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

Drag queen mother Sasha Colby (winner of RuPaul's Drag Race S15) sits down with Nicole to discuss the unique challenges... more

Comedian Lisa Gilroy doesn't want you to think about her little tiddies, okay? So she shares her adventures in surprise... more

Comedy icon Kathy Griffin sits down with Nicole to tackle the burning question: Is she still cancelled? She discusses her... more

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

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

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

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

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

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

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

Sexologist and intimacy expert Shan Boodram (Sexology, Lovers & Friends) joins Nicole to teach her how to radiate better vibes... more

Is it worse to break up with someone, or get broken up with? Comedian Eric Andre (Bombing with Eric Andre)... more

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

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

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

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

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

It's episode 300! But how is Nicole STILL SINGLE?  On this milestone occasion, she's joined by her best friend Sasheer... more

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

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

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

Drag queen Robin Fierce (Drag Race S15) LIP-SYNCS TO THIS VERY PODCAST! She talks about remixing Nicole's comedy in her... more

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

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

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

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

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

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

Comedian Sam Taggart (host of StraightioLab) is here to spill some juicy insights on gay relationships and why they often... more

Twin drag queen icons Sugar & Spice (RuPaul's Drag Race S15) join Nicole for a conversation about why you can't... more

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

Actress Holly Robinson Peete (21 Jump Street, Queen's Court) opens up about her experience being in a relationship with someone... more

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

Comedian Ashley Gavin (host of We're Having Gay Sex) teaches Nicole all about lesbian sex and relationships. They cover scissoring... more

Actress/writer/director Zoe Lister-Jones (Slip) shares her experience opening and closing her "don't ask don't tell" poly relationship, what she's learned... more

Actor James Marsden (Sonic The Hedgehog, Hairspray, Jury Duty) joins Nicole to talk about his new singledom, remaining friends with... more

Drag queen icon Sasha Velour (winner of Drag Race S9) chats with Nicole about coming out to their dad at... more

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

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

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

Writer Bridger Winegar (host of I Said No Gifts!)  joins Nicole to discuss his experience being closeted to himself until... more

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

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

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

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

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

In January, Nicole shocked the world with an Instagram post announcing her relationship with comedian Dan Black. On this episode,... more

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

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

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

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