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Headgum & Nicole Byer

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!

Why Won't You Date Me? with Nicole Byer

Actor Nathan Mitchell (The Boys, Ginny & Georgia) joins Nicole to discuss being in relationship limbo, and why it’s actually great to be on the same page about not being on the same page. He shares the boat date gone horribly wrong when his date air-humped a stranger, a make-out session that left him bloody, and he addresses the theories that his Ginny & Georgia character is AI. Nicole shares her experience with a man who thought a picture of a sandwich was an appropriate thirst trap. Plus, Nathan explains the importance of astrology in dating and gives Nicole a deep-dive birth chart reading that uncovers her karmic weight.

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 and get discounts by checking out our sponsors:

Jones Road: Use code DATEME at jonesroadbeauty.com to get a Free Shimmer Face Oil with your first purchase! #JonesRoadBeauty #ad

Wayfair: Way Day is THE sale to shop the best deals in home – we’re talking up to 80% OFF with fast and FREE shipping on everything! Head to Wayfair.com April 25th through the 27th to shop Way Day.

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. See terms and conditions at https://cash.app/legal/us/en-us/card-agreement. Discounts and promotions provided by Cash App, a Block, Inc. brand. Visit http://cash.app/legal/podcast for full disclosures.

Follow:

All Links: linktr.ee/whywontyoudateme

Tour Dates: linktr.ee/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. 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.

Astrology's Effect in Relationships (w/ Nathan Mitchell)

Actor and director Danielle Fishel (Boy Meets World, Girl Meets World) joins Nicole for a chat about how it felt to be treated as a "sex symbol" in the 90s before she was even an adult. Danielle talks about the gross public countdowns to her 18th birthday, and the trauma of being mocked on her own show for being "fat" at a size 4.

She shares what it was like taking Lance Bass to her high school prom during the absolute peak of *NSYNC, having Sabrina Carpenter and John Mayer in her wedding party, and details a 3-day nightmare date from her matchmaker era that might just be the worst dating story we've ever heard on this podcast. Plus, the sweet story of marrying her high school acquaintance after reconnecting on Twitter 18 years later.

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

Want more Danielle? Check out her many podcasts!

Teen Beat - The show where she interviews other child stars and actors about their upbringings and experiences in the industry.

Pod Meets World - Fishel rewatches Boy Meets World and shares behind-the-scenes stories with her co-stars.

American Idol Official Podcast - Fishel Interviews the eliminated contestants.

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

Support this podcast and get discounts by checking out our sponsors:

» HelloFresh: Go to HelloFresh.com/dateme10fm now to Get 10 Free meals + Free Nutribullet® Ultra Plus+ 2-in-1 Compact Kitchen System (a $189.99 value) on your 3rd box. *Free meals applied as a discount on the first box, new subscribers only, varies by plan. Disclaimer: Must order the 3rd box by May 31st, 2026.

» IQBar: Text DATE to 64000 to get 20% off all IQBAR products, plus FREE shipping. Message and data rates may apply.

» The Man of Many Fathers: Available everywhere audiobooks are sold.

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

» Betterhelp: This show is sponsored by BetterHelp. Visit betterhelp.com/dateme today to get 10% off your first month.

Follow:

All Links: linktr.ee/whywontyoudateme

Tour Dates: linktr.ee/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. 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.

Life as a 90s Sex Symbol (w/ Danielle Fishel)

Comedian Drew Droege (Search Party, Bob's Burgers) joins Nicole for a chat about why you should never blow out your own candle in a relationship, the creepy phenomenon of couples who look like twins, and how pop culture's been romanticized abusive relationships. Drew introduces Nicole to a new hookup app that is basically Yelp for blowjobs, and reads some of the incredible BJ reviews that are written like romance novels. Plus, they break down the new Alexander Skarsgård dom/sub rom-com movie, Pillion.

Los Angeles! See Drew Droege's show, Theatre Idiot at Dynasty Typewriter on April 1st. Get tickets at dynastytypewriter.com/calendar-squad-up?event-id=131942

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

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

Support this podcast and get discounts by checking out our sponsors:

» Jones Road Beauty: Use code DATEME at jonesroadbeauty.com to get a Free Shimmer Face Oil with your first purchase! #JonesRoadBeauty #ad 

» Equip: Learn more about Equip’s virtual eating disorder treatment at equip.health/dateme

» Planned Parenthood: Donate to support Planned Parenthood now at plannedparenthood.org/defend.

» NOCD: If you're struggling with OCD or unrelenting intrusive thoughts, NOCD can help. Book a free 15 minute call to get started: learn.nocd.com/DATEME

» 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. See terms and conditions at https://cash.app/legal/us/en-us/card-agreement. Discounts and promotions provided by Cash App, a Block, Inc. brand. Visit http://cash.app/legal/podcast for full disclosures.

Follow:

All Links: linktr.ee/whywontyoudateme

Tour Dates: linktr.ee/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. 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.

There's a Yelp for BJs (w/ Drew Droege)

Legendary comedian and actress Kym Whitley (Curb Your Enthusiasm, Young and Hungry) joins Nicole to chat about entering their healthy era. She fixes Nicole's hydration habits, shares easy ways she incorporates exercise into her routine, and they discuss their life post-weight loss. Kym shares her wildest dating stories, including jumping an ex's fence in a catsuit and cape, and the televised blind date she had with an unexpected star. Plus, Kym teaches us the lost art of flirting.

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

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

Support this podcast and get discounts by checking out our sponsors:

» Jones Road Beauty: Use code DATEME at jonesroadbeauty.com to get a Free Shimmer Face Oil with your first purchase! #JonesRoadBeauty #ad

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

» MeUndies: Right now as a listener of my show, you can get to get 20% off your first order, plus free shipping at MeUndies.com/DATEME, promo code DATEME.

» Jones: Ready to quit for good? Go to quitwithjones.com/DATEME to start your personalized quitting journey and get 15% off with code DATEME.

» Planned Parenthood: Donate to support Planned Parenthood now at plannedparenthood.org/defend.

Follow:

All Links: linktr.ee/whywontyoudateme

Tour Dates: linktr.ee/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. 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.

Our Healthy Era (w/ Kym Whitley)

Showgirl and drag queen Fantasia Royale Gaga (DIY Dungeon) joins Nicole to discuss her journey to becoming "The Body". Fantasia shares the realities of her dating life, explaining the difference between a man who is genuinely attracted to trans women versus a chaser just looking to fulfill a fetish. She reveals why she uses Grindr like a social media app, and shares experience building a BDSM dungeon.

Plus, Fantasia opens up about the extreme measures strangers take to sneak photos of her in public, the intrusive questions people ask about her body, and surviving religious trauma from a church that literally laid her on the altar to pray the gay away.

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

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

Support this podcast and get discounts by checking out our sponsors:

» Equip: Learn more about Equip’s virtual eating disorder treatment at equip.health/dateme

» Planned Parenthood: Donate to support Planned Parenthood now at plannedparenthood.org/defend.

» NOCD: If you're struggling with OCD or unrelenting intrusive thoughts, NOCD can help. Book a free 15 minute call to get started: learn.nocd.com/DATEME

» 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. See terms and conditions at https://cash.app/legal/us/en-us/card-agreement. Discounts and promotions provided by Cash App, a Block, Inc. brand. Visit http://cash.app/legal/podcast for full disclosures

» Wayfair: Find furniture, decor, and essentials that fit your unique style and budget. Head to Wayfair.com right now to shop all things home.

Follow:

All Links: linktr.ee/whywontyoudateme

Tour Dates: linktr.ee/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. 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.

Having "The Body" (w/ Fantasia Royale Gaga)

Drag queen Sapphira Cristál (Drag Race S16) joins Nicole for an educational chat about being a dom, impact play, and the 12-hour prep cycle for bottoming - including how to douche properly and the secret medication trick for staying clean through the night.

Sapphira tells the story of how she met her partner through an Instagram gym thirst trap originally meant for another drag queen, and the time she gave a blowjob so good that a man wrote a song about it.

See Sapphira on tour! Get tickets at seesapphira.com

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

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

Support this podcast and get discounts by checking out our sponsors:

» Cozy Earth: Discover how care in every detail transforms simple routines into moments of true comfort and ease. Head to cozyearth.com and use my code DATEME for up to 20% off. And if you get a Post-Purchase Survey, be sure to mention you heard about Cozy Earth right here!

» HelloFresh: Go to HelloFresh.com/dateme10fm to Get 10 free meals + a FREE Zwilling Knife (a $144.99 value) on your third box. *Offer valid while supplies last. Free meals applied as discount on first box, new subscribers only, varies by plan.

» Equip: Learn more about Equip’s virtual eating disorder treatment at equip.health/dateme

» Planned Parenthood: Donate to support Planned Parenthood now at plannedparenthood.org/defend.

» NOCD: If you're struggling with OCD or unrelenting intrusive thoughts, NOCD can help. Book a free 15 minute call to get started: learn.nocd.com/DATEME

» 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

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. 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.

Being a Dom (w/ Sapphira Cristál)

Legendary drag and meme queen Jasmine Masters (Drag Race S7, All-Stars 4) joins Nicole for a chat about being high for most of Drag Race season 7 and exactly how she snuck weed into the show. Jasmine spills on the origins of her viral "And I Oop-" video and recounts her absolute WORST hookup ever. Plus, we hear about the time her friends accidentally threw her a sold-out meet-and-greet at an Olive Garden on her birthday, and her strict rules for taking care of bad feet.

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

Support this podcast and get discounts by checking out our sponsors:

» Cozy Earth: Share a little extra love this February and wrap yourself—or someone you care about—in comfort that truly feels special. Head to cozyearth.com and use my code DATEME for up to 20% off. And if you get a Post-Purchase Survey, be sure to mention you heard about Cozy Earth right here!

» Jones: Ready to quit for good? Go to quitwithjones.com/DATEME to start your personalized quitting journey and get 15% off with code DATEME.

» Equip: Learn more about Equip’s virtual eating disorder treatment at equip.health/dateme

» Planned Parenthood: Donate to support Planned Parenthood now at plannedparenthood.org/defend.

» NOCD: If you're struggling with OCD or unrelenting intrusive thoughts, NOCD can help. Book a free 15 minute call to get started: learn.nocd.com/DATEME

» 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. See terms and conditions at https://cash.app/legal/us/en-us/card-agreement. Discounts and promotions provided by Cash App, a Block, Inc. brand. Visit http://cash.app/legal/podcast for full disclosures.

Follow:

All Links: linktr.ee/whywontyoudateme

Tour Dates: linktr.ee/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. 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.

Worst Hookup EVER (w/ Jasmine Masters)

Comedian and drag queen Nicholas Scheppard (Very Gay Paint, Art to Me) is fresh out of a breakup. He joins Nicole for a chat about the uphill climb out of it, why working with an ex-boyfriend is absolute torture, and the haunting theory that your partner will tell you exactly how they'll break your heart in the first week. Nicole shares the messy story about a situationship who didn't believe in monogamy, and her obsession with her Ninja Creami.

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

Check out Nicole's episode of ART TO ME. 

Follow Trudy Tective's journey to catch her sister's murderer at @trudy.tective.

Support this podcast and get discounts by checking out our sponsors:

» MeUndies: Right now as a listener of my show, you can get to get 20% off your first order, plus free shipping at MeUndies.com/DATEME, promo code DATEME.

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

» IQBAR: Text DATE to 64000 to get 20% off all IQBAR products, plus FREE shipping. Message and data rates may apply.

» Wayfair: Get organized, refreshed, and back on track this new year for WAY less. Head to Wayfair.com right now to shop all things home.

» Equip: Learn more about Equip’s virtual eating disorder treatment at equip.health/dateme

» Planned Parenthood: Donate to support Planned Parenthood now at plannedparenthood.org/defend.

Follow:

All Links: linktr.ee/whywontyoudateme

Tour Dates: linktr.ee/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. 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.

The Torture of Working with an Ex (w/ Nicholas Scheppard)

Happy Galentine's Day! Comedian and best friend Sasheer Zamata (SNL, Best Friends) returns to the podcast to celebrate the most important relationship of all: female friendship. They do a quick catch up on Sasheer's love life, learn the origins and meaning behind Galentine's Day, and discuss the intimacy of female friendships that you just can't get from a romantic partner. They share some of their favorite Valentine's Day activities, and recount some of their recent dates together, including getting their tarot cards read, taking a jewelry making class and the time they got too high and went to Burger King.

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

Follow:

All Links: linktr.ee/whywontyoudateme

Tour Dates: linktr.ee/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. 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.

Celebrating Galentine's Day (w/ Sasheer Zamata)

Drag queen icon Heidi N Closet (RuPaul's Drag Race S12, All Stars 8) is dressed up like Jesse from Pokemon to geek out over her favorite anime and spill on her beef with Nicki Minaj. Heidi opens up about the rules that keep her open relationship working and shares stories from her pre-fame jobs, including the time she cleaned literal shit at a gas station and the reason she got fired from a hospital. They also discuss her favorite sex move called "The Finisher" and her love of being watched, while Nicole shares the time she sat on a man's face for money.

Check out Heidi N Closet's YouTube channel: youtube.com/@HeidiNClosetOfficial

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

Support this podcast and get discounts by checking out our sponsors:

» HelloFresh: Go to HelloFresh.com/dateme10fm to Get 10 free meals + a FREE Zwilling Knife (a $144.99 value) on your third box. *Offer valid while supplies last. Free meals applied as discount on first box, new subscribers only, varies by plan.

» Function: Own your health for $365 a yea. Learn more and join using my link. Visit functionhealth.com/DATEME and use gift code DATEME for a $25 credit toward your membership.

» Planned Parenthood: Donate to support Planned Parenthood now at plannedparenthood.org/defend.

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

» NOCD: If you're struggling with OCD or unrelenting intrusive thoughts, NOCD can help. Book a free 15 minute call to get started: learn.nocd.com/DATEME

» Betterhelp: This show is sponsored by BetterHelp. Visit betterhelp.com/dateme today to get 10% off your first month.

Follow:

All Links: linktr.ee/whywontyoudateme

Tour Dates: linktr.ee/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. 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.

I Want You to Watch (w/ Heidi N Closet)

Dan Lippert (UCB Comedy, Comedy Bang Bang) joins us to talk about Nicole's abandonment issues, the time she blew him in a bathroom, and Nicole shares the time she slept with a guy with a literal BROKEN dick.

You can play along and see Nicole's Tinder bio and photos on her Facebook page at:

https://www.facebook.com/pg/NicoleByerComedy

Be sure to rate Why Won't You Date Me 5-stars on Apple Podcasts. Leave a dirty comment for a chance have it read on-air.

Follow Nicole Byer:

Tour Dates: nicolebyerwastaken.com/tourdates

Twitter: @nicolebyer

Instagram: @nicolebyer

Facebook: www.facebook.com/nicolebyercomedy

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Bad Hookups (w/ Dan Lippert)

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