Dating after a Major Scandal (w/ Monica Lewinsky)
Why Won't You Date Me? with Nicole Byer
Headgum & Nicole Byer
4.8 • 15.6K Ratings
🗓️ 1 August 2025
⏱️ 59 minutes
🧾️ Download transcript
Summary
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
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Transcript
Click on a timestamp to play from that location
| 0:00.0 | This is a headgum podcast. |
| 0:05.2 | Want to watch this episode? |
| 0:06.9 | Catch the full video on YouTube. |
| 0:08.9 | Just hit the link in the episode description. |
| 0:14.5 | Why won't you date me? |
| 0:20.6 | Why won't you date me? Why won't you date me? Why won't you date me? Why won't you date me? Please tell me why. |
| 0:32.6 | Ooh, baby, welcome to another episode of Why Won't You Date Me? |
| 0:42.0 | A podcaster, me, Nicole Byer, was trying to figure out why I was so single, even though you could take me on a hot air balloon and leave me in the sky. |
| 0:45.3 | It's our 400th episode. |
| 0:48.0 | Can you believe it? |
| 0:49.1 | I've been talking for seven and a half years. |
| 0:53.1 | It's too long. |
| 0:55.1 | And for a milestone like this, |
| 0:56.8 | I wanted a guest to embody resilience, reflection, |
| 0:59.7 | and the power of reclaiming your own story. |
| 1:02.8 | She's lived through kind of a media firestorm that it was bad, |
| 1:07.2 | and I wouldn't want it. |
| 1:08.4 | And she's come out on the other side as a writer, a speaker, |
| 1:11.0 | an advocate for change. And she's the host of a new podcast called Reclaiming Unwondry. It's Monica |
| 1:18.4 | Lewinsky. I want to wake up to that introduction every morning. I think I would have a very, |
| 1:26.3 | you know, like that's the way to start the day. |
| 1:28.6 | Right. Isn't it fun? When someone just like yells nice things about you? Yeah. And congratulations |
... |
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