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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

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!

Subscribe to Best Friends for more! https://headgum.com/best-friends.

For more Big Dipper and Meatball, check out their podcast Sloppy Seconds: https://www.everybodysaymom.com/shows/sloppy-seconds

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

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

» Bask & Lather: Explore viral bestsellers and products for healthier hair of ALL types at https://baskandlatherco.com.

» Hinge: Listen to No Ordinary Love for free on Spotify! https://hin.ge/WhyWontYouDateMe

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

» 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.

Check out all of our sponsors and discount codes at wwydm.notion.site/sponsors.

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.

The Most Chaotic Friendship Ever (w/ Meatball and Big Dipper)

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.

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

Support this podcast by checking out our sponsors:

» Audible: Find your next laugh on Audible. Stories that speak to you. New members can start listening with a 30-day free trial at https://Audible.com/DATEME

» Hers: Sponsored by Hers. Visit https://forhers.com/dateme to get a personalized, affordable plan that gets you.

» Hinge: Listen to No Ordinary Love for free on Spotify! https://hin.ge/WhyWontYouDateMe

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

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

Check out all of our sponsors and discount codes at wwydm.notion.site/sponsors.

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.

The AI Dating Dystopia (w/ Jarvis Johnson)

Drag queen superstar Onya Nurve (Winner of RuPaul's Drag Race S17) joins Nicole to talk about the time she was catfished on a dating app by a high school creep! Onya also sets the record straight on her true dynamic with the Season 17 girls, revealing why she felt like an outsider navigating the cast's social circle. She shares how her current girlfriend started out as her college bestie, the friction of taking her on tour as an assistant, and her journey to realizing she was pansexual.

Plus, they debate whether sharing your location is the ultimate red flag, discuss the crazy movie Obsession, and reveal the truth about why Onya was let go from a tour of Kinky Boots just days before opening.

WWYDM is hiring a part-time podcasting apprentice! Learn more and apply here.

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

Support this podcast by checking out our sponsors:

» Hinge: Listen to No Ordinary Love for free on Spotify! https://hin.ge/WhyWontYouDateMe

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

» Chime: Join the millions who are already banking fee free with America’s #1 Choice for Banking. Head to https://Chime.com/dateme. Sign up now. It only takes a few minutes.

» 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.

Check out all of our sponsors and discount codes at wwydm.notion.site/sponsors.

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.

The Catfish Who Wanted to "Teach Me a Lesson" (w/ Onya Nurve)

Nicole's photographer, Kim Newmoney (VOGUE, #VERYFAT #VERYBRAVE) chats with her about the logistics and managing a harem of 7 hot men. They talk about men who claim they want casual relationships but get territorial when another guy whose interest, and Kim shares what it took to walk away from a 7 year relationship with mismatched life goals.

As a professional photographer, Kim drops her advice on taking your dating app profile pictures, getting comfortable on camera, and looking effortlessly sexy. Plus, Kim and Nicole reminisce the guerrila-style shooting behind Nicole's book, #VERYFAT #VERYBRAVE: THE FAT GIRL'S GUIDE TO BEING #BRAVE AND NOT A DEJECTED, MELANCHOLY, DOWN-IN-THE-DUMPS WEEPING FAT GIRL IN A BIKINI.

Buy the book here: https://www.nicolebyerwastaken.com/buy-my-book

WWYDM is hiring a part-time podcasting apprentice! Learn more and apply here.

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

Support this podcast by checking out our sponsors:

» Smileset: Listeners of our show get an additional 35% discount when they go to https://smileset.com/dateme. With this discount, you can get the smile of your dreams for under 13 hundred bucks!

» Hinge: Listen to No Ordinary Love for free on Spotify! https://hin.ge/WhyWontYouDateMe

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

» 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

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

» Chime: Join the millions who are already banking fee free with America’s #1 Choice for Banking. Head to https://Chime.com/dateme. Sign up now. It only takes a few minutes.

Check out all of our sponsors and discount codes at wwydm.notion.site/sponsors.

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.

Juggling A 7-Man Harem (w/ Kim Newmoney)

Comedian Bresha Webb (Run the World, Hacks) joins Nicole to share her terrible experience accientally dating a Hollywood scammer. Bresha also shares the story of a guy who paid for their dinner using a coin purse full of laundry quarters, what happens when you livestream a terrible first date on Instagram so your followers can roast the man, and the incredibly romantic 30-day Zoom courtship that led to her marriage. Plus, Nicole and Bresha reminisce about auditioning for SNL together and discuss the unhinged challenges on Love Island that will definitely haunt those contestants forever.

Check out Bresha's new special, LOL Live with Bresha Webb, on Hulu or Disney+.

WWYDM is hiring a part-time podcasting apprentice! Learn more and apply here.

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

Support this podcast by checking out our sponsors:

» Hers: Sponsored by Hers. Visit forhers.com/dateme to get a personalized, affordable plan that gets you.

» 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. hin.ge/WhyWontYouDateMe

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

» 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.

» Wayfair: Join Wayfair Rewards today to get 5% back on every purchase and start saving on your next home upgrade. Head to Wayfair.com to shop all things home.

Check out all of our sponsors and discount codes at wwydm.notion.site/sponsors.

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.

Dating a Hollywood Scammer (w/ Bresha Webb)

Comedian and writer Eliot Glazer (Broad City, New Girl) returns to the podcast! He shares how a group blind date quickly turned into a one-on-one nightmare with a horrible, drunk Jubilee "celebrity." Plus, Elliot and Nicole talk about what it's like to date an NPC, ask what happened to the whimsy in men's fashion, and discuss learning to be a better gay.

Check out Eliot's new book, The Terrible, Horrible, No Good, Very Bad Gay, out Aug 11th.

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

Support this podcast by checking out our sponsors:

• Hers: Sponsored by Hers. Visit forhers.com/dateme to get a personalized, affordable plan that gets you.

• 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. hin.ge/WhyWontYouDateMe

• Audible: Find your next laugh on Audible. Stories that speak to you. New members can start listening with a 30-day free trial at Audible.com/DATEME

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

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

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

Check out all of our sponsors and discount codes at wwydm.notion.site/sponsors.

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.

The Terrible, Horrible, No Good, Very Bad Date (w/ Eliot Glazer)

Comedian Devon Walker (SNL, Big Mouth) returns to the podcast to join Nicole for a chat about "goblintimacy", the new dating trend where you skip putting your best foot forward. Nicole shares the details of her terrifyingly chaotic NYC taxi ride, the wild energy of the city after the Knicks championship win, and addresses those recent internet comments about her hair. Plus, they conduct a very important investigation into Willem Dafoe's notoriously huge hog, Nicole breaks down the extensive list of Hollywood actors in her romantic "stable," and they discuss the importance of knowing your STD status.

Check out Devon's podcast, My Favorite Lyrics. You can watch Nicole's episode here: youtube.com/watch?v=LnjB1YWatF8

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

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.

The 'Goblintimacy' Dating Trend (w/ Devon Walker)

Drag queen Lydia B Kollins (Drag Race S17, All Stars S10) joins Nicole to spill the behind-the-scenes tea on her iconic Drag Race showmance with Kori King. Find out just how strict production really is when it comes to off-screen flirting, what it was like having their first kiss during a lip sync for your life, plus the reason why she fully ghosted Kori after filming wrapped.

Plus, Lydia opens up about her history of dating women and "dabbling in the puss." She explains why she believes it's easier to love a woman than a man, and why she builds her live shows specifically for her sapphic fans. Finally, hear the story of why RuPaul personally bestowed her with the middle name "Butthole."

Get tickets to her tour with Kori King and Suzie Toot, "ButtTootKing" at ButtTootKing.com.

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

Support this podcast by checking out our sponsors:

• SmileSet: Listeners of our show get an additional 35% discount when they go to smileset.com/dateme. With this discount, you can get the smile of your dreams for under 13 hundred bucks!

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

• Sleep Doctor: Take back your sleep. Find out how at sleepdoctor.com.

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

Check out all of our sponsors and discount codes at wwydm.notion.site/sponsors.

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.

The Truth About TV Showmances (w/ Lydia B Kollins)

Drag queen icon Willam (Drag Race S4, host of Race Chasers) returns! She joins Nicole to break down the mathematical formula for the optimal orgy, the proper etiquette for passing good trade around to your drag sisters, and what really goes down inside LA's underground sex dungeons. Willam also reveals her pro tips for scheduling multiple hookups in one night and confesses the absolute kinkiest thing she's ever done. Plus, hear the hot story of how she met her 6'6" lawyer ex-husband at the door of Micky's, why she turned to OnlyFans to pay her two mortgages, and why she simply has to stop hooking up with the contestants on her new dating show, Love's a Drag.

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

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

• 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.

• Audible: Listen to Heads Will Roll: Heir Apparent, available now on Audible. Go to Audible.com/headswillrollseries to start listening today.

• Wayfair: Ready to upgrade your home for way less? Head to Wayfair.com right now to shop all things home and get your space ready for less.

Check out all of our sponsors and discount codes at wwydm.notion.site/sponsors.

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.

Sharing Trade (w/ Willam Belli)

Drag queen June Jambalaya (Drag Race S14) joins Nicole to discuss hiding her drag career from her dates, being engaged twice, and leaving her fiancé to compete on Drag Race. Plus, Nicole and June discuss the best city to be depressed in, reveal the wildest things they've done to impress a man, and June shares her amazing date after being set up by Kerri Colby.

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

Support 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

• 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.

• Planned Parenthood: Donate to support Planned Parenthood now at PlannedParenthood.org/defend

Check out all of our sponsors and discount codes at wwydm.notion.site/sponsors.

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.

My Career Ruined my Relationships (w/ June Jambalaya)

Cat Hollis led the 2020 Portland Stripper Strike. Here, she explain why it happened and her work for equitable workspaces in the adult industry. Cat discusses the costs of being cute, shares the common challenges people face when dating a stripper, and gives advice on how to feel sexy even after a rejection.

Black Lives Matter. For a list of resources and ways to support, check out blacklivesmatters.carrd.co. 

Follow Nicole Byer: 

Tour Dates: linktr.ee/nicolebyerwastaken 

Twitter: @nicolebyer 

Instagram: @nicolebyer 

Merch: teepublic.com/stores/nicole-byer?ref_id=964

Nicole's book: indiebound.org/book/9781524850746

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

The Cost of Being 'Cute' (w/ Cat Hollis)

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