Comedian Nick Kroll (Big Mouth, Oh, Hello) joins Nicole for an episode of just... absolute chaos. They discuss how Nick... more

Comedian Sherry Cola (Joy Ride, Turning Red) shares her journey of coming out as bisexual, how she met her girlfriend,... more

Comedian Sarah Silverman sits down with Nicole to discuss meeting her boyfriend over Call of Duty, the challenges of dating... more

We're back - and now in video form! Comedian and actress Lauren Lapkus (Newcomers podcast) joins Nicole to discuss why... more

In this best of episode, Emmy-award winning actress Keke Palmer (Nope, Lightyear) shares with Nicole how she got her first kiss from MySpace,... more

While we're on hiatus, we're bringing you the best of the podcast – completely ad-free! In this episode, Nicole’s close... more

In this iconic episode, Gabrus (High & Mighty), Nick Wiger and Mike Mitchell (Doughboys) join Nicole fresh off a power-hour... more

While we're on hiatus, we're revisiting one of Nicole's favorite episodes! Comedian and actor Paul Scheer (The League, Black Monday) joins Nicole to... more

We’re bringing you the best of Why Won’t You Date Me?—completely ad-free! In this episode, Nicole is joined by Skyler,... more

As we continue our hiatus, we're bringing back some of Nicole's all-time favorite episodes! And oh boy, BUCKLE UP, because... more

Actress Jameela Jamil (The Good Place) joins Nicole to share her most horrifying booty call story. They dive into the... more

We’re taking a short hiatus, but don’t worry—we’ll be back soon with brand new episodes, including more video podcasts! In... more

Actress Garcelle Beauvais (The Real Housewives of Beverly Hills) joins Nicole to discuss dating the likes of Michael Jordan, Larry David,... more

Comedian Riki Lindhome (Garfunkel and Oates, AfrAId) joins Nicole to discuss her harrowing fertility journey, dating someone new just two... more

Comedian and actress Chloe Fineman (SNL) joins Nicole to discuss orgasmic meditation and the strange men behind the practice. She... more

Sophia Stallone (The Family Stallone) shares what it's like to date when your dad is Sylvester Stallone. Sophia recounts cringey dates... more

Comedian and "ho-fessional" Akeem Woods joins Nicole to share his crazy sexcapades. He tells the story about his first Pride... more

Comedian Ryan Beck (Girl Code) joins Nicole to discuss the worst places to be broken up with and debate when... more

Comedian Luenell (Borat, Hacks) joins Nicole to discuss the decision that led her to start an OnlyFans, dating a man... more

Actor/TikToker Boman Martinez-Reid (@Bomanizer) joins Nicole to discuss the pitfalls of launching your relationship on social media, witnessing his ex... more

Lala Kent (Vanderpump Rules) joins Nicole to reveal why she chose a sperm donor for her pregnancy and explain the... more

Actress Poppy Liu (Hacks) joins Nicole to discuss how she accidentally dated a cult leader, her exhausting year as a dominatrix... more

Comedian Clark Jones joins Nicole to discuss a wild hookup after a drug-fueled comedy show, the experience that turned him... more

Comedian Keith Robinson has faced two strokes that have affected half his mobility and speech. He shares with Nicole how... more

Actor Tony Hale (Veep, Arrested Development, Inside Out 2) joins Nicole to discuss how he accidentally themed his marriage proposal... more

Comedian David Gborie (voice of Comedy Central, All Fantasy Everything, My Momma Told Me) joins Nicole to discuss the hottest... more

Relationship therapist and star of 90 Day Fiancé: Love in Paradise, Alex Roshon, is here to answer all of Nicole's... more

This season of MILF Manor takes a wild turn as MILFs date young men and their fathers at the same... more

Drag queen Mistress Isabelle Brooks (Finalist of RuPaul's Drag Race S15) joins Nicole to discuss her dating life as 'The... more

Actor Jesse Tyler Ferguson (Modern Family) joins Nicole to share his proposal story and how it was hilariously overshadowed by... more

Writer Jessica Gao (She Hulk: Attorney at Law, Rick & Morty) joins Nicole to discuss male friends who are "single... more

Kamie Crawford (Host of Catfish: The TV Show)  joins Nicole to explore the most bizarre catfishing schemes she's witnessed, and... more

Comedian Craig Conant joins Nicole to discuss how sleeping with a chucklefucker led to him to become a baby daddy,... more

WNBA superstar and Olympic gold medalist A'ja Wilson joins Nicole to discuss how her 6'4" height shapes her dating experiences,... more

Actor William Stanford Davis (Abbott Elementary) joins Nicole to share how he met his wife in an improv class, the unique... more

Comedian and writer Moshe Kasher chats with Nicole about being a ho, going to a 12-step program for sex addicts,... more

Comedian Franchesca Ramsey (iCarly) joins Nicole to discuss what she's learned after going through an expensive divorce, finding singles in the... more

Comedian Zach Woods (Silicon Valley, The Office, In The Know) joins Nicole to discuss shooting your shot with your crush, having... more

Comedian and writer Asha Ward (SNL) joins Nicole to share her wild roommate sex drama, reflects on being raised by a... more

Musician LU KALA joins Nicole to discuss why the dating world feels so broken after COVID, the skill behind a... more

Comedian Rory Scovel joins Nicole for a chat about their Valentine's Day experiences, dealing with horny audience members, his cute proposal... more

Comedian Lamar Woods (New Girl, Grand Crew) joins Nicole to discuss their 2024 vision boards, taking yourself on self care... more

Comedian Laurie Kilmartin (Conan) joins Nicole to discuss all things Valentine's Day - the gifts, their dream dates, and Nicole's... more

Comedian Rashida "SHEEDZ" Olayiwola (Jury Duty) joins Nicole to discuss the best places to go for singles mixers, the time... more

Comedian Stavros Halkias (Fat Rascal, Stavvy's World) joins Nicole to discuss hooking up with audience members, why he believes he... more

Comedian and writer Garrick Bernard (Rick & Morty, Solar Opposites) joins Nicole to discuss finding love at BuzzFeed, the awkwardness... more

Comedian and friend Mark Rennie (The Onion) joins Nicole to share his experience attending a gay meetup on a Star... more

Comedian Lisa Ann Walter (Abbott Elementary) joins Nicole to share her unique marital experiences, from a husband who eventually came... more

Comedian Liz Barlow discusses breaking up with a boyfriend who doxxed people, her challenging experience dating women, the story of... more

Comedian Katrina Davis joins Nicole to discuss holiday gift giving, the delicate process of home decorating when moving in with... more