Episodes

  • Tossing Shade (w/ Bosco)

    Tossing Shade (w/ Bosco)
    Jun 26 2026
    Drag queen icon Bosco (Drag Race S14, All Stars S10) makes her return to toss even more shade. She shares why the secret to polished drag is having mean friends, how to filter out dumb men in your dating life, and trades stories with Nicole about their most questionable fashion eras. They also discuss facial feminization surgery (and the boy queens getting it) and why we all need some more razzle dazzle in our lives. Plus, Nicole has become a human white noise machine for the nice man in her life.See Bosco on tour! Get tickets at dragfans.com. Buy 2 tickets, get the 3rd free. The whole polycule can come!Check out Bosco's new Magic The Gathering show, Spell Slayers on YouTube.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast by checking out our sponsors:• Warby Parker: Our listeners can buy one prescription pair and get 20% off any additional pairs at WarbyParker.com/DATEME — and using our link helps support the show. #WarbyParker #ad• Chime: Chime is not just smarter banking, it is the most rewarding way to bank. Join the millions who are already banking fee free today. Head to Chime.com/DATEME.• Squarespace: Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME.• Audible: Listen to Heads Will Roll: Heir Apparent, available now on Audible. Go to Audible.com/headswillrollseries to start listening today.Check out all of our sponsors and discount codes at wwydm.notion.site/sponsors.Follow:All Links: linktr.ee/whywontyoudatemeTour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerThis is a Headgum podcast. Advertise on Why Won't You Date Me? via Gumball.fm.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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    50 mins
  • Creatively Building a Family (w/ Sabrina Jalees)

    Creatively Building a Family (w/ Sabrina Jalees)
    Jun 19 2026
    Comedian Sabrina Jalees (Mating Season) returns to the podcast! Sabrina talks about how she and her wife made a family, including picking out a sperm donor and performing a home insemination using a dog catheter. They break down the recent news about websites hosting non-consensual "sleep content" and the terrible networks of men coaching each other on how to assault their partners. Sabrina shares her attempt at a magic trick proposal while her partner dealt with a bathroom emergency, and they discuss: Can 2 butches make a right? Plus, why we need to rethink how we speak about pregnancy loss, and Sabrina makes a strong case for freezing your eggs.Check out Mating Season on Netflix.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast by checking out our sponsors:• FirstLeaf: Get personalized wines, delivered. Head to TryFirstleaf.com/DATEME to sign up and you'll get 50% off your first box PLUS free shipping for an entire year• 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.Follow:All Links: linktr.ee/whywontyoudatemeTour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerThis is a Headgum podcast. Advertise on Why Won't You Date Me? via Gumball.fm.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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    59 mins
  • Having A Self-Love Affair (w/ Jujubee)

    Having A Self-Love Affair (w/ Jujubee)
    Jun 12 2026
    You ready for some good juju? This week, iconic drag queen Jujubee (Drag Race, Stop! That! Train!) joins Nicole to talk about the power of self-love and why she’s officially stopped looking for a relationship. Nicole pays tribute to her first dog, Charlie, and the two discuss why the true soulmates are actually the animals in our life. Jujubee shares her philosophy on why love never dies, and opens up about the clarity she's found from being 9 years sober. She shares her best advice on having the ultimate solo date, and the two Delta Diamond Divas share their travel tips.Go see Stop! That! Train! in theatres today. Check out Jujubee's latest EP, MESS FOR YOU.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast by checking out our sponsors:• Jones Road Beauty: Use code DATEME at jonesroadbeauty.com to get a Free Gift with your first purchase! #JonesRoadBeauty #ad• Warby Parker: Our listeners can buy one prescription pair and get 20% off any additional pairs at WarbyParker.com/DATEME — and using our link helps support the show. #WarbyParker #ad• Squarespace: Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME.• Wayfair: Patio season is here and these deals won’t last! Head to Wayfair.com right now to get your outdoor space ready for way less.Follow:All Links: linktr.ee/whywontyoudatemeTour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerThis is a Headgum podcast. Advertise on Why Won't You Date Me? via Gumball.fm.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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    48 mins
  • Setting Relationship Boundaries (w/ Trixie Mattel)

    Setting Relationship Boundaries (w/ Trixie Mattel)
    Jun 5 2026
    Drag queen Trixie Mattel (Drag Race S7, All Stars 3) returns to the podcast! After experiencing how exhausting it is to navigate a private breakup while smiling through a press tour, Trixie opens up about why she is now fiercely protective of her new relationship. Nicole explains why Drag Race S7 is her all-time favorite season, and the girls discuss wild dating reality TV shows like 90 Day Fiancé, Love After Lockup, and Love on the Spectrum, plus whether Trixie would ever actually compete on The Traitors. Trixie also discusses her impersonator recent retirement, gives her honest advice to all the gay singles out there, and reveals her obsession with crime scene cleanup.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastTake our listener survey and shape the future of the podcast!Support this podcast by checking out our sponsors:• Jones Road Beauty: Use code DATEME at jonesroadbeauty.com to get a Free Gift with your first purchase! #JonesRoadBeauty #ad• Betterhelp: This show is sponsored by BetterHelp. Visit betterhelp.com/dateme today to get 10% off your first month.• 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.Follow:All Links: linktr.ee/whywontyoudatemeTour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerThis is a Headgum podcast. Advertise on Why Won't You Date Me? via Gumball.fm.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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    1 hr and 15 mins
  • Measuring Love & Male Delusion (w/ Tracie Thoms)

    Measuring Love & Male Delusion (w/ Tracie Thoms)
    May 29 2026

    Tracie Thoms (RENT, The Devil Wears Prada 2) joins Nicole to discuss her 8-year journey to join the iconic cast of RENT, the wild logic men use to avoid commitment, and why some of them want all the benefits of a girlfriend with zero of the responsibility. Tracie also breaks down the nightmare of having dated someone who tried dictate her career, and reveals why living apart from her partner has actually been the ultimate relationship hack. Plus, why does true love make you feel sleepy? And Nicole opens up about her PMDD diagnosis.

    I'm just such a big fan of RENT and so happy we have Joanne on, omg folks this is a big one for me personally. Rentheads unite!


    Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcast


    Take our listener survey and shape the future of the podcast!


    Support this podcast by checking out our sponsor:

    • Squarespace: Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME.


    Follow:

    All Links: linktr.ee/whywontyoudateme

    Tour Dates: linktr.ee/nicolebyerwastaken

    YouTube: @WhyWontYouDateMePodcast

    TikTok: @whywontyoudatemepod

    Instagram: @nicolebyer

    X: @nicolebyer

    This is a Headgum podcast. Advertise on Why Won't You Date Me? via Gumball.fm.

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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    52 mins
  • Would You Date YOU? (w/ Relationship Therapist Esther Perel)

    Would You Date YOU? (w/ Relationship Therapist Esther Perel)
    May 22 2026

    World famous relationship therapist Esther Perel has been studying relationships for over 40 years. She joins Nicole to share the most common problems couples seek therapy for, the 3 types of conflicts we fight over, and how to productively resolve them. Esther discusses how to get over "icks" while dating, and challenges us to ask ourselves: what "icks" would people find in you? They also explore exactly why modern dating feels so incredibly tough right now, the fact that therapy speak has gone mainstream thanks to shows like The Sopranos, and whether that's a good or bad thing. Plus, Esther shares a wild story about her first therapy session between a man and his AI girlfriend, and she totally flips the script on Nicole to ask the ultimate question: Would you date you?


    Celebrate the 20th anniversary of her groundbreaking book, Mating in Captivity.


    Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcast


    Take our listener survey and shape the future of the podcast!


    Support this podcast by checking out our sponsor:

    • Chime: Chime is not just smarter banking, it is the most rewarding way to bank. Join the millions who are already banking fee free today. Head to Chime.com/DATEME.


    Follow:

    All Links: linktr.ee/whywontyoudateme

    Tour Dates: linktr.ee/nicolebyerwastaken

    YouTube: @WhyWontYouDateMePodcast

    TikTok: @whywontyoudatemepod

    Instagram: @nicolebyer

    X: @nicolebyer

    This is a Headgum podcast. Advertise on Why Won't You Date Me? via Gumball.fm.

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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    1 hr and 7 mins
  • Writing Heated Rivalry (w/ Rachel Reid)

    Writing Heated Rivalry (w/ Rachel Reid)
    May 15 2026

    Author Rachel Reid (Heated Rivalry) joins Nicole to chat about the wild, viral success of her steamy queer romance novels and the hit TV adaptation. She shares how she met her husband while performing a smelly, hockey-themed burlesque act, and the dynamic that keeps their 20-year one sided open marriage working for them. She discusses the creative process behind writing explicit romance between men, and exactly why she absolutely does not want to hear your glowing reviews of her work. Plus, Rachel opens up about navigating her recent Parkinson's diagnosis.


    Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcast


    Take our listener survey and shape the future of the podcast!


    Support this podcast by checking out our sponsors:

    • FirstLeaf: Get personalized wines, delivered. Head to TryFirstleaf.com/DATEME to sign up and you'll get 50% off your first box PLUS free shipping for an entire year

    • Wayfair: Get prepped for patio season for way less. Head to Wayfair.com right now to shop all things home. Wayfair. Every style. Every home.


    Follow:

    All Links: linktr.ee/whywontyoudateme

    Tour Dates: linktr.ee/nicolebyerwastaken

    YouTube: @WhyWontYouDateMePodcast

    TikTok: @whywontyoudatemepod

    Instagram: @nicolebyer

    X: @nicolebyer

    This is a Headgum podcast. Advertise on Why Won't You Date Me? via Gumball.fm.

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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    47 mins
  • Farting All Night on a First Date (w/ Beck Bennett)

    Farting All Night on a First Date (w/ Beck Bennett)
    May 8 2026
    Comedian and actor Beck Bennett (SNL, What's Our Podcast?) joins Nicole to talk about meeting his wife on a sketch shoot and how his wallet-less first date turned into a romantic, fart-filled sleepover. Beck opens up about surviving long-distance dating while shooting SNL, why he believes "love is trust," and the Joshua Tree engagement trip that ended with them sleeping in separate twin beds. He shares the creative ways he jerked off as a kid (including using a Sock'em Bopper and a vibrating pen), and Nicole admits to stealing her first vibrator from Spencer’s Gifts.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastTake our listener survey and shape the future of the podcast!Support this podcast and get discounts by checking out our sponsors:• Jones Road Beauty: Use code DATEME at jonesroadbeauty.com to get a Free Gift with your first purchase! #JonesRoadBeauty #ad • Warby Parker: My listeners can buy one prescription pair and get 20% off additional pairs at WarbyParker.com/DATEME — and using our link helps support the show. #WarbyParker #ad• Squarespace: Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME.Follow:All Links: linktr.ee/whywontyoudatemeTour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerThis is a Headgum podcast. Advertise on Why Won't You Date Me? via Gumball.fm.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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    51 mins