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Dear Chelsea

Jersey Girls with Debbie Gibson

Dear Chelsea

iHeartPodcasts

Comedy, Education, Self-improvement

4.43.6K Ratings

🗓️ 11 September 2025

⏱️ 64 minutes

🧾️ Download transcript

Summary

Debbie Gibson joins Chelsea in-studio to talk about the one that got away, when teenage girls know more than men in suits, and what life is like in her second act. Then: Menopause has a divorcee feeling down.  A 30-something and her bestie beef with judgmental parents.  And a grieving daughter wants to get her life back. 

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Need some advice from Chelsea? Email us at [email protected]

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Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

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The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opinions of iHeartMedia or its employees.  This Podcast should not be used as medical advice, mental health advice, mental health counseling or therapy, or as imparting any health care recommendations at all.  Individuals are advised to seek independent medical, counseling advice and/or therapy from a competent health care professional with respect to any medical condition, mental health issues, health inquiry or matter, including matters discussed on this Podcast. Guests and listeners should not rely on matters discussed in the Podcast and shall not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice. 

See omnystudio.com/listener for privacy information.

Transcript

Click on a timestamp to play from that location

0:00.0

This is an IHeart podcast.

0:04.2

I just normally do straight stand-up, but this is a bit different.

0:08.0

What do you get when a true crime producer walks into a comedy club?

0:12.2

Answer, a new podcast called Wisecrack, where a comedian finds himself at the center of a chilling true crime story.

0:18.8

Does anyone know what show they've come to see? It's a story.

0:23.3

It's about the scariest night of my life. This is Wisecrack, available now. Listen to Wisecrack on the

0:30.4

IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hi. Hi, Chelsea. Hi, how are you?

0:37.9

I'm great.

0:38.7

You just got back from New York. I was at the U.S. Open. I had to go to the women's finals. It was mandatory. I had to see that final match between Anna Samova and Sabaanka. Okay, so what do you like about being there? Is it the sports? Is it the sort of CNBCN? seen, it seems like a very sort of like celebrity event. Yeah. It is more celebrity here at the U.S. Open than it is at like the other grand slams, I think. There's always celebs, but at this one is definitely like a New York thing. So I've never been in the Australian Open. I've never been in the French Open. I go to Wimbledon every year for a few matches whenever I can get there, the beginning or the end. Obviously, it's better to get there than end because it becomes more competitive. But the U.S. Open just has the most fun vibe. Really? Okay. First of all, it's like, it's so fun because I know a lot of tennis people.

1:28.8

So I, whoever invites me, like you could go as a, you could buy your own ticket or you could go as a guest to like one of the brands there or like I went and sat in the president's box for this match

1:34.0

since I was invited by somebody there. And then it's just like a fun vibe. A, they're drinking. They

1:40.9

have honey deuses. Like every open has their signature drink. Like Wimbledon, it's Pims cups, which are so fun. And Wimbledon is very, very convivial and beautiful, but a little stiffer. You know, you've got to be a little bit, a little bit more proper. I mean, I'm not, but that's what they're expecting. And then U.S. Open is just kind of like more loosey-goose. Like it's just a really

2:01.8

relaxed vibe. It's a fun day out. I went with two of my friends, Naomi and Serena this time. I mean, I went with Hannah Berner in one of the matches. I went with Juliana Margulies to one of the matches. But then I was it. I was like, okay, you know what? I have to go back for the finals. So I flew in for literally the day to go watch the finals in person. But it's just the

2:21.2

atmosphere. The atmosphere is

2:22.9

just bubbling and I love that vibe. I'm a day person. I love that like day atmosphere.

2:29.3

And then, yeah, and then you're home at a reasonable hour. And yeah, I don't know.

2:33.8

Yeah. See, if you're ever going to catch me at a reasonable hour. And, yeah, I don't know. Yeah.

2:53.3

See, if you're ever going to catch me at a sports match of any kind, it's something that has a fun crowd. You know, like, I'm not there. I don't know who's playing. I don't know who's winning. But, like, I in high school spent some time in Mexico, and we would go to the baseball games there. And they would like light rolls of paper towels on fire and like throw them down the stands.

3:11.5

Like it was a very crazy, fun environment. So, like, I'm not there to check out the sports, but, like, I love a dodger game. As you can see, see, I neglect you to mention any of the tennis. But what I do love about the tennis is that it's a level of excellence. You know, like, if you watch the Benz, it's the same guys that get past that knock everybody out of the way.

3:12.3

It's the same three guys. It's Djokovic, it's Jokovic, it's Yonik Sinner, and it's Alcarez. They knock everybody out of their way. So they are playing at such a high level. So, and with the girls, they're less,

3:21.9

Arena Sabalanka is very consistent.

3:23.8

She's always in the finals,

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