Before she was an activist, Monica Lewinsky was the most publicly shamed woman in America. Now, she's reclaiming her story, and her dating life. For the 400th episode of Why Won’t You Date Me?, Monica joins Nicole to talk about dating after a major scandal, being labeled “unmatchable” on eHarmony, and learning to enjoy life when pop culture won’t stop referencing you. She reflects on hosting the wild early-2000s reality show Mr. Personality, shares the worst dates she’s ever had (including ones she walked out on), and even offers up the exact scripts she uses when there’s just no spark. Plus, stick around to the very end as Nicole gets a little reflective on what 400 episodes of the show have meant to her. Check out Monica's podcast, Reclaiming with Monica Lewinsky. Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcast Support this podcast and get discounts by checking out our sponsors: » Green Chef: Make this summer your healthiest yet with Green Chef. Head to Greenchef.com/50DATEME and use code 50DATEME to get 50% off your first month, then 20% off for two months with free shipping. » Smalls: Protein packed cat food! For a limited time only, get 60% off your first order PLUS free shipping when you head to Smalls.com and use code DATEME. » Mint Mobile: This year, skip breaking a sweat AND breaking the bank. Get your summer savings and shop premium wireless plans at mintmobile.com/DATEME. View all of our sponsors and discounts codes at wwydm.notion.site/sponsors. Follow: 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.

Exciting news from Nicole: Best Friends is BACK and 1) now on Headgum, 2) with FULL VIDEO EPISODES! Enter the pantheon of best friendship and check out Nicole and Sasheer's first episode back, available now on Apple Podcasts, Spotify, or wherever you get your podcasts. New episodes every Wednesday. Subscribe to the Best Friends YouTube channel https://youtube.com/@NicoleandSasheer for video episodes. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Comedian Devon Walker (SNL) joins Nicole to tell the story of how he met his girlfriend on a live blind date podcast. He figured it was just a bit - until the audience voted for them to win an Applebee’s gift card and that turned into their actual first date. 3 years later, they’re still together! He and Nicole also talk about the woman who went viral eating 48 oysters on a first date, why it’s a red flag if your partner suddenly starts doing open mics, and how it feels when people send you unsolicited sex tapes in the DMs. Devon shares the absolute nightmare of trying to break up with someone who flooded his phone with scroll-after-scroll of chaotic texts. Plus: He shares the SNL sketch he’s dying to get on air, and they do a deep dive into the food mascot universe - who’s comforting, who’s cursed, and why the Bubba Gump shrimp must be stopped. Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcast Check out Devon's podcast, My Favorite Lyrics with Devon Walker. Support this podcast and get discounts by checking out our sponsors: » Squarespace: Build the website of your dreams! Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME. » Quince: Give your summer closet an upgrade—with Quince! Go to Quince.com/dateme for free shipping on your order and 365-day returns. » Mint Mobile: This year, skip breaking a sweat AND breaking the bank. Get your summer savings and shop premium wireless plans at mintmobile.com/DATEME. View all of our sponsors and discounts codes at wwydm.notion.site/sponsors. Follow: 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.

Comedian and friend Josh Sharp (Dicks: The Musical) returns to the podcast! Nicole and Josh kick things off by reminiscing about the chaotic live show where Nicole interviewed a man in the audience she had slept with. From there, they get into Josh’s foolproof flirting strategy at the club, Annabelle the haunted doll’s cursed tour across America, attending a Big Dick contest, and Josh’s near-death experience in Puerto Vallarta that left him facedown in the ocean with no memory of his own name. They also discuss the realities and benefits of open relationships, how to quiet negative self-talk while dating, and the dangers of eating straight men’s ass. Fun times! In New York? Get tickets to Josh Sharp's show, Ta-da! at joshsharptada.com. Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcast Support this podcast and get discounts by checking out our sponsors: » Betterhelp: Visit Betterhelp.com/DATEME today to get 10% off your first month of therapy. » Wayfair: Wayfair. Every Style, Every Home. » Mint Mobile: This year, skip breaking a sweat AND breaking the bank. Get your summer savings and shop premium wireless plans at mintmobile.com/DATEME. View all of our sponsors and discounts codes at wwydm.notion.site/sponsors. Follow: 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.

Drag queen icon Meatball is back! She and Nicole get into it all - being in her top era, loving the single life, and having weekend boyfriends in different cities. But also... why dating is still so hard when you do drag. Meatball opens up about losing guys the second they find out she’s a queen, and how frustrating it is watching her roster shrink because of it. And of course, the wild date stories are endless - projectile vomiting in a car on a date, sucking 3 different dicks in one night (one the size of a beer can), a hookup who did stand-up after sex, and turning down a dude mid-date for turning on fart porn. It's a wild one. Tune in! You can buy Meatball's jarred farts at meatland.bigcartel.com (it is currently sold out) Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcast Support this podcast and get discounts by checking out our sponsors: » Quince: Give your summer closet an upgrade—with Quince. Go to Quince.com/dateme for free shipping on your order and 365-day returns. » 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. » Mint Mobile: This year, skip breaking a sweat AND breaking the bank. Get your summer savings and shop premium wireless plans at mintmobile.com/DATEME. View all of our sponsors and discounts codes at wwydm.notion.site/sponsors. Follow: 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.

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/@WhyWontYouDateMePodcast Support 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/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.

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/@WhyWontYouDateMePodcast Support 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/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.

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/@WhyWontYouDateMePodcast Support 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/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.

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/@WhyWontYouDateMePodcast 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  » 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/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.

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/@WhyWontYouDateMePodcast Support 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/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.