Headgum & Nicole Byer

Why Won't You Date Me? with Nicole Byer

Society EN ↓ 457 episodes

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!

Author

Headgum & Nicole Byer

Category

Society

Podcast website

headgum.com

Latest episode

Jul 10, 2026

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Episodes

Attached (w/ Brittani Nichols) 15.10.2021

Comedian and writer Brittani Nichols ( A Black Lady Sketch Show ) chats with Nicole about recognizing different adult attachment styles in relationships, how her relationship sparked by a DM slide asking "Who's that zaddy?", and discusses why it's healthy to date multiple people at once. Plus, Nicole plays dead on a date. Black Lives Matter. Click here for a list of over 100 different ways you can...

Second Puberty (w/ Carter Ray) 08.10.2021

Filmmaker  Carter Ray  ( The Change Up ) chats with Nicole about their experience going through a 2nd puberty while on hormones, the challenges they faced coming out while attending a Christian high school, and the difference in dating women as a lesbian vs as a trans man. Carter shares his goal to reshape the representation of trans people seen on-screen. Black Lives Matter. Click here for a list...

Pooping Together (w/ Meghan Trainor and Ryan Trainor) 01.10.2021

Does the couple that poop together, stay together? Grammy-award winning singer-songwriter Meghan Trainor and brother Ryan Trainor (co-hosts of Workin on It' ) discuss the special relationship that's bonded over pooping. Meghan confesses she had 2 toilets installed in her bathroom so her and her husband can poop together. Ryan shares how the pandemic lead him to sobriety. They also discuss dating r...

Awkward Sex Talk (w/ Crystal Methyd) 24.09.2021

Drag queen Crystal Methyd ( RuPaul's Drag Race S12) joins Nicole to chat about their most romantic date, getting the 'sex talk' at the age of 22, and debates if you should text your date back immediately. They also discuss their journey into drag, finding their drag aesthetic, and their experience shooting Drag Race in the middle of the pandemic. Meanwhile, Nicole is worried her Netflix show is co...

Playing Hard to Get (w/ Ms. Pat) 17.09.2021

Comedian Ms. Pat chats with Nicole about her time in jail for drug trafficking, shares the secrets behind her 28 years of marriage, and offers advice on how to play hard to get. Plus, Ms. Pat's not happy that Nicole's sleeping around with random audience members, so she decides to set Nicole up with a man. Black Lives Matter. For a list of resources and ways to support, see linktr.ee/nationalresou...

Yelp for Escorts (w/ Alexa Eason) 09.09.2021

Full-service sex worker Alexa Eason shares about her life as an escort. She teaches Nicole about BDSM, the relationship risks involved with sex work, Instagram's censoring of fat bodies, and the dreaded "Yelp for Escorting" sites where escorts are ranked against each other. Alexa gives advice for anyone looking to get started doing sex work. Black Lives Matter. For a list of resources and ways to...

Catfish Catcher (w/ Justin Martindale) 03.09.2021

Comedian Justin Martindale joins Nicole to discuss how their 'summer of love' has been disappointingly dry for the both of them. Justin shares the time he got catfished by a cop, how he deals with chucklefuckers while touring, and the craziness behind the #FreeBritney movement. Plus, what's up with these people getting duct taped on airplanes? Black Lives Matter. For a list of resources and ways t...

Sucking D in the Locker Room (w/ Laganja Estranja) 27.08.2021

Drag queen and choreographer Laganja Estranja ( RuPaul's Drag Race S6 ) joins Nicole to discuss her truth coming out as trans, finding confidence in self-love, the thrill of sucking dick in the high school locker room, and getting off on Grindr messages. Plus, Laganja discusses the injuries she sustains stunting, and answers if she would participate in a future season of RPDR All Stars . For more...

Hot Girl Summer (w/ Lawrence Chaney) 20.08.2021

Drag queen of Scots Lawrence Chaney (winner of RPDR UK S2) chats with Nicole about his dating live after winning Drag Race , how he got banned from Tinder for 'catfishing' as himself, and pitches to host the UK version of Nailed It!. Meanwhile, Nicole's plans for a Hot Girl Summer have gone awry. For more drag queens on WWYDM, check out our episode playlist on Spotify: bit.ly/wwydmdrag Black Lives...

I got 99 problems... palsy is just one (w/ Maysoon Zayid) 13.08.2021

Comedian and actress Maysoon Zayid was born with cerebral palsy. She chats with Nicole about some of the cruel comments she receives about her disability, the struggles comedians of color face in Hollywood, and shares her wild industry rejection stories. Maysoon also advocates why speed-dating is a cost-effective and efficient way of finding love, and helps break down the current Israeli-Palestini...

How to be Intuitive About Your Love Life (w/ Laura Day) 06.08.2021

'Psychic to the stars' and best selling author Laura Day is here to teach Nicole all about intuition and how to develop it. She discusses how she realized she had intuitive powers, coaches how to be intuitive about your own love life, and how to train your pleasure receptors and send out pleasure signals to a potential mate. Black Lives Still Matter! For a list of resources and ways to support, se...

Problem Solving on the Toilet (w/ Yola) 30.07.2021

What a treat. Grammy nominated English musician Yola is here! Nicole and Yola chat about the difference in racism when dating in the UK vs the US, how crying on her motorcycle back from her mother's funeral inspired her songwriting, and how sitting on the toilet can be the best way to solve creative challenges. Check out Yola new album, Stand for Myself , out today. Follow Nicole Byer: Tour Dates:...

Thriving Alone (w/ Harvey Guillén) 23.07.2021

Actor Harvey Guillén ( What We Do in the Shadows ) is single but not quite ready to mingle. He discusses why he guards his profession from his dating life, how he found love on Instagram, and the important need for space in any relationship. Nicole reads some wild dating app profiles. Black Lives Matter. For a list of resources and ways to support, see blacklivesmatters.carrd.co . Follow Nicole By...

Being a Single Mom of 3 (w/ Francesca Amber) 16.07.2021

Nicole’s close friend Francesca Amber (host of Law of Attraction Changed my Life ) talks about the struggles of being a mother of twins, explains the latest fad of 'co-parenting', and describes how to use the Law of Attraction to manifest your dream person. Meanwhile, Nicole counts down the days until her dick appointment. Black Lives Matter. For a list of resources and ways to support, see blackl...

The Cost of Being 'Cute' (w/ Cat Hollis) 09.07.2021

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 blacklivesmatt...

The Power of 'I Love You' (w/ Sam Richardson) 02.07.2021

Actor and comedian Sam Richardson ( Veep, I Think You Should Leave ) chats with Nicole about his success finding love on Raya, wanting kids so he can continue doing kid things, the power of saying 'I love you' first in a relationship, and pitches ideas for dating app opening messages. Black Lives Matter. For a list of resources and ways to support, check out blacklivesmatters.carrd.co . Follow Nic...

Are you 'Love Avoidant'? (w/ Reggie Watts) 25.06.2021

Comedian and musician Reggie Watts ( The Late Late Show with James Corden ) chats with Nicole about his unique eating habits, his time spent playing in a 70's cover band, and the weird shift from being a fake band leader on Comedy Bang! Bang!, to a real band leader for The Late Late Show with James Corden. Nicole learns she may be 'love avoidant'. Black Lives Matter. For a list of resources and wa...

We're living in the wildest times (w/ Jason Concepcion) 18.06.2021

Jason Concepcion (host of Takeline , Binge Mode ) joins Nicole to discuss the culture shock he experienced visiting the Philippines during a coup, how the pandemic revealed America's systemic failures, their favorite small businesses to support, and the WNBA. As America opens back up, Nicole's back in the dating game but it's not going so well. Are dating apps operating fake profiles to keep you e...

Back in the Dating Game (w/ Shea Couleé) 04.06.2021

Drag queen Shea Couleé (Winner of RPDR All Stars 5 ) talks to Nicole about finding love at the club, being a drag mother, wig mishaps, and doing poppers. Plus, Nicole's back in the dating game and it's off to an awkward start. For more Shea & Nicole, check out Nicole's episode on Shea's podcast Wanna Be On Top?  For more drag queens on WWYDM, check out our episode playlist on Spotify: bit.ly/w...

Sleeping with Your Uber Driver (w/ London Hughes) 28.05.2021

Comedian London Hughes (Netflix's To Catch a Dick ) and Nicole chat about her experience moving to America during a pandemic and race war, sleeping with her Uber driver, doggy style techniques, sucking dick, and pitch their new doomsday movie idea. Black Lives Matter! For a list of resources and ways to support, check out blacklivesmatters.carrd.co . Follow Nicole Byer: Upcoming Tour Dates: linktr...

Proposal Gone Wrong (w/ Paul Scheer) 21.05.2021

Comedian and actor Paul Scheer ( The League , Black Monday ) and Nicole chat about how his proposal to June Diane Raphael went terribly wrong, how June's wedding ring was stolen from her finger, and shares good wisdom on the importance of relationship building. Plus, June sits nearby, fact-checking Paul's stories. May 25th See Why Won't You Date Me LIVE featuring Drag Race S11's Miss Congeniality...

Kinky in Public (w/ Jessica Rothe) 14.05.2021

Actress Jessica Rothe ( Happy Death Day, La La Land ) and Nicole discuss if it's OK to do kinky acts in public, the bizarre ways people are monetizing kinks, and the surprising reality of male escorting. Plus, Jessica describes her pandemy micro-wedding, and her major mic-drop "I love you" moment in her relationship. See Why Won't You Date Me LIVE May 25th! Tickets at live.nicolebyerwastaken.com F...

Filming Sex Scenes (w/ Casey Wilson) 07.05.2021

Comedian Casey Wilson ( Happy Endings, SNL ) chats with Nicole about shooting her recent sex scene, exchanges crazy nannying stories, and shares how she met her husband on the set of Happy Endings . Plus, Nicole matched with her Nailed-It camera person and things got weird. Follow Nicole Byer: Upcoming Tour Dates: linktr.ee/nicolebyerwastaken Twitter: @nicolebyer Instagram: @nicolebyer Buy Merch:...

Being 'Sexually Smart' (w/ JB Smoove) 30.04.2021

Comedian, actor, and self-proclaimed 'Love Doctor' JB Smoove ( Curb Your Enthusiasm ) joins Nicole to provide his wisdom on flirting, roller skating, developing rhythm, and shares his guide on having sensual sex. Then, JB elaborates on some motivational quotes. For more of JB’s wisdom, check out his new daily podcast May I Elaborate? Daily Wisdom from JB Smoove. We're nominated for a Webby Award!...

Bad Dating App Bios (w/ Aparna Nancherla) 23.04.2021

Stand-up comedian Aparna Nancherla ( BoJack Horseman , Corporate ) joins Nicole to discuss how her first and only Tinder date evolved into her longterm relationship. They read some bad dating app bios, talk The Real Housewives of Potomac, and Aparna gives advice on preparing for the possibility of a Handmaid's Tale -like apocalypse. We're nominated for a Webby Award! Please cast your vote here: ht...

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