Crystal Methyd (RuPaul's Drag Race S12) joins Nicole to chat about their most romantic date, getting the 'sex talk' at the age of 22, and debates if you should text your date back immedi...

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Why Won
Playing Hard to Get (w/ Ms. Pat) from 2021-09-17T18:00

Comedian Ms. Pat chats with Nicole about her time in jail for drug trafficking, shares the secrets behind her 28 years of marriage, and offers advice on how to play hard to get. Plus, Ms. Pat's not...

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Sucking D in the Locker Room (w/ Laganja Estranja) from 2021-08-27T09:00

Drag queen and choreographer Laganja Estranja (RuPaul'sDrag Race S6) joins Nicole to discuss her truth coming out as trans, finding confidence in self-love, the thrill of sucking dick in the high s...

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Why Won
Hot Girl Summer (w/ Lawrence Chaney) from 2021-08-20T09:00

Drag queen of Scots Lawrence Chaney (winner of RPDR UK S2) chats with Nicole about his dating live after winning Drag Race, how he got banned from Tinder for 'catfishing' as himself, and pitches to...

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I got 99 problems... palsy is just one (w/ Maysoon Zayid) from 2021-08-13T09:00

Comedian and actress Maysoon Zayid was born with cerebral palsy. She chats with Nicole about some of the cruel comments she receives about her disability, the struggles comedians of color face in H...

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Why Won
Problem Solving on the Toilet (w/ Yola) from 2021-07-30T09:00

What a treat. Grammy nominated English musician Yola is here! Nicole and Yola chat about the difference in racism when dating in the UK vs the US, how crying on her motorcycle back from her mother'...

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Why Won
Thriving Alone (w/ Harvey Guillén) from 2021-07-23T09:00

Actor Harvey Guillén (What We Do in the Shadows) is single but not quite ready to mingle. He discusses why he guards his profession from his dating life, how he found love on Instagram, and the imp...

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Why Won
Being a Single Mom of 3 (w/ Francesca Amber) from 2021-07-16T09:00

Nicole’s close friend Francesca Amber (host of Law of Attraction Changed my Life) talks about the struggles of being a mother of twins, explains the latest fad of 'co-parenting', and describes how ...

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Why Won
Are you 'Love Avoidant'? (w/ Reggie Watts) from 2021-06-25T09:00

Comedian and musician Reggie Watts (The Late Late Show with James Corden) chats with Nicole about his unique eating habits, his time spent playing in a 70's cover band, and the weird shift from bei...

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Why Won
We're living in the wildest times (w/ Jason Concepcion) from 2021-06-18T09:00

Jason Concepcion (host of Takeline, Binge Mode) joins Nicole to discuss the culture shock he experienced visiting the Philippines during a coup, how the pandemic revealed America's systemic failure...

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Why Won
Interview with a Male Escort (w/ Troy Amistadi) from 2021-06-11T09:00

International male escort Troy Amistadi is here to answer all of Nicole's questions about escorting and sex work. He discusses how the TV show Gigolos inspired him to get into the business, the par...

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Why Won
Sleeping with your Uber Driver (w/ London Hughes) from 2021-05-28T09:00

Comedian London Hughes (Netflix's To Catch a Dick) and Nicole chat about her experience moving to America during a pandemic and race war, sleeping with her Uber driver, doggy style techniques, suck...

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Proposal Gone Wrong (w/ Paul Scheer) from 2021-05-21T09:00

Comedian and actor Paul Scheer (The League, Black Monday) and Nicole chat about how his proposal to June Diane Raphael went terribly wrong, how June's wedding ring was stolen from her finger, and s...

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Kinky in Public (w/ Jessica Rothe) from 2021-05-14T09:00

Actress Jessica Rothe (Happy Death Day, La La Land) and Nicole discuss if it's OK to do kinky acts in public, the bizarre ways people are monetizing kinks, and the surprising reality of male escort...

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Why Won
Being 'Sexually Smart' (w/ JB Smoove) from 2021-04-30T09:00

Comedian, actor, and self-proclaimed 'Love Doctor' JB Smoove (Curb Your Enthusiasm) joins Nicole to provide his wisdom on flirting, roller skating, developing rhythm, and shares his guide on having...

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Bad Dating App Bios (w/ Aparna Nancherla) from 2021-04-23T09:00

Stand-up comedian Aparna Nancherla (BoJack Horseman, Corporate) joins Nicole to discuss how her first and only Tinder date evolved into her longterm relationship. They read some bad dating app bios...

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Will You Be My Girl? (w/ Jillian Bell) from 2021-04-16T09:00

Actress and comedian Jillian Bell (Workaholics,The Pole) joins Nicole to solve the reasoning behind their mutual singleness. They discuss the results of their recent psychic readings, how they conf...

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Acid Tripping (w/ Bowen Yang) from 2021-03-26T09:00

Actor and comedian Bowen Yang (SNL) is just as fiercely single as Nicole. They talk about the struggles of singledom, the crazy current news cycles, their acid tripping experiences, and Bowen share...

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Polyamorous and Experimenting (w/ Ashley Ray) from 2021-03-19T09:00

Comedian and pop culture expert Ashley Ray (host of TV I Say podcast) used Tinder to run an experiment where she dated every zodiac sign for a month at a time. She explains her findings, her polyam...

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Why Won
How to Manifest your Dream Man (w/ Alaska Thunderfuck) from 2021-03-12T10:00

Drag queen Alaska Thunderfuck (RuPaul's Drag Race S5, winner of Drag Race All Stars S2) joins Nicole to discuss what it was like to date another drag queen, how to manifest your dream man, their un...

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You Need Therapy (w/ Nore Davis) from 2021-02-26T10:00

Comedian Nore Davis talks with Nicole about the movies that have brought them joy, why he's decided to 'date himself', leaving a toxic relationship, and the importance of therapy.

This Bla...

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Love & Music (w/ Randy Jackson) from 2021-02-19T10:00

Musician/producer/host Randy Jackson (American Idol, Name That Tune) shares his skepticism with app dating, the worst date he’s been on, his favorite love songs, and catfishing.

This Black...

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Stripping & Sex Work (w/ Teddy B. Ruxpin) from 2021-02-12T10:00

Dancer and sex worker Teddy B. Ruxpin chats with Nicole about all things stripping and sex work. They discuss her start into the profession, finding her niche as an "alt girl", dealing with racism ...

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Dating as a Virgin in your 30s (w/ Jake Kroeger) from 2021-01-31T22:10:42.023393

Dating in your thirties can be nightmarish. Jake Kroeger (Stand-up, The Comedy Bureau) shares his experiences navigating the dating scene as a virgin, the cute story behind his first kiss at the ag...

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Married at 20 (w/ Ron Funches) from 2021-01-31T22:10:42.023393

"We stayed married for 7 years - and we should've never gotten married." From the age of 20, Ron Funches (Trolls, Giggle Fit, The Eric Andre Show) was married with a son. He shares his struggles b...

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Microdosing (w/ Johnny Pemberton) from 2021-01-31T22:10:42.023393

"I thought I was going to die. I was actually laughing at the idea of living." Johnny Pemberton (22 Jump Street, Superstore) discusses taking LSD at Disneyland, and accidentally overdosing while t...

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Having Sex in Drag (LIVE from DragCon 2019 w/ Vicky Vox) from 2021-01-31T22:10:42.023393

Drag queen Vicky Vox (DWV, Magic Mike XXL) joins Nicole to discuss having sex in drag, using AOL messenger to lose your virginity, and where to find the biggest dicks. Nicole had sex with a Canadia...

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Wes from Nailed It is here! from 2021-01-31T22:10:42.023393

Weston Bahr is on the podcast to discuss what it's like to be harassed by Nicole on Nailed It, creepy DMs he gets from fans, all the dick jokes they've had to cut from the show, and so much more in...

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Owning Your Sexuality (w/ Margaret Cho) from 2021-01-29T10:00

Comedian Margaret Cho (The Masked Singer, All-American Girl) and Nicole chat about claiming your right to talk about sexuality, her experience coming out as queer, learning Japanese bondage, and ho...

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Empowering Relationship Statements (w/ Deon Cole) from 2021-01-22T10:00

Actor and comedian Deon Cole (Black-ish, Barbershop) joins Nicole to share his deep wisdom about love and relationships. They discuss judging people by the moment, recognizing if your partner is in...

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Why Won
Big Dick Energy (w/ Conan O'Brien) from 2021-01-15T10:00

Conan O'Brien is here to help solve the root problems behind Nicole's singledom. They also discuss his sexually repressed Catholic upbringing, what it's like to have Big Dick Energy, and his plans ...

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Why Won
Wedding Ruiners (w/ Solomon Georgio) from 2020-12-25T10:00

Stand-up comedian and #Skategang member Solomon Georgio (Shrill, Adam Ruins Everything) talks to Nicole about his recent butt surgery and how he's been adapting to his new butt. They also chat abou...

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Why Won
Issues Affecting the Black Condition (w/ Roy Wood Jr.) from 2020-12-18T10:00

Roy Wood Jr. (The Daily Show) shares his calculations on the safest way of traveling during COVID, discusses dealing with friends who aren't taking the pandemic seriously, getting detained in Canad...

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Caught in the Act (w/ Jiggly Caliente) from 2020-12-11T10:00

Drag queen and actress Jiggly Caliente (RuPaul's Drag Race S4, Broad City) joins Nicole to discuss sex work, walking in on friends or family members having sex, "Dick on-demand boys", and how much ...

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Why Won
Serving the Full Fantasy (w/ Creme Fatale) from 2020-11-27T21:59:04

Drag queen & makeup artist Creme Fatale joins Nicole to discuss dating horror stories, how to leave a bad date fast, why aren't there any lady gloryholes, and makeup.

Check out Creme Fetal...

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Why Won
Grown-Up Breakup (w/ Lucy Stoole) from 2020-11-20T10:00

Drag queen Lucy Stoole joins Nicole to discuss the story behind their drag name, their recent breakup, the struggles of dating app messaging, and if it's okay to leave a bad date early.

Su...

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Why Won
Fresh Heartbreak (w/ Priyanka) from 2020-11-13T10:00

Drag queen Priyanka (Winner of Canada's Drag Race, host of YTV's The Zone) joins Nicole to discuss their very recent breakup, getting COVID19 from Brooke Lynn Hytes, evolving from a kids tv host to...

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Why Won
Volunteering in Your Community (w/ Mitra Jouhari) from 2020-10-30T09:00

Comedian Mitra Jouhari (Big Mouth, Three Busy Debras, host of Urgent Care) joins Nicole to discuss missing malls, the horrors of dating in high school, awkward Zoom auditions, and reminisce about t...

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Why Won
Advice from a Dating Coach (w/ Damona Hoffman) from 2020-10-23T09:00

Dating coach Damona Hoffman (A&E Network's #BlackLove, A Question of Love) is here to dish some professional advice. She shares tips for video-dating, setting up your dating app profile, how to sta...

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Why Won
We're Thirsty (w/ Nichole Perkins) from 2020-10-16T09:00

Writer and podcaster Nichole Perkins (Thirst Aid Kit) joins Nicole to discuss setting boundaries in your casual relationships, dealing with thirsty groupies, and, can you get COVID from your pussy?...

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Why Won
Joking Around (w/ Yamaneika Saunders) from 2020-09-25T09:00

The incredibly funny Yamaneika Saunders (Broad City, Inside Amy Schumer) joins Nicole to discuss comedy, following her mom's love for stand-up, her defense for humor about people with disabilities,...

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Why Won
From Race Chaser to Husband (w/ Latrice Royale) from 2020-09-18T09:41:27

Drag queen Latrice Royale (RuPaul's Drag Race, RuPaul's Drag Race All Stars) joins Nicole for a good teeheehee. She discusses getting into drag on a dare, writing on AJ and the Queen, meeting their...

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Why Won
America Scammed Us (w/ Dewayne Perkins) from 2020-09-11T09:00

Comedian and writer Dewayne Perkins (Brooklyn Nine-Nine, The Break with Michelle Wolf) joins Nicole to talk about getting back together with his ex, the importance of checking in with your partner,...

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Why Won
The World is Really Shitty and I'm Alone (w/ Ziwe) from 2020-08-28T09:00

Ziwe (writer for Desus & Mero) and Nicole chat about being horn'd up, what they've been crying over, and are trying to learn to love what they see in the mirror. Nicole's back on the apps, where it...

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Why Won
Class Clown on the Plantation (w/ Amber Ruffin) from 2020-08-21T09:00

Writer and actress Amber Ruffin(Late Night with Seth Meyers, A Black Lady Sketch Show) chats with Nicole about the weight of having to discuss politics on Late Night, how they can make racism funny...

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Why Won
Code-Switching (w/ Gabby Sidibe) from 2020-08-14T09:00

Gabby Sidibe (Precious, American Horror Story, Empire) joins Nicole to discuss the problematic expectation to have to code switch at work, why Black women are often dealbreakers for Black men, and ...

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Why Won
Performative Allies (w/ Jeffrey Bowyer-Chapman) from 2020-07-31T07:00

'Do you want to be an active ally, or do you just want to say that out loud?'

Jeffrey Bowyer-Chapman (Judge/host on Canada's Drag Race, Unreal) joins Nicole to unpack racial traumas from c...

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Why Won
White-Passing Privilege (w/ Ele Woods) from 2020-07-24T07:00

Actress/comedian Ele Woods (The Good Place, CollegeHumor) shares her experiences being White-passing, and how she's using it for good. Her and Nicole discuss rollerblading and sewing in quarantine,...

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Why Won
Sleeping for the Story (w/ The Vixen) from 2020-07-17T07:00

Drag queen The Vixen (Rupaul's Drag Race S10, host of Black Girl Magic) chats about calling out microaggressions on Drag Race, the type of hate mail they receive, and how appearing on the show lead...

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Why Won
Black History Year (w/ Bob the Drag Queen) from 2020-07-10T07:00

"I was just looking for butthole. And then wrapped around the butthole was a really nice, young, Jewish man."

Bob the Drag Queen (winner of RuPaul's Drag Race S8) chats about systematic ra...

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Why Won
If You See It, You Can Be It (w/ Kirby Howell-Baptiste) from 2020-06-26T07:00

Actress Kirby Howell-Baptiste (The Good Place, Barry, Why Women Kill) discusses the rise in "Karens", managing life after death, and the reality of the Black experience. Plus, they share personal s...

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Why Won
Foundations of a Successful Relationship (w/ AJA) from 2020-06-19T07:00

Rapper and former drag queen AJA (RuPaul's Drag Race S9, All Stars S3) catches up with Nicole on the #BlackLivesMatter protests, discussing Black history erasure and how people can be a good ally i...

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Why Won
How to Date Virtually (w/ Jinkx Monsoon) from 2020-06-12T07:00

"Sex is always better when you can be yourself during it"

Jinkx Monsoon (Winner of Rupaul's Drag Race S5) dishes about fulfilling race chaser fantasies, heteronormative roleplay, how their...

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Why Won
Embrace Your Sloppy (w/ Michelle Buteau) from 2020-05-29T07:00

The wonderful comedian Michelle Buteau (Always Be My Maybe, host of The Circle) discusses owning her sexuality, raising twins, being denied the ability to adopt kids, and so much more. Nicole and M...

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Why Won
Don't Comment on my Body (w/ BenDeLaCreme) from 2020-05-22T05:00

BenDeLaCreme (RuPaul's Drag Race, RPDR All Stars) chats about how he deals with other people's traumas, getting gaslight by their therapist, and whats it's like to move in with a new boyfriend righ...

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Why Won
Fast n' Friendly Divorce (w/ Giulia Rozzi) from 2020-05-15T07:00

Oh boy, this episode is a juicy one. Comedian/actress Giulia Rozzi (Girl Code) speaks to Nicole about the struggles of being pregnant in quarantine, if she has any worries about raising a bi-racial...

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Why Won
Instagram DM Sex (w/ Ira Madison III) from 2020-04-24T07:30

Ira Madison III (TV writer, host of Keep It) chats about how he's staying sane while quarantine alone, his guest appearance on You, and how he's having sex over Instagram.

For more Nicole ...

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Why Won
Third Wheel in a Quarantine (w/ Tommy Lenk) from 2020-04-17T07:00

"Marriage should be a lease with an option to renew"

Tommy Lenk (Buffy the Vampire Slayer, host of Trashcast) shares his ideas to modernize marriage, points out the archaic rules of straig...

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Why Won
Saying Yes to the Dress (w/ Megan Gailey) from 2020-04-10T07:00

Comedian Megan Gailey (Conan, Tonight Show Starring Jimmy Fallon) chats with Nicole about life as a newlywed in quarantine, the horrors of wedding dress shopping, and the freaks using dating apps r...

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Why Won
Dating During Coronavirus (w/ Jacquis Neal) from 2020-03-27T08:00

"We're all just on Zoom trying to date people?"

Jacquis Neal (host of Culture Kings) joins us remotely while in quarantine to discuss what it's like being cooped up with your S/O in isolat...

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Why Won
Love (w/ Paul Rust) from 2020-03-20T08:00

Paul Rust (Love, Comedy Bang! Bang!, Arrested Development) has been married for 5 years. He discusses what it's like to date and work with his partner, the differences between his show 'Love' and h...

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Why Won
Recognizing your Self-Worth (w/ Nicolette Mason) from 2020-03-13T08:00

"Everyone that I thought was 'the one', was a piece of trash."

Nicolette Mason (plus-size fashion blogger) joins Nicole to discuss the latest dating buzzwords of 2020, reflecting on your s...

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Why Won
Seeking Single Men at Target (w/ Janelle James) from 2020-02-28T09:00

Janelle James (stand-up, writer for Black Mondays) joins Nicole to discuss the difference between East coast and West coast men, when to let a guy see you without makeup, and the best time to find ...

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Why Won
Unpacking Nicole's Fear of Relationships (w/ Jess Rona) from 2020-02-21T09:00

"Once both people like each other, the games are over."

Close friend and dog groomer Jess Rona (Author of Groomed) has a heart-to-heart with Nicole to unpack her fears of being in a relati...

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Why Won
Finding Love at DragCon (w/ Taylor Orear) from 2020-02-14T15:47

Friend and fashion stylist Taylor Orear joins Nicole to shares the most adorable story behind meeting his boyfriend at RuPaul's Drag Con. They also discuss the importance of leaving baggage behind ...

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Why Won
Setting 2020 Resolutions (w/ Kevin T. Porter) from 2020-01-31T09:00

Podcast pro Kevin Porter (Host of Inside Voices, Good Christian Fun, and Gilmore Guyspodcast) helps Nicole set some 2020 dating goals - starting with deleting her Raya app. They also identify her n...

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Why Won
Hiring a Professional Matchmaker (w/ Grace Edwards) from 2020-01-24T10:00

Nicole's old roommate Grace Edwards (writer - Unbreakable Kimmy Schmidt, Loosely Exactly Nicole) answers Nicole's questions about professional matchmaking and shares the challenges of dating 3 men ...

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Why Won
Prison Dating (w/ Ann Pyne) from 2020-01-17T10:00

"He had committed arson when he tried to kill himself in his mother's basement"

Ann Pyne (Drag queen booker) is the queen of drag queens. She discusses being a daily drinker since she was ...

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Why Won
Dead Mom Club (w/ Kate Spencer) from 2020-01-10T10:00

Kate Spencer (Forever 35 podcast, author of Dead Mom's Club) discusses Nicole Byer's mention in The Masked Singer, explains to Nicole what a "VSCO Girl" is, and discusses life after losing a parent...

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Why Won
Vehicular Assault (w/ Akilah Hughes) from 2019-12-27T10:00

Akilah Hughes (host of What a Day podcast) discusses why she doesn't believe in long term relationships, shares her worst date stories, and the time she cut all her toes during sex. Nicole fears fo...

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Why Won
Moving On After a Nasty Breakup (w/ Marty Michael) from 2019-12-20T10:00

Nicole starts the episode with a DM from her doppelgänger who's been taking advantage of her likeness. Marty Michael (Co-Founder of Headgum) shares a wild first date he had with a girl who's life w...

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Why Won
Emojis are a Red Flag (w/ Whitney Cummings) from 2019-12-13T10:00

"We're taught to laugh at guys' jokes that aren't funny so they don't feel insecure."

Whitney Cummings (stand-up, creator of Two Broke Girls) explains why she likes to be the beta in her r...

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Why Won
What's it Like to Finally Date a Good Guy (w/ Michaela Watkins) from 2019-11-29T09:00

Michaela Watkins (SNL, The Unicorn, Big Mouth) has been boy crazy her whole life. She discusses the hot kids they were into, shares why her husband proposed with a t-shirt, and her mom's "orgies" w...

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Why Won
Having Tandem Sex (w/ Sasheer Zamata) from 2019-11-22T09:00

"When you and your friend fuck at the same time, just in different places".

Best friend Sasheer Zamata (SNL, Corporate) shares the time her and Nicole tandem-fucked in Canada and why it wa...

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Why Won
A Nightmare Wedding Experience (w/ Diona Reasonover) from 2019-11-15T10:00

Diona Reasonover (NCIS, I Love You, America) shares her nightmare wedding experience which included a rear-end accident, a broken wrist, a typhoon, an ASOS wedding dress, and multiple wedding crash...

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Why Won
Overcoming Emotional Setbacks (w/ Echo Kellum) from 2019-10-18T09:00

"Please acknowledge your pain."

Echo Kellum (Arrow, Rick & Morty) discusses overcoming life's pain after emotional trauma, controlling negative feelings, and his experience practicing abst...

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Why Won
Managing Anxieties During Intimacy (w/ Dave Ross) from 2019-10-11T09:00

"I would eat my ass for flavor, and you can quote me on that."

Dave Ross (stand-up, Suicide Buddies podcast) shares his experience performing at a sex club, the story behind his first hand...

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Why Won
Breaking Up (w/ Paul F. Tompkins) from 2019-09-27T09:00

"I was at a point where I was like... I never sorta played the field and had fun. I'm gonna do that now."

Paul F. Tompkins (Between Two Ferns: The Movie, Threedom podcast) discusseshow he ...

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Why Won
Dating Neurodiversity (w/ Sam Pancake) from 2019-09-20T09:00

"He said, 'I'd rather be dead than how old YOU are.'"

Things get real emotional in this episode. Sam Pancake (Arrested Development, A Million Little Things) discusses dating people on the ...

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Why Won
Hooking up on Craigslist (w/ Atsuko Okatsuka) from 2019-09-13T08:00

Atsuko Okatsuka (stand-up, Let's Go Atsuko! podcast) discusses living as an undocumented for 7 years, meeting people on Craigslist, and being fetishized for her ethnicity. Plus, Nicole Byer shares ...

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Why Won
Problematic Issues of Porn (w/ Erika Lust) from 2019-08-30T08:00

"I would like to see films where women's pleasure is also in focus. Where it's important to the story that she is also having a good time."

Erotic film director, screenwriter, and producer...

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Why Won
Dating Dogs and Werewolfs (w/ Justin Simien) from 2019-08-16T08:00

"When he came, did he go AWOOO?"

Justin Simien (Creator of Dear White People) joins Nicole to talk about the kinkiest thing he's ever done, teach her about gay "puppy-pack" arrangements, a...

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Why Won
Making a Polyamorous Relationship Work (w/ DeRay Davis) from 2019-07-26T08:00

DeRay Davis (Snowfall, 21 Jump Street) has lived a polyamorous relationship with 2 women for most of his life. He explains how he introduces it to his partners, how to show respect to the parents, ...

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Why Won
A Boyfriend for Every Stage of your Life (w/ Jessica McKenna) from 2019-07-19T09:00

Jessica McKenna (Off Book podcast) has had a boyfriend in every stage of her life. She details the drama behind her middle school romance, to meeting boys in high school mock trial, and charming he...

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Why Won
The Opposite of a Meet-Cute (w/ Alice Wetterlund) from 2019-06-28T09:00

Alice Wetterlund (Girl Code, Treks and the City podcast) joins Nicole to discuss their Girl Code tour horror stories, talk about men who claim to have dated celebrities (we're talking about YOU, Mo...

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Why Won
Top or Bottom? (LIVE w/ Jon Gabrus, Nick Wiger, and Mike Mitchell) from 2019-06-21T09:00

Freshly drunk from a power-hour, Gabrus (High & Mighty), Nick Wiger and Mike Mitchell (Doughboys) join Nicole to discuss how they would want to die, their favorite sex positions, and if they like a...

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Why Won
How to Share Secrets on Drag Race (w/ Shangela) from 2019-06-14T07:00

D.J. 'Shangela' Pierce (RuPaul's Drag Race, A Star is Born) discusses his struggles with dating, getting picked up by fans, and describes his perfect partner. Plus, Shangela shares how drag queen s...

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Why Won
Dating in the 3rd Grade (w/ Beth Stelling) from 2019-05-24T09:00

Beth Stelling (Crashing, I Love You, America) discusses the crazy things they learned in school, what it was like to have a 3rd grade boyfriend, how she met her current boyfriend doing stand-up. Listen

Why Won
How to Date Long Distance (w/ Demi Adejuyigbe) from 2019-05-17T10:00

Demi Adejuyigbe (The Late Late Show with James Corden, Punch Up The Jam podcast) joins Nicole to discuss how he found love on Twitter, how to successfully date long distance, and at what point you ...

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Why Won
How to get Banned from Tinder (w/ Eleanor Bray) from 2019-05-10T04:00

Eleanor Bray (Nicole's old assistant!) comes on to discuss what it was like working as Nicole's assistant, how she got banned on Tinder, and the musicals they've performed in. They also share their...

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Why Won
Building a Sex Roster (w/ Laura and Rachel) from 2019-04-26T04:01

"You get a social security number when you're born, you should also get a therapist that you have to see when you turn 13."

Laura and Rachel (Girls on Porn podcast) teach Nicole how to cre...

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Why Won
High School Dating (w/ Cameron Esposito) from 2019-04-19T04:00

Cameron Esposito (Put Your Hands Together, Queery podcast) discusses what it's like to host a show with her ex-wife, her past experience working as a circus ring leader, and how it feels to get dum...

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Why Won
Getting an STI from Grindr (w/ Matt Rogers) from 2019-04-12T04:00

"If it got leaked - everyone would know that I'm really good at sucking dick."

Matt Rogers (Las Culturistas podcast) discuss their experiences with Scientology, what it's like being too "i...

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Why Won
Learning How to Love Yourself (w/ Charla Lauriston) from 2019-03-29T04:00

"Every black person I know is in therapy. And if they're not, I encourage them to be."

Charla Lauriston (Ghosted, People of Earth) dissects white privilege, how hard it is to be a black wo...

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Why Won
Blowjob Tips (w/ Jake and Amir) from 2019-03-22T04:30

Jake Hurwitz and Amir Blumenfeld (Jake and Amir) discuss their favorite porn, whether they like to 69, if they would enjoy sucking their own dick, the best lubes to masturbate with, and give some b...

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Why Won
Date Exit Strategy (w/ Grace Helbig and Mamrie Hart) from 2019-03-15T04:00

"Guys go on Raya just to see how famous of a person they can match with."

Grace Helbig and Mamrie Hart (This Might Get Weird podcast) discuss their go-to lies to get out of bad dates, shar...

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Why Won
Why You Need Couple's Therapy (w/ Naomi Ekperigin) from 2019-02-22T05:00

"There's nothing I love more than a slutty wedding vibe"

Naomi Ekperigin (Broad City) shares her experience dating on Craigslist, why every couple should go to couple's therapy. Nicole des...

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Why Won
Eskimo Sisters (w/ Skyler Hurt) from 2019-02-15T05:00

Nicole met Skyler through Tinder, and they turned out to be eskimo sisters. Things got weird in their relationship real fast when Nicole began dating her ex-boyfriend's ex-girlfriend - without him ...

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Why Won
All Things Panties (w/ Eliot Glazer) from 2019-01-25T05:01

Eliot Glazer (Broad City, New Girl) discusses spending money on nice underwear for your partner, the grimiest requests he's received on dates, and how people need to set boundaries in and out of a ...

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Why Won
Role-Playing (w/ Rachel Bloom) from 2019-01-18T05:00

"Good role-playing is just bad improv"

Rachel Bloom (Crazy Ex-Girlfriend) has an open discussion about finding therapy and using medication to treat mental health. She also discusses why i...

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Why Won
Seeking Professional Advice (w/ Dr. Chris Donaghue) from 2019-01-11T08:00

Dr. Chris Donaghue (Host of Loveline, sex and relationship therapist) provides Nicole with an honest assessment why she may be single. He provides her relationship advice and a Tinder bio makeover....

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Why Won
Scheduling Your Booty Calls (w/ Raiza Licea) from 2018-12-28T05:00

"If you're busy, you need to book a dick appointment"

Raiza Licea (UCB) agrees that life is busy and sometimes you just gotta book time for a dicking. Nicole goes on a wild date with her L...

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Why Won
Dating Gay Twins (w/ Joel Kim Booster) from 2018-12-21T05:00

"I was apart of an orgy on a ship, where I looked over at my friend who was wearing this guy like a fucking bracelet"

Joel Kim Booster joins Nicole to discuss their favorite porn narrative...

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Why Won
Getting Past Dick Size (w/ Lisa Hanawalt) from 2018-12-14T05:00

"He just started sweating so much, that it was like water pouring onto me. And he said it was cause he was sad about his ex-girlfriend."

Lisa Hanawalt (Bojack Horseman, Baby GenuisesPodcas...

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Why Won
Nicole Does a Live Tarot Reading (w/ Inessa Frantowski) from 2018-11-30T05:00

Inessa Frantowski (UCB) performs a live tarot reading for Nicole, and boy, are the results dark. They also discuss at what point in the relationship do you have 'the talk', and changing yourself to...

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Why Won
Dating for Personality or Looks (w/ Erin Whitehead) from 2018-11-23T05:00

"The thought of you inside me makes me upset"

Erin Whitehead (Animals, Wild Horses) shares her experiences on a dating app designed for Apple fans, why she doesn't like relationships, and ...

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Why Won
Nicole Reviews Guy Fieri's Restaurant at the Burbank Airport (w/ Justin Noble) from 2018-11-16T05:00

"This is the best date I've ever planned, and it's all downhill from here."

Nicole opens up about her current dating life! She shares the story of her best date ever at Guy Fieri's restaur...

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Why Won
Sex Tips to Make Your Girl Cum (w/ Ify Nwadiwe) from 2018-10-26T04:00

"I promise you, you'll never fuck good enough to not have to eat pussy"

Ify Nwadiwe (@midnight, Buzzfeed Video, Nerdificent Podcast) joins us to discuss playing D&D with the Sprouse twins,...

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Why Won
Ice Cold Kiss (w/ Tony Rodriguez) from 2018-10-19T04:00

Tony Rodriguez (UCB) discusses his worst dates, the importance of communication during sex, and bad kissing. Nicole shares the time she showed her pussy to her roommate.

You can play along...

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Why Won
Limp Dick (w/ Pandora Boxx) from 2018-10-12T04:00

Pandora Boxx (RuPaul's Drag Race S2) discusses life after Drag Race, being in an open relationship, and wild fan encounters. Nicole describes her latest nightmare date filled with red flags.
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Why Won
The Trouble with Threesomes (w/ Jazzmyne Robbins) from 2018-09-28T04:00

Jazzmyne Robbins (Buzzfeed) is on to discuss thirsting publicly on Instagram, the times they’ve contemplated sleeping with fans, and the problematic nature of threesomes.

You can play alon...

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Why Won
Sex Tapes (w/ Roz Drezfalez) from 2018-09-21T16:34:18

Roz Drezfalez (Drag queen, stand-up) discusses the life and struggles of dating as a drag queen. Nicole expresses why dating a improv comic is a turn off for her, and shares her interest in having ...

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Why Won
Nicole Plays Matchmaker (w/ Jason Kim) from 2018-09-14T04:00

Jason Kim (Love, Girls) is on the podcast. They talk about how they met over a mutual love for Beyoncé, Nicole shares her latest cocaine bender, and describes the turn of events that lead her to lo...

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Why Won
Woke Therapy (w/ Fiona Landers) from 2018-08-31T04:00

Things get heavy in this episode of Why Won't You Date Me. Fiona Landers (UCB, Full House) discusses her previous marriage with a comedian, how a death in the family affected her dating life, and g...

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Why Won
Wes from Nailed It is here! (w/ Weston Bahr) from 2018-08-24T04:00

Weston Bahr is on the podcast to discuss what it's like to be harassed by Nicole on Nailed It, creepy DMs he gets from fans, all the dick jokes they've had to cut from the show, and so much more in...

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Why Won
Why'd You Stop Dating Me? (w/ Nick Snow) from 2018-08-17T07:00

Nicole and Nick Snow dated for a month, before Nick decided they should stop seeing one another. Now he's on the podcast to reminisce their first date, get closure on some things, and get confronte...

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Why Won
Nicole Answers a Dating Questionnaire (w/ Ego Nwodim) from 2018-08-10T04:00

Ego Nwodim joins Nicole to talk therapy and the times they've shat their pants. Ego takes a look at Nicole's updated Tinder profile. Nicole re-reads her Bagel Meets Coffee questionnaire and realize...

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Why Won
Shoplifting Stories (w/ Sabrina Jalees) from 2018-07-27T04:00

Sabrina Jalees (Netflix's The Comedy Lineup) joins Nicole to discuss hot celebrities they've taped to their bedroom walls, why they both enjoy gay porn, and both share their shoplifting stories. Listen

Why Won
Nicole's Opening Bumble Messages (w/ Fran Gillespie) from 2018-07-20T04:00

Fran Gillespie (SNL, Love, The Good Place) joins Nicole to discuss why it's harder for women to openly discuss sex than men. Nicole describes her Raya application process and shares her latest unsu...

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Why Won
Nicole's Latest Tinder Failures (w/ John Mason & Nicholas Stavola) from 2018-07-13T04:00

Nicole's oldest, best friends John Mason & Nicholas Stavola reminisce about their old high school romances, why John wouldn't take Nicole to their prom, and Nicole shares some hot pussy facts.
...

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Why Won
Love, Marriage, and Taxes (w/ Nick Wiger) from 2018-06-29T16:35:38

Nick Wiger (Doughboys, I Love You America) is on the show to gush about the love for his wife, learn about Nicole's green card marriage, and talk about responses they get from horny Doughboy fans. ...

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Why Won
Why Won't You Bake with Me (w/ Carl Tart) from 2018-06-22T05:00

Carl Tart (Comedy Bang Bang, Party Over Here) joins Nicole to discuss their favorite memes, the crazy foods Nicole's been subjected to on Nailed It!, and why they like swearing in front of kids. Listen

Why Won
Dating Thick (w/ Jon Gabrus) from 2018-06-15T08:00

The incredible Jon Gabrus (Raised by TV, Action Boyz, High & Mighty podcast) joins Nicole to share the adorable story on meeting his wife, and how it lead him to make out with all of his friends in...

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Why Won
Getting Paid for Sex (w/ Meatball and Big Dipper) from 2018-05-25T10:00

Buckle up, this episode is a wild one. Nicole is joined by drag queen Meatball and rapper Big Dipper! They discuss how they like to be choked in bed and the times they've gotten paid and have paid ...

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Why Won
Live from RuPaul's DragCon 2018 (w/ Eureka O'Hara) from 2018-05-18T10:00

It's Why Won't You Date Me's first live podcast! Eureka O'Hara (RuPaul's Drag Race season 9 & 10) joins Nicole to discuss what it's like to have sex in drag, how Drag Race prevents their contestant...

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Why Won
The World is Pretty Unfair (w/ Jake Weisman) from 2018-05-11T17:25:09

Jake Weisman (Corporate) joins Nicole to talk the traumatic incident that couldn't let him cum for a decade, his experience with Raya, and how he likes to slips into a his Robin Williams character ...

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Why Won
Lying About Your Age Online (w/ Molly Tarlov) from 2018-04-27T11:30

Molly Tarlov (MTV's Awkward) joins Nicole to talk about their one night stands, Nicole's experiences on a Jewish dating app, and lying about your age online.

You can play along and see Nic...

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Why Won
Body Positivity (w/ Tess Holliday) from 2018-04-20T11:55

Tess Holliday is a plus sized model who's attracted some creepy Instagram DMs. She's on the show to discuss body positivity, Nicole's latest Tinder failures, and the troubles of Skype sex.

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Why Won
Masturbating to Food (w/ Marcy Jarreau) from 2018-04-13T04:10

Nicole's good friend Marcy Jarreau (UCB Comedy, Loosely Exactly Nicole, Kar Dishin' Itpodcast) is on the show to discuss Nicole's hate for the Coffee Meets Bagel dating app, and soup.

Chec...

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Why Won
The Fappening (w/ Dan Black) from 2018-03-29T17:07

What if shit actually tasted great, and that's why people eat ass? Dan Black (UCB Comedy, TheComedians of Wrestling Podcast) is on the show to ask the real questions. Nicole introduces Dan to butt-...

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Why Won
Gay Bar Sidewalk Sale (w/ Mano Agapion) from 2018-03-23T04:10

Mano Agapion (UCB,Horny for Horror) joins Nicole to have a great discussion on race and gender identity, body dysmorphia, and a crazy Grindr threesome story.

Be sure to rate Why Won't You ...

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Why Won
What a Time to be Alive (w/ Langan Kingsley) from 2018-03-16T04:21

Langan Kingsley (Corporate) joins Nicole to discuss masturbating in public, stalking exes on Instagram, and what Nicole really wants in a man.

You can play along and see Nicole's Tinder bi...

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Why Won
Sexting (w/ Jen D'Angelo) from 2018-02-23T11:18:23

Jen D'Angelo (Workaholics, *Loosely Exactly Nicole) is on the show to discuss terrible prank shows they've filmed, why Nicole hates Christmas, and sexting.

You can play along and see Nicol...

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Why Won
Getting Drunk at the Movies (w/ Brooks Wheelan) from 2018-02-16T05:20

Brooks Wheelan (SNL) is on the show to discuss the ultra-exclusive Raya app, how he once got scabies from a girl he met in a liquor store parking lot, and the time he embarrassed himself in front o...

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Why Won
Growing Up Fat (w/ Jacob Wysocki) from 2018-01-26T05:00

Jacob Wysocki (*Loosely Exactly Nicole, UCB Comedy) joins Nicole to discuss being fat, going through puberty, and dating "normies".

You can play along and see Nicole's Tinder bio and photo...

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Why Won
Do Men Not Respond to Funny Women? (w/ Joanna Bradley) from 2018-01-19T05:00

Joanna Bradley (UCBComedy, Saturday Night Live) joins Nicole to share some of their bad Craigslist hookups stories, discuss the challenges of dating as a female comedian, AND reveal the time they h...

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Why Won
Would You Date a Chucklefucker? (w/ George Kareman) from 2018-01-12T05:00

George Kareman (UCB Comedy, Long Haired Businessmen) is on the show to teach Nicole how to use Hinge, and if they would ever date a chucklefucker. Nicole reveals her whole sneaky plan to make out w...

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Why Won
What's Up with Hair Conditioner? (w/ Ben Axelrad) from 2017-12-29T05:00

Nicole's friend Ben Axelrad (UCB Comedy, Definitely Dying Podcast) joins her to talk therapy, horrible dating stories, and why Nicole and Ben stopped dating after 3 dates.

You can play alo...

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Why Won
The Science Behind Dating Apps (w/ Emily Heller) from 2017-12-21T23:41

Emily Heller (Comedian, Baby Geniuses) joins Nicole to discuss the stats behind dating apps, steamy movies and the most boring man Nicole has ever dated.

Know how IMDB's star meter works? ...

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Why Won
Nicole's Pussy Pic That Went Too Far (w/ Sasheer Zamata) from 2017-12-15T05:00

Nicole's dear friend Sasheer Zamata (SNL) joins her to rate her Tinder bio, perform a live-reading of her Tinder conversations and Nicole shares the time the pussy pic she sent to a guy was deemed ...

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Why Won
Why Won't You Date Me? Here's a Little Tease. from 2017-11-15T20:08:44

Why is Nicole so single? She's cute, funny, has a fat ass, and loves giving blow jobs. This podcast is a quest to find the answer. Join Nicole and her guests - comedians and ex-lovers, as they boil...

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Why Won
Why Won't You Date Me? Here's a Little Tease. from 2017-11-15T20:08:44

Why is Nicole so single? She's cute, funny, has a fat ass, and loves giving blow jobs. This podcast is a quest to find the answer. Join Nicole and her guests - comedians and ex-lovers, as they b...

Listen
Why Won
Why Won't You Date Me? Here's a Little Tease. from 2017-11-15T20:08:44

Why is Nicole so single? She's cute, funny, has a fat ass, and loves giving blow jobs. This podcast is a quest to find the answer. Join Nicole and her guests - comedians and ex-lovers, as they b...

Listen
Why Won
Why Won't You Date Me? Here's a Little Tease. from 2017-11-15T20:08:44

Why is Nicole so single? She's cute, funny, has a fat ass, and loves giving blow jobs. This podcast is a quest to find the answer. Join Nicole and her guests - comedians and ex-lovers, as they b...

Listen