Why Won't You Date Me? with Nicole Byer

Updated: 01 Aug 2025 • 409 episodes
headgum.com/why-wont-you-date-me

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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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

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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 Bes

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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 ta

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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

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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

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04 Jul 2025 • EN

We Dated?! (w/ Lou Wilson)

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 minute

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