Boo! Friend and comedian Mano Agapion ( Drag Her , We Love Trash ) joins Nicole for a Halloween special with a creepy ghost story, a "psychic" sex criminal, funeral planning, and lipstick teeth. Mano recounts the chilling time he saw a ghost in Greece, the so-called astrologer who stuck a finger up his bum, and Nicole shares her plan for a funeral birthday where friends give eulogies while she lies in a casket. Plus, Nicole realizes she's too clingy in her relationship. it’s our most haunted epi...
Oct 31, 2025•1 hr 8 min•Ep. 413
Drag queen icon Kim Chi ( RuPaul's Drag Race S8 , author of Kim Chi Eats The World ) joins Nicole to talk about what it’s like to have never dated anyone, and whether she even wants to. She opens up about being afraid to get hurt, growing up with crushes who didn’t like her back, and why are all the conspiracy nuts booed up? Kim shares wild stories from her drag-tour days (including the time she was recognized during a lap dance), having a twink convention show up at her hotel, and story about q...
Oct 24, 2025•49 min•Ep. 412
Model and Drag Race pit crew member Bruno Alcantara joins Nicole to discuss his love for biting (and the time he got kicked out of a bar for it), being barefoot on set of Drag Race, working as a massage therapist and life coach, and discovering he was gay after having a couple of girlfriends. Plus, Bruno gives Nicole a happy ending massage while sharing his best advice as a life coach. Check out Happy Endings with Bruno on WOW Presents Plus. Watch this episode on our YouTube channel at https://w...
Oct 17, 2025•50 min•Ep. 411
Drag queen Angeria Paris VanMichaels (Winner of RuPaul's Drag Race All Stars S9) wants your hole pic. She joins Nicole to talk about the etiquette of hooking up with a RuGirl, those confusing “boyfriend things” that blur situationships, and why being the one who always texts first is exhausting. Angeria opens up about what she really wants in a partner, how she’s manifesting real love after years of being single, and the thrill of the chase. Plus, Nicole receives a sandwich in her email. Watch t...
Oct 10, 2025•1 hr•Ep. 410
Nurse practitioner and pole dancer Neda Momeni is here and teaches Nicole a lot! From her years as a labor and delivery nurse, she explains what actually happens in the hospital during childbirth and what most people never hear about until they’re living it. She talks about Muslim dating, from family expectations to apps like Minder and her experience using an online matchmaker. Pressure pushed her to marry the wrong man, and she ended up going no-contact with her parents. After cutting ties, po...
Oct 03, 2025•1 hr 3 min•Ep. 409
Drag queen, singer, and actress Adore Delano ( RuPaul's Drag Race S6, All Stars 2 , American Idol ) joins Nicole to share stories about hooking up with go-go dancers, filming a sex tape she regrets, and her path to sobriety. She opens up about transitioning twice, the facial feminization surgery she underwent, and her current relationship with a trans man Nicole and Adore swap dating lessons, talk about why a healthy relationship can feel so strange, and discuss why an amusement park date is the...
Sep 26, 2025•1 hr 1 min•Ep. 408
Actress Rachel Bilson ( The O.C. , Broad Ideas ) once lost a job over something she said on a podcast. She tells Nicole what that was like, current cancel culture, and why “free speech” doesn’t always apply to everyone. Rachel shares some of her wildest dating stories, from terrible first dates, rejected kisses, and men who love bomb too fast. Also, is it good to call before a first date, or is it unhinged? Rachel discusses what it's like to date in the spotlight, the time she got into a fight w...
Sep 19, 2025•47 min•Ep. 407
Rapper and friend Big Dipper (host of Sloppy Seconds ) returns to the pod! He and Nicole dive into how he became a bear, the many “gaybels” that shape queer dating culture, and the highs and lows of Bear Week and pig events, from the wild parties to the moments that left him questioning everything. Dipper unpacks the twink vs. bear dynamic and explains compersion - the joy of watching your partner get pleasure from someone else. He also shares the wild story of a influencer showing up to his sex...
Sep 12, 2025•1 hr 12 min•Ep. 406
Comedian, clown, and artist Jenson Titus ( of @VeryGayPaint ) tells Nicole what it was like to date someone who's in the process of transitioning. The experience made him realize he’s bi, and left him feeling “more queer” than ever. He talks about the challenges of having a "Very Gay" brand while dating a woman, launching his mural business, and the surreal job of painting RuPaul’s 1-bedroom, 5-closet mansion. They talk about their dream date ideas, the act of clowning, and Nicole shares her pla...
Sep 05, 2025•49 min•Ep. 405
Olympic figure skater Adam Rippon (Winner of Dancing with the Stars ) joins Nicole to share the dating life of a Olympian. He shares what it was like being one of the first openly gay U.S. Olympians, why the infamous Olympic condoms left him disappointed, and what the sex life in the Olympic Village is really like. He also breaks down for Nicole exactly what it takes to become an Olympian, and the incestuous nature of figure skaters. Meanwhile, Nicole and her boyfriend take a vacation where he g...
Aug 29, 2025•56 min•Ep. 404
Co-writers Dan Gregor and Doug Mand ( The Naked Gun ) have been writing partners for twenty years - which is basically a marriage at this point. They tell Nicole about the time they were "dumped" by Adam Pally, how they’ve kept a friendship and business alive without burning each other out, and the rabbi who completely ruined a wedding by trying to do bits. They also shared the best marriage advice they’ve ever gotten, and what it feels like to spiral when you don’t think you’re worthy of love. ...
Aug 22, 2025•1 hr 4 min•Ep. 403
For Roz Hernandez , dating as a sober, trans woman comedian is a trifecta of difficulty - and finding love hasn’t been easy. She tells Nicole about going to 4 different Etsy psychics to sketch her future husband, using Grindr to find dates willing to explore haunted places, and the hookup stories that came from visiting 45 gay bars across the country. She opens up about the surprising ways gay men have treated her, why she’s stopped dating straight men altogether, and the many times she’s been g...
Aug 15, 2025•1 hr 8 min•Ep. 402
International award-winning burlesque dancer Jessabelle Thunder joins Nicole to talk about why so many partners say they’re cool with burlesque - until they’re not. She shares how she transformed from a shy girl into a commanding headliner, the different styles of burlesque dancing, and the time she broke her ankle on stage mid-show. Jessabelle also relives a London date with an Irish DJ who argued he should be allowed to say the N-word. Plus, Nicole forgets her meds, spirals on the future of AI...
Aug 08, 2025•1 hr 1 min•Ep. 401
Before she was an activist, Monica Lewinsky was the most publicly shamed woman in America. Now, she's reclaiming her story, and her dating life. For the 400th episode of Why Won’t You Date Me? , Monica joins Nicole to talk about dating after a major scandal, being labeled “unmatchable” on eHarmony, and learning to enjoy life when pop culture won’t stop referencing you. She reflects on hosting the wild early-2000s reality show Mr. Personality , shares the worst dates she’s ever had (including one...
Aug 01, 2025•56 min•Ep. 400
Exciting news from Nicole: Best Friends is BACK and 1) now on Headgum, 2) with FULL VIDEO EPISODES! Enter the pantheon of best friendship and check out Nicole and Sasheer's first episode back, available now on Apple Podcasts , Spotify , or wherever you get your podcasts. New episodes every Wednesday. Subscribe to the Best Friends YouTube channel https://youtube.com/@NicoleandSasheer for video episodes. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19...
Jul 30, 2025•33 sec
Comedian Devon Walker (SNL) joins Nicole to tell the story of how he met his girlfriend on a live blind date podcast. He figured it was just a bit - until the audience voted for them to win an Applebee’s gift card and that turned into their actual first date. 3 years later, they’re still together! He and Nicole also talk about the woman who went viral eating 48 oysters on a first date , why it’s a red flag if your partner suddenly starts doing open mics, and how it feels when people send you uns...
Jul 25, 2025•58 min•Ep. 399
Comedian and friend Josh Sharp ( Dicks: The Musical ) returns to the podcast! Nicole and Josh kick things off by reminiscing about the chaotic live show where Nicole interviewed a man in the audience she had slept with. From there, they get into Josh’s foolproof flirting strategy at the club, Annabelle the haunted doll’s cursed tour across America, attending a Big Dick contest, and Josh’s near-death experience in Puerto Vallarta that left him facedown in the ocean with no memory of his own name....
Jul 18, 2025•56 min•Ep. 398
Drag queen icon Meatball is back! She and Nicole get into it all - being in her top era, loving the single life, and having weekend boyfriends in different cities. But also... why dating is still so hard when you do drag. Meatball opens up about losing guys the second they find out she’s a queen, and how frustrating it is watching her roster shrink because of it. And of course, the wild date stories are endless - projectile vomiting in a car on a date, sucking 3 different dicks in one night (one...
Jul 11, 2025•1 hr 4 min•Ep. 397
Happy 4th of July!(?) Comedian Lou Wilson ( Dimension 20, Jimmy Kimmel Live!) joins Nicole to reflect on the wild state of America. He shares his terrible time living in Boston, where white guys frequently asked him for the N-word pass. They talk about what it was like to sell out Madison Square Garden in just 10 minutes with Dimension 20 , being a “silly billy” on dates, and the moment Lou realized bits don’t always land on dates when you’re trying to build intimacy. They also bond over the gui...
Jul 04, 2025•51 min•Ep. 396
Actress Jessica Lowe ( The Righteous Gemstones, Minx , Wrecked ) joins Nicole to share the romantic saga of falling in love on a Second City cruise ship. On the ship, she met a British bassist who became her cruise ship boyfriend - whom she later realized wasn’t as smart as she thought his accent sounded (he tried to dry his pants on a ceiling fan and designed a nightmare demon tattoo for himself). Jessica recalls dating a Dutch chef with a penis that was “too much!” and recounts what might be t...
Jun 27, 2025•52 min•Ep. 395
TV writer Lauren Ashley Smith ( A Black Lady Sketch Show , Smith Sisters Live ) joins Nicole to talk about how she met her wife the old-fashioned way - through Time Out New York ’s Singles issue. Lauren reveals the strange public response to being a “bachelor” in a magazine, how her wife was one of the only white women working at BET , and the complications that came with planning an interracial lesbian wedding. She also recalls a bizarre school Valentine’s Day test that matched students based o...
Jun 20, 2025•59 min•Ep. 394
Actor Michael Urie ( Shrinking, Ugly Betty ) joins Nicole to discuss the wild hookup culture at Julliard, and the love triangle he had that went sour. Once he got fame from Ugly Betty, he starts going on dates with people who only seem interested in the version of him they saw on TV, until a second shot with actor Ryan Spahn turns into a 17-year partnership. He tells the story of a friend who died singing Britney Spears at karaoke, and lists the surprisingly beautiful ways other pals have died. ...
Jun 13, 2025•59 min•Ep. 393
Comedian and friend Betsy Sodaro (Ghosts, A Funny Feeling ) joins Nicole to swap crazy Las Vegas stories, their experience getting slammed by puberty, and debate why we shouldn’t have to pay taxes right now (plus what happened when Nicole skipped paying taxes for 5 years). Betsy reveals what life was like spending six months in a hotel, and Nicole confesses she nearly launched an anime-recap podcast with an ex. Plus: the time a customer-service call at Lane Bryant turned into phone sex. WATCH th...
Jun 06, 2025•54 min•Ep. 392
Actress Edi Patterson ( The Righteous Gemstones ) joins Nicole to talk about falling in love with her improv teacher, hiding their relationship from the world, and mistaking his proposal for a joke. She opens up about being a late bloomer in dating, throwing house parties that felt straight out of a '90s film, and the one dating lesson she learned from a kid that she wishes everyone would follow. Plus: ghosting guilt, cringey first date stories, 90 Day: Hunt for Love , and the time Nicole’s dog ...
May 30, 2025•50 min•Ep. 391
Actress Rose McIver ( Ghosts , iZombie , voice of Headgum) joins Nicole to explain New Zealand, why she doesn’t post her loved ones on social media, and talk about all the cute, funny other ways people show love. They get into weird animal relationship stories, like the woman in love with a dolphin (who died of heartbreak), the man who tried to live among grizzlies, and Nicole’s dream of becoming queen of the whales. Plus: a simple dinner hosting hack from Meghan Markle. WATCH this episode here:...
May 23, 2025•54 min•Ep. 390
Bob the Drag Queen ( The Traitors , winner of RuPaul's Drag Race S8 ) returns to the podcast to derail the show. This time, Bob interviews Nicole about her current relationship, run through their plans to prep for tariffs, and discuss LA's newest serial killer. He sniffs out the ulta-rich cast members on The Traitors, shares what he hates about Italy, and Canada’s ex-prime minister's blackface scandal. Plus, Nicole shares her latest showdown with the cops. Buy Bob's new book, Harriet Tubman: Liv...
May 16, 2025•1 hr 8 min•Ep. 389
TikTok star Drew Afualo joins Nicole to share her enemies‑to‑lovers love story and the worst dates that taught her to trust her gut. She tells the time she dated a man who drank ocean water and ended up getting his stomach pumped, walks through her viral list of red flags in men, and the backlash she received online for sharing it. They dig into the male loneliness epidemic, red‑pill culture, and what we can learn from the dating on Love On The Spectrum . Plus, Nicole tells the time she accident...
May 09, 2025•1 hr 6 min•Ep. 388
Comedian and Nicole's fictional boyfriend Colton Dunn ( Superstore, Grand Crew, Key and Peele ) joins Nicole to talk about dating customs in Europe (and what we can learn from them), getting mad at your partner over what they did in your dream, and what surprised him most about becoming a dad. He reflects on why improv might never be cool- even if you're good at it, and shares behind-the-scenes stories from some of the most iconic Key & Peele sketches. Plus: diaper blowouts, fake babies at D...
May 02, 2025•58 min•Ep. 387
Comedian Owen Burke ( Drunk History ) joins Nicole for a conversation recorded in the middle of the Los Angeles fires (things were unhinged). They talk about trying to function while the world is burning, the early days of UCB, and how Owen managed to find a wife while being painfully shy and awkward with dating—and how you can too. Plus, Nicole shares the time she gave John Mulaney her number. John, please call. Watch this episode here: https://youtu.be/_TODPIkV8nY Write Nicole a dirty message!...
Apr 25, 2025•1 hr 5 min•Ep. 386
Comedian and friend Jackie Johnson was terrified to do this podcast… until she got a divorce. She joins Nicole to talk about dating a record number of canceled UCB comedians, surviving a nightmare marriage, and only realizing she was unhappy after it ended (plus how to spot signs of abuse in your own relationship). Jackie shares how therapy—and a witch’s spell—helped her find true love. Plus, they discuss the red flags they missed in past relationships, why getting married on Valentine’s Day was...
Apr 18, 2025•1 hr 8 min•Ep. 385
