Love and dating can be messy—so let’s talk about it! On this multi-award-winning podcast, comedian Nicole Byer explores romantic highs, lows, and all the juicy stuff in between, alongside comedians, experts, and sometimes an ex or two. New episodes every Friday!
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Drag icon Mistress Isabelle Brooks (Drag Race S15, All Stars 10) returns, and she isn’t afraid to cause a little mayhem. She sits down with Nicole to talk about how she broke the rules of her All Stars season, and how her Drag Race sisters almost blew her cover. Mistress comes out as bisexual, explains her twink rebirth at 28, and shares how losing nearly 200 pounds in a year cost her a few relationships. Plus, the new legal name she’s picking out, organizing a Last Supper before her surgery, and why straight audiences can’t get enough of her cheerleader alter ego, Eleanor Charles. Nicole reveals which Drag Race queens she’d sleep with.
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If you caught your partner sexting an AI, would you break up with them? 1 in 7 people in committed relationships have a secret AI partner on the side. Tech journalist Bridget Todd (host of There Are No Girls on the Internet) shares her reporting on why so many people are falling in love with chatbots. She breaks down why AI chatbots are built to pull you into an intimate place, how dating apps are already using AI on you without you knowing, and why tech companies are betting on you being lonely and horny. Plus: the wildest AI love story she's come across, how to actually use AI to improve your dating life without crossing a line, and an optimistic look on AI and human connection.
Support this podcast by checking out our sponsors:
» JIYU Skin: The Korean skincare brand everyone is talking about. Our listeners get 20% off their entire order by using code DATEME at #JIYU #ad
Date with a Dominatrix (w/ Adam Conover)
Episode 464
Friday, October 23, 2026 • Duration 01:13:51
Three weeks after ending a 15-year relationship, comedian Adam Conover (Adam Ruins Everything, Factually!) went on a date with a 6'3" dominatrix whose first question was how he wanted to be dominated. He joins Nicole to share his side of the breakup with Lisa Hanawalt and dive into his newly single life, including exploring his sexuality, rediscovering himself, and experimenting with power dynamics in the bedroom. Plus, he shares stories from the messy dates he’s been on along the way, explains why he thinks straight men are the most sexually repressed people in America, and reveals how he’s learned to turn a bad date into a great night.
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I Wanna Be a Slut (w/ Lisa Hanawalt)
Episode 463
Friday, October 16, 2026 • Duration 42:02
Illustrator and friend Lisa Hanawalt (Bojack Horseman, Tuca & Bertie) returns to the podcast to chat about starting fresh in the dating scene after a 15-year relationship with Adam Conover, and what happened when they tried opening things up before they parted ways. Lisa explains wanting to be a slut while still needing to feel safe, her dates with a pathological liar who claimed he’d survived three train crashes, and what it’s like explaining PMDD mood swings to a new partner.
Next week, Adam Conover joins Nicole to share his side of things.
Lisa Hanawalt's new book, I Can’t Stop Thinking About Horses and Sex, is out October 20.
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Are YOU The Problem? (w/ Darlene Mitchell)
Episode 462
Friday, October 9, 2026 • Duration 01:03:50
Drag queen Darlene Mitchell(Drag Race S18) joins Nicole for a chat about finding love in the Instagram DMs, pulling off a tear-jerking surprise proposal, and coming out to her conservative family via a massive group text right before leaving to film reality TV. Darlene spills on a disastrous first date with an aspiring news anchor who was stuck in his persona, and dumping a college crush after finding out he was making out with someone ugly. Plus, they discuss why weaponized therapy speak on social media is ruining modern dating, and why you actually might need to change who you are for a partner if your habits are the problem. Finally, Nicole brings in her tooth to show off the instrument left in it by TruGlo Modern Dental. Avoid them at all cost!
» : Our listeners can buy one pair of glasses and get 20% off any additional pairs at — and using our link helps support the show. #WarbyParker #ad
Grilling Nicole's Man (w/ Ms. Pat)
Episode 461
Friday, October 2, 2026 • Duration 45:18
Comedian Ms. Pat joins Nicole to reveal the true secret to surviving a 33-year marriage, shares the brutal realities of menopause nobody talks about, and interrogates Nicole and the nice man in her life about why they aren't married yet. Plus, they dive into why a casual courthouse wedding beats a pricey party, the difference between taking care of people and being taken advantage of, and learning to finally advocate for yourself in relationships.
We’ve all heard the persistent dating mandate that the ideal man needs to be over 6ft tall. But what happens when you’re a 6"2 woman facing a dating pool of tall men who have coasted by on their height alone? According to comedian Marcella Arguello, it's time to abandon the tall man propaganda - and finally give short kings the respect they deserve. Marcella returns to the podcast to break down the brutal body standards we face in the dating pool. Nicole and Marcella also discuss the tragedy of having big dicks attached to bad people, and debate whether lying can actually keep the peace in a relationship. Plus, the story how she got a boyfriend by playing the long game.
Support this podcast by checking out our sponsors:
» JIYU: The Korean skincare brand everyone is talking about. Our listeners get 20% off their entire order by using code DATEME at https://www.jiyuskin.com/dateme
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Finally Ready to Confess (w/ BenDeLaCreme)
Episode 459
Friday, September 18, 2026 • Duration 50:05
Drag queen icon BenDeLaCreme (Drag Race 6, All-Stars 3) joins Nicole to spill some major breaking news: they've been secretly separated from her partner of 8 years. They talk about the effort it takes to try to stay friends with an ex, the confusing reality of jumping back into the LA dating pool in your mid-40s, and why it's impossible to tell if a guy wants to date you or just wants exclusive Drag Race gossip. Plus, DeLa breaks down her brilliant move to self-eliminate on All-Stars 3, and Nicole reveals the unhinged manifestation trick she used to lock down the nice man in her life.
See The Jinkx and DeLa Holiday Show on tour in a city near you! Get tickets and buy the upcoming book at https://www.jinkxanddela.com.
» Hinge: Try Hinge’s new feature, Friend’s Take. Send your link to the group chat and let the people who know you best do the talking.
The Most Chaotic Friendship Ever (w/ Meatball and Big Dipper)
Episode 458
Friday, September 11, 2026 • Duration 01:14:54
Why Won't You Date Me is taking a quick break this week while Nicole is out of town filming, but we'd never leave you high and dry! Instead, Nicole is sharing one of her all-time favorite episodes of her other podcast, Best Friends. Best Friends Nicole and Sasheer are joined by two very special guests and hosts of the podcast Sloppy Seconds, Big Dipper and Meatball! Consider this a wild masterclass in relationships and how hard it is to maintain a bond with someone, featuring wild stories about naked meetings at gay resorts, eating ribs nude in bed, and bombing TV auditions in a speedo. Normal WWYDM programming resumes next week!
Support this podcast by checking out our sponsors:
» Warby Parker: Our listeners can buy one pair of glasses and get 20% off any additional pairs at https://WarbyParker.com/DATEME — and using our link helps support the show. #WarbyParker #ad
The AI Dating Dystopia (w/ Jarvis Johnson)
Episode 457
Friday, September 4, 2026 • Duration 51:43
YouTuber Jarvis Johnson (Host of Sad Boyz) joins Nicole to discuss the dystopian reality of how AI has changed the dating landscape, from people now dating their AI and the trend of men using ChatGPT to automatically swipe and chat with women for them. Jarvis opens up about his regret about having a public relationship and why he now chooses to keep his life private after a very public internet breakup. They also discuss how neurodivergence impacts relationships, why undiagnosed ADHD can hold someone back, Rejection Sensitive Dysphoria (RSD), medication they are taking, and how Nicole is managing her PMDD.
Support this podcast by checking out our sponsors:
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» Wayfair:Transform your space with pieces that hold up to real life. Join Wayfair Rewards today to get 5% back on every purchase. Head to https://Wayfair.com or shop the Wayfair app for all things home.
» Cash App: Download Cash App Today: https://capl.onelink.me/vFut/3v6r90n6 #CashAppPod Cash App is a financial services platform, not a bank. Banking services provided by Cash App’s bank partner(s). Prepaid debit cards issued by Sutton Bank, Member FDIC. Cash App Visa® Debit Flex Cards issued by Sutton Bank, Member FDIC, and The Bancorp Bank, N.A., pursuant to a license from Visa U.S.A. Inc. See terms and conditions for the Sutton prepaid card, Sutton debit flex card, and Bancorp debit flex card. Discounts and promotions provided by Cash App, a Block, Inc. brand. Visit cash.app/legal/podcast for full disclosures.
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