Dating after a Major Scandal (w/ Monica Lewinsky)
Why Won't You Date Me? with Nicole Byer1 Aug 2025

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

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