I Was a Time Out Magazine Bachelor (w/ Lauren Ashley Smith)

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 minutes withDimension 20, being a “silly billy” on dates, and the moment Lou realized bits don’t always land on dates when you’re trying to build intimacy. They also bond over the guilty thrill of watching other couples on visibly bad dates, and the drama they've witnessed unfold one table over. Plus, Lou reminds Nicole that they once dated. Nicole completely forgot. He gives an honest review of what it was like to date her, and why there was never a second date. Y'all, it's a wild one.Check out Lou Wilson's podcast, Worlds Beyond Number.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» CashApp: Download Cash App Today: https://capl.onelink.me/vFut/3v6r90n6 #CashAppPod *Referral Reward Disclaimer: As a Cash App partner, I may earn a commission when you sign up for a Cash App account.View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This 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.

Actress Jessica Lowe (The Righteous Gemstones, Minx, Wrecked) joins Nicole to share the romantic saga of falling in love on a Second City cruise ship. On the ship, she met a British bassist who became her cruise ship boyfriend - whom she later realized wasn’t as smart as she thought his accent sounded (he tried to dry his pants on a ceiling fan and designed a nightmare demon tattoo for himself).Jessica recalls dating a Dutch chef with a penis that was “too much!” and recounts what might be the most romantic first date ever told on the podcast. She reflects on the men who surprised her, disappointed her, and the slow work of building a relationship that actually lasted.Plus, Jessica and Nicole reminisce about the chaos of filming Curse Friends when everyone tested positive for COVID - and Nicole opens up about sobbing in a makeup chair over a man who simply wasn’t worth it.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» OneSkin: OneSkin is redefining the aging process with their proprietary OS-01 peptide. Get 15% off OneSkin with the code DATEME at https://www.oneskin.co/ #oneskinpod» SquareSpace: Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME.» Booking.com: Book now at Booking.com!» Smalls: Give your cat the food they deserve. For a limited time only, get 60% off your first order PLUS free shipping when you head to Smalls.com and use code DATEME.View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This 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.

TV writer Lauren Ashley Smith (A Black Lady Sketch Show, Smith Sisters Live) joins Nicole to talk about how she met her wife the old-fashioned way - through Time Out New York’s Singles issue.Lauren reveals the strange public response to being a “bachelor” in a magazine, how her wife was one of the only white women working at BET, and the complications that came with planning an interracial lesbian wedding.She also recalls a bizarre school Valentine’s Day test that matched students based on compatibility, and she and Nicole discuss who gets to keep the friends after a breakup. Plus, Nicole gets a magical hot massage and somehow walks away being fluent in Greek.And Lauren shares one big piece of dating advice: why straight people should try dating more like lesbians -letting go of the gender roles getting in the way.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» OneSkin: OneSkin is redefining the aging process with their proprietary OS-01 peptide. Get 15% off OneSkin with the code DATEME at https://www.oneskin.co/ #oneskinpod» EarnIn: Make Any Day Payday! When you download the EarnIn app, type in Why Won't You Date Me under PODCAST when you sign up – it’ll really help the show. » Booking.com: Book now at Booking.com!» Wayfair: Wayfair. Every Style, Every Home.View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This 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.

Actor Michael Urie (Shrinking, Ugly Betty) joins Nicole to discuss the wild hookup culture at Julliard, and the love triangle he had that went sour. Once he got fame from Ugly Betty, he starts going on dates with people who only seem interested in the version of him they saw on TV, until a second shot with actor Ryan Spahn turns into a 17-year partnership. He tells the story of a friend who died singing Britney Spears at karaoke, and lists the surprisingly beautiful ways other pals have died. Plus, the time his dog blew up an airplane bathroom.Michael offers blunt advice for singles: your standards aren’t too high, they’re just too specific, and urges to drop the blinders on your dating life.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» Quince: Treat your closet to a little summer glow-up with Quince. Go to Quince.com/dateme for free shipping on your order and 365-day returns » Mint Mobile: Get your summer savings and shop premium wireless plans at mintmobile.com/DATEME.» SquareSpace: Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME.» BetterHelp: This episode is brought to you by BetterHelp. Give online therapy a try at betterhelp.com/DATEME and get on your way to being your best self.» EarnIn: Make Any Day Payday! When you download the EarnIn app, type in Why Won't You Date Me under PODCAST when you sign up – it’ll really help the show. » ZocDoc: Zocdoc.com/DATEME to find and instantly book a top-rated doctor today.» Booking.com: Book now at Booking.com!View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This 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.

Comedian and friend Betsy Sodaro (Ghosts, A Funny Feeling) joins Nicole to swap crazy Las Vegas stories, their experience getting slammed by puberty, and debate why we shouldn’t have to pay taxes right now (plus what happened when Nicole skipped paying taxes for 5 years). Betsy reveals what life was like spending six months in a hotel, and Nicole confesses she nearly launched an anime-recap podcast with an ex. Plus: the time a customer-service call at Lane Bryant turned into phone sex.WATCH this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» Smalls: Protein packed cat food! For a limited time only, get 35% off plus an additional 50% off your first order when you head to Smalls.com and use code DATEME.» Equip: To learn more about Equip's virtual eating disorder treatment, visit Equip.Health/dateme» EarnIn: Make Any Day Payday! When you download the EarnIn app, type in Why Won't You Date Me under PODCAST when you sign up – it’ll really help the show.» Booking.com: Book now at Booking.com!View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This 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.

Actress Edi Patterson (The Righteous Gemstones) joins Nicole to talk about falling in love with her improv teacher, hiding their relationship from the world, and mistaking his proposal for a joke. She opens up about being a late bloomer in dating, throwing house parties that felt straight out of a '90s film, and the one dating lesson she learned from a kid that she wishes everyone would follow. Plus: ghosting guilt, cringey first date stories, 90 Day: Hunt for Love, and the time Nicole’s dog showed up on a stranger’s Instagram story.WATCH this episode here: https://youtu.be/j9aKyd_PtzISupport this podcast and get discounts by checking out our sponsors:» SquareSpace: Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME.» EarnIn: Make Any Day Payday! When you download the EarnIn app, type in Why Won't You Date Me under PODCAST when you sign up – it’ll really help the show.» Booking.com: Book now at Booking.com!View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This 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.

Actress Rose McIver (Ghosts, iZombie, voice of Headgum) joins Nicole to explain New Zealand, why she doesn’t post her loved ones on social media, and talk about all the cute, funny other ways people show love. They get into weird animal relationship stories, like the woman in love with a dolphin (who died of heartbreak), the man who tried to live among grizzlies, and Nicole’s dream of becoming queen of the whales. Plus: a simple dinner hosting hack from Meghan Markle.WATCH this episode here: https://youtu.be/gdfc4IbNLv8Support this podcast and get discounts by checking out our sponsors:» Equip: To learn more about Equip's virtual eating disorder treatment, visit Equip.Health/dateme» Cash App: Download Cash App Today: https://capl.onelink.me/vFut/3v6r90n6 #CashAppPod *Referral Reward Disclaimer: As a Cash App partner, I may earn a commission when you sign up for a Cash App account.View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This 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.

Bob the Drag Queen (The Traitors, winner of RuPaul's Drag Race S8) returns to the podcast to derail the show. This time, Bob interviews Nicole about her current relationship, run through their plans to prep for tariffs, and discuss LA's newest serial killer. He sniffs out the ulta-rich cast members on The Traitors, shares what he hates about Italy, and Canada’s ex-prime minister's blackface scandal. Plus, Nicole shares her latest showdown with the cops.Buy Bob's new book, Harriet Tubman: Live in Concert at readthedragqueen.com.WATCH this episode at youtu.be/ZojW_xiV2sMSupport this podcast and get discounts by checking out our sponsors:» OneSkin: Get 15% off OneSkin with the code DATEME at oneskin.co #oneskinpod» SquareSpace: Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME.» Wayfair: Every Style, Every Home.View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This 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.

TikTok star Drew Afualo joins Nicole to share her enemies‑to‑lovers love story and the worst dates that taught her to trust her gut. She tells the time she dated a man who drank ocean water and ended up getting his stomach pumped, walks through her viral list of red flags in men, and the backlash she received online for sharing it. They dig into the male loneliness epidemic, red‑pill culture, and what we can learn from the dating on Love On The Spectrum. Plus, Nicole tells the time she accidentally went on a beach date with a 60‑year‑old comedian, and the story of how banana bread uncovered an affair.Watch this episode here: https://youtu.be/mM7FvATy35gWrite Nicole a dirty message! Send it to [email protected] with the subject line "Dirty Message" and Nicole may read it in a future episode.Support this podcast and get discounts by checking out our sponsors:» Quince: Treat your closet to a little summer glow-up with Quince. Go to Quince.com/dateme for free shipping on your order and 365-day returns.» Equip: To learn more about Equip's virtual eating disorder treatment, visit Equip.Health/dateme» BetterHelp: This episode is brought to you by BetterHelp. Give online therapy a try at betterhelp.com/DATEME and get on your way to being your best self.View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This 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.

Comedian and Nicole's fictional boyfriend Colton Dunn (Superstore, Grand Crew, Key and Peele) joins Nicole to talk about dating customs in Europe (and what we can learn from them), getting mad at your partner over what they did in your dream, and what surprised him most about becoming a dad. He reflects on why improv might never be cool- even if you're good at it, and shares behind-the-scenes stories from some of the most iconic Key & Peele sketches. Plus: diaper blowouts, fake babies at Disneyland, and getting called the "Black Seth Rogen."Watch this episode here: https://youtu.be/qYOWub9maa0Write Nicole a dirty message! Send it to [email protected] with the subject line "Dirty Message" and Nicole may read it in a future episode.Support this podcast and get discounts by checking out our sponsors:» ZocDoc: Stop putting off those doctors appointments and go to Zocdoc.com/DATEME to find and instantly book a top-rated doctor today.» Sorry I Missed This: Search for “Sorry I Missed This” in your favourite podcast app! https://lnk.to/sorryimissedthisPSView all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This 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.