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Why Won't You Date Me? with Nicole Byer

My Career Ruined my Relationships (w/ June Jambalaya)

Why Won't You Date Me? with Nicole Byer

Headgum & Nicole Byer

Romance, Raya, Sexuality, Interviews, Hookups, Single, Relationship, Sex, Bumble, Nicole Byer, Comedy Interviews, Relationships, Society & Culture, Couples, Love, Hookup, Date, Health & Fitness, Interview, Encounters, Stories, Comedy, Advice, Tinder, Dating, Therapy, Podcast, Dating Apps

4.916K Ratings

🗓️ 10 July 2026

⏱️ 56 minutes

🧾️ Download transcript

Summary

Drag queen June Jambalaya (Drag Race S14) joins Nicole to discuss hiding her drag career from her dates, being engaged twice, and leaving her fiancé to compete on Drag Race. Plus, Nicole and June discuss the best city to be depressed in, reveal the wildest things they've done to impress a man, and June shares her amazing date after being set up by Kerri Colby.


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

Want to watch this episode? Catch the full video on YouTube. Just hit the link in the episode description.

0:07.0

This is a Headgum podcast.

0:10.0

The nice man in my life once planned a surprise trip for us to add a while. And it was unbelievable. He booked a stay on Airbnb and found this absolute dream of an A-frame cabin tucked right into the snowy mountains.

0:23.4

It was gorgeous and sat on this massive private property, which meant my dog Clyde also had a fun vacation roaming the woods all by himself.

0:31.2

Then we finally went into town and discovered Islewile is literally the greatest place on Earth.

0:36.2

Do you know who their mayor is? A golden retriever named Mayor, Max the third. I'm not joking. You can go downtown on the weekends and actually meet the mayor and his staff of deputy golden retrievers. And when we got back to the cabin, we had this private hot tub all to ourselves under the pine trees and enjoyed a private sunset view of the mountains.

0:56.6

It was so romantic and cozy.

0:59.6

It felt like our own private sanctuary and it made the trip just so special.

1:03.7

I'm glad he found that cabin.

1:05.2

When you book a stay on Airbnb, you find these absolute gems that are so much more spacious and have so much more personality.

1:12.4

It really elevates any trip into a memorable one.

1:15.5

Give it a try yourself.

1:16.7

The next time you travel,

1:17.7

try booking your next day on Airbnb.

1:34.2

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. Oh, baby, welcome to another episode of Why Won't You Date Me a podcast, or me Nicole Byer was trying to figure out why I was so single, even though you could come on a keychain ring and say, that's a lobooboo.

1:55.8

My guest today is a drag queen who competed on RuPaul's Drag Race Season 14.

2:01.1

I saw her backstage at Fat Slut,

2:04.3

a fun party where people dance sexy and eat food.

2:07.7

And I said, bitch, come on my podcast, because I was very drunk.

2:11.2

But I'm so happy she's here and I follow through with booking her.

2:15.0

It's June Jambalaya.

2:21.5

Hi, hi, hi, hi, hi, hi, hi. This is a dating podcast.

...

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