Dating after a Major Scandal (w/ Monica Lewinsky)

Dating after a Major Scandal (w/ Monica Lewinsky)

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:

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View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.


Follow:

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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.


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Role-Playing (w/ Rachel Bloom)

Role-Playing (w/ Rachel Bloom)

"Good role-playing is just bad improv"Rachel Bloom (Crazy Ex-Girlfriend) has an open discussion about finding therapy and using medication to treat mental health. She also discusses why improvisers should not role-play in the bedroom. As kids, Nicole and Rachel both had imaginary friends they would have sex with. Nicole's given up on dating and considers dating a ghost. She also describes her love for cocaine.Be sure to check out Crazy Ex-Girlfriend on CW!You can play along and see Nicole's Tinder bio and photos on her Facebook page at: https://www.facebook.com/pg/NicoleByerComedyBe 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/tourdatesTwitter: @nicolebyerInstagram: @nicolebyerFacebook: www.facebook.com/nicolebyercomedySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

18 Jan 201953min

Seeking Professional Advice (w/ Dr. Chris Donaghue)

Seeking Professional Advice (w/ Dr. Chris Donaghue)

Dr. Chris Donaghue (Host of Loveline, sex and relationship therapist) provides Nicole with an honest assessment why she may be single. He provides her relationship advice and a Tinder bio makeover. He also shares how to manage dating multiple people at once, the importance of sharing your needs and kinks with your partner, and the importance in masturbating in this sex-positive episode!Thank you to TENGA and Dr. Chris for providing Nicole with the beautiful sex toy giftbasket.You can play along and see Nicole's Tinder bio and photos on her Facebook page at: https://www.facebook.com/pg/NicoleByerComedyBe 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/tourdatesTwitter: @nicolebyerInstagram: @nicolebyerFacebook: www.facebook.com/nicolebyercomedySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

11 Jan 201944min

Finding your S/O's Pet Name (w/ Elizabeth Ho)

Finding your S/O's Pet Name (w/ Elizabeth Ho)

Did you know that couples with pet names statistically have longer lasting relationships? In today's episode, Nicole and Elizabeth Ho (Disjointed) consider what pet name they would want to have. Elizabeth discusses what it's like being in a competitive relationship with your S/O, and Nicole's providing relationship advice to fans over DMs.You can play along and see Nicole's Tinder bio and photos on her Facebook page at: https://www.facebook.com/pg/NicoleByerComedyBe 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/tourdatesTwitter: @nicolebyerInstagram: @nicolebyerFacebook: www.facebook.com/nicolebyercomedySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

4 Jan 201947min

Scheduling Your Booty Calls (w/ Raiza Licea)

Scheduling Your Booty Calls (w/ Raiza Licea)

"If you're busy, you need to book a dick appointment"Raiza Licea (UCB) agrees that life is busy and sometimes you just gotta book time for a dicking. Nicole goes on a wild date with her Lyft driver, and reads her latest failed Tinder conversations. Nicole also discusses some crazy kinks and reveals a few of her own.You can play along and see Nicole's Tinder bio and photos on her Facebook page at: https://www.facebook.com/pg/NicoleByerComedyBe 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/tourdatesTwitter: @nicolebyerInstagram: @nicolebyerFacebook: www.facebook.com/nicolebyercomedySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

28 Dec 201850min

Dating Gay Twins (w/ Joel Kim Booster)

Dating Gay Twins (w/ Joel Kim Booster)

"I was apart of an orgy on a ship, where I looked over at my friend who was wearing this guy like a fucking bracelet"Joel Kim Booster joins Nicole to discuss their favorite porn narratives, cock and ball torture, and Joel describes his experience dating multiple sets of gay twins. A guy who ghosted Nicole is starting his own dating podcast, and it's not sitting well for her.Check out Joel and Nicole's new Drag Race podcast What the Tuck? on HeadGum! Subscribe wherever you get your podcasts.You can play along and see Nicole's Tinder bio and photos on her Facebook page at: https://www.facebook.com/pg/NicoleByerComedyBe 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/tourdatesTwitter: @nicolebyerInstagram: @nicolebyerFacebook: www.facebook.com/nicolebyercomedySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

21 Dec 201853min

Getting Past Dick Size (w/ Lisa Hanawalt)

Getting Past Dick Size (w/ Lisa Hanawalt)

"He just started sweating so much, that it was like water pouring onto me. And he said it was cause he was sad about his ex-girlfriend."Lisa Hanawalt (Bojack Horseman, Baby Genuises Podcast) discusses how to deal with boring guys, publicly declaring your love (like on this very podcast), and the complex behind needing a big dick for pleasurable sex. Nicole reads her latest dating app conversations and also convinces Lisa to eat Adam Conover's butt.You can play along and see Nicole's Tinder bio and photos on her Facebook page at: https://www.facebook.com/pg/NicoleByerComedyBe 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/tourdatesTwitter: @nicolebyerInstagram: @nicolebyerFacebook: www.facebook.com/nicolebyercomedySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

14 Dec 201853min

Love, Lust, and Infatuation (w/ Baron Vaughn)

Love, Lust, and Infatuation (w/ Baron Vaughn)

"Everyone is doing monogamy. And if you try to cram all those people into one door, someone is gonna get hurt."Baron Vaughn (Corporate, The New Negros) explains LOVE. What it is to be a love addict, and the differences on love, lust, and infatuation. He also shares his experiences being in non-monogamous relationships. Nicole addresses the recent reddit threads, explaining why her comedy is so dick-focused.Check out the New Negroes show on Comedy Central in 2019!You can play along and see Nicole's Tinder bio and photos on her Facebook page at: https://www.facebook.com/pg/NicoleByerComedyBe 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/tourdatesTwitter: @nicolebyerInstagram: @nicolebyerFacebook: www.facebook.com/nicolebyercomedySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

7 Dec 20181h

Nicole Does a Live Tarot Reading (w/ Inessa Frantowski)

Nicole Does a Live Tarot Reading (w/ Inessa Frantowski)

Inessa Frantowski (UCB) performs a live tarot reading for Nicole, and boy, are the results dark. They also discuss at what point in the relationship do you have 'the talk', and changing yourself to attract potential partners. Nicole's giving up and starts scheming up a way to be on 90 Day Fiance.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/tourdatesTwitter: @nicolebyerInstagram: @nicolebyerFacebook: www.facebook.com/nicolebyercomedySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

30 Nov 201856min

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