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.


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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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Dating Dogs and Werewolfs (w/ Justin Simien)

Dating Dogs and Werewolfs (w/ Justin Simien)

"When he came, did he go AWOOO?"Justin Simien (Creator of Dear White People) joins Nicole to talk about the kinkiest thing he's ever done, teach her about gay "puppy-pack" arrangements, and Nicole shares a story about dating a werewolf.Plus, Nicole's dogs are eating her weed, and she expresses her thoughts on Logan Paul.Be sure to check out the new season of Dear White People on Netflix!You can play along and see Nicole's dating app profiles and photos on her Facebook 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 to have it read on-air.Follow Nicole Byer:Tour Dates: nicolebyerwastaken.com/tourdatesTwitter: @nicolebyerInstagram: @nicolebyerFacebook: www.facebook.com/nicolebyercomedyBuy Merch: https://www.teepublic.com/stores/nicole-byer?ref_id=9649See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

16 Aug 20191h 8min

The Joy of Being Alone (w/ Ashley Nicole Black)

The Joy of Being Alone (w/ Ashley Nicole Black)

"I would love for Guy Fieri to narrate my sex"Ashley Nicole Black (Full Frontal with Samantha Bee, A Black Lady Sketch Show) joins Nicole to share her love of being alone, whether they like to play music during sex, and Nicole's dream anniversary date.Also, Ashley exclusively dated gay guys in high school, meanwhile Nicole's was asking her gay friend to help lose her virginity.Be sure to check out A Black Lady Sketch Show on HBO!This was recorded live in Montreal at Just for Laughs.You can play along and see Nicole's dating app profiles and photos on her Facebook 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 to have it read on-air.Follow Nicole Byer:Tour Dates: nicolebyerwastaken.com/tourdatesTwitter: @nicolebyerInstagram: @nicolebyerFacebook: www.facebook.com/nicolebyercomedyBuy Merch: https://www.teepublic.com/stores/nicole-byer?ref_id=9649See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

9 Aug 20191h

Power-Bottom (w/ Monique Heart)

Power-Bottom (w/ Monique Heart)

"I thought I had contracted an STD where I was rotting from the inside"Drag queen Monique Heart (RuPaul's Drag Race Season 10, All Stars Season 4) has never been in a real relationship. He shares his experiences with growing up in a religious upbringing, the girl he once wanted to marry, and his fear of the new wave of STDs. Also, they dive into their kinks and all the crazy public places they've done it.Plus, Nicole keeps walking in on her friends having sex, and is getting prepositioned threesomes from fans.Pre-order Monique's new EP/Biography today!You can play along and see Nicole's dating app profiles and photos on her Facebook 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 to have it read on-air.Follow Nicole Byer:Tour Dates: nicolebyerwastaken.com/tourdatesTwitter: @nicolebyerInstagram: @nicolebyerFacebook: www.facebook.com/nicolebyercomedyBuy Merch: https://www.teepublic.com/stores/nicole-byer?ref_id=9649See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

2 Aug 20191h 8min

Making a Polyamorous Relationship Work (w/ DeRay Davis)

Making a Polyamorous Relationship Work (w/ DeRay Davis)

DeRay Davis (Snowfall, 21 Jump Street) has lived a polyamorous relationship with 2 women for most of his life. He explains how he introduces it to his partners, how to show respect to the parents, and how they make their atypical relationship work. DeRay breaks the stigma on polyamorous relationships and shares how him and his partners live together, vacation together, and sleep together.Plus, Nicole tries to sleep with an audience member after a live show - and boy did it not go well.You can play along and see Nicole's dating app profiles and photos on her Facebook 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 to have it read on-air.Follow Nicole Byer:Tour Dates: nicolebyerwastaken.com/tourdatesTwitter: @nicolebyerInstagram: @nicolebyerFacebook: www.facebook.com/nicolebyercomedyBuy Merch: https://www.teepublic.com/stores/nicole-byer?ref_id=9649See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

26 Juli 201950min

A Boyfriend for Every Stage of your Life (w/ Jessica McKenna)

A Boyfriend for Every Stage of your Life (w/ Jessica McKenna)

Jessica McKenna (Off Book podcast) has had a boyfriend in every stage of her life. She details the drama behind her middle school romance, to meeting boys in high school mock trial, and charming her current man with her Disneyland bathroom knowledge. Nicole shares a moment she had with a homeless man, and shares her story of sexual assault in public.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/nicolebyercomedyBuy Merch: https://www.teepublic.com/stores/nicole-byer?ref_id=9649See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

19 Juli 20191h 4min

Microdosing (w/ Johnny Pemberton)

Microdosing (w/ Johnny Pemberton)

"I thought I was going to die. I was actually laughing at the idea of living."Johnny Pemberton (22 Jump Street, Superstore) discusses taking LSD at Disneyland, and accidentally overdosing while trying to microdose. Meanwhile, Nicole's candy-flipping and wants to start microdosing shrooms.Plus, Nicole goes over some of her latest awkward dating app conversations, and Johnny suggests some new wild dating tips for Nicole to try out.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.

12 Juli 201954min

Nicole's Choice of Porn (w/ Ronnie Adrian)

Nicole's Choice of Porn (w/ Ronnie Adrian)

"I'm crazier than you. I'll fuck you up with these dildos"Ronnie Adrian (Comedy Bang Bang, White Women) joins Nicole to discuss their mutual struggle with flirting, and the best way to end a bad date with courtesy. Nicole shares her favorite porn videos to masturbate to, and calls out a woman for peeing on her toilet seat.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.

5 Juli 201959min

The Opposite of a Meet-Cute (w/ Alice Wetterlund)

The Opposite of a Meet-Cute (w/ Alice Wetterlund)

Alice Wetterlund (Girl Code, Treks and the City podcast) joins Nicole to discuss their Girl Code tour horror stories, talk about men who claim to have dated celebrities (we're talking about YOU, Moby) and Alice's newfound interest in butt stuff. Plus, Nicole shares details on her new book deal!You can email Nicole at baconcansave@gmail.com. Nicole might respond if she's drunk.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 Juni 20191h

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