Minisode: Our Parents are Dating with Chelsea + Catherine

Summary

DEAR CHELSEA Minisode: Our Parents are Dating with Chelsea + Catherine
iHeartPodcasts | April 24, 2026

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Episode Overview

In this lively and candid minisode, comedian Chelsea Handler and her co-host Catherine Law tackle one of their most entertaining and complex listener questions yet: what do you do when your parents start dating each other? Against the familiar backdrop of friend-to-friend banter and advice tinged with humor and honesty, the pair explores family boundaries, blending households, and the awkwardness that ensues when your parent and your partner’s parent become romantically involved. Along the way, they also revisit updates from past callers and answer a sex and relationships question sent in by another listener.

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Key Discussion Points & Insights

1. Friendly Banter & Setting the Scene (05:37 – 07:44)

• Chelsea and Catherine open the show with casual, playful banter at Chelsea's home, highlighting their chemistry and authenticity.
• Notable quote:
  • Chelsea: "A real friend will be like, you have smoothie in your teeth." (06:17)
• The pair swap stories about sharing space with comedian Yamanika Saunders during Chelsea's tour, setting a relatable, warm tone.

2. Listener Update: "I Chickened Out" (07:50 – 09:56)

• Catherine brings in an update from Stephanie, a previous caller who had a crush on her boss (originally featured in the Josh Radnor episode).
  • Stephanie admits nothing romantic happened with her boss: he became less flirty after quitting drinking, started dating someone else, and now only occasionally texts her.
  • Chelsea quickly nails the subtext:
    • "Also, when somebody texts you at 12:30 in the morning, we all know what that means." (09:56)
• Both hosts agree Stephanie dodged drama and that continuing to flirt with her boss is probably not wise.

3. The Main Question: Our Parents Are Dating! (13:24 – 22:48)

The Situation (13:24 – 15:45)

• Listener Natalie writes in about her (and boyfriend Miles’) unique scenario:
  • Both Natalie’s dad and Miles’s mom lost their partners recently.
  • After a Thanksgiving invite brought them together, the parents have begun going on “old people dates” (antiquing, museums, etc.).
  • Natalie and her sister tease their dad affectionately, but Miles finds the situation “awkward and weird,” and is less comfortable.
  • Communication styles differ: Natalie is open with her dad, while Miles’s mom isn’t sharing as much, intensifying Miles’ discomfort.

The Live Call (15:45 – 22:48)

• Chelsea brings Miles and Natalie on for a live discussion.

  • Chelsea’s Immediate Take (16:08):

    • "Luckily, it’s really not either one of your business... Let them do their thing. They're happy. What are you gonna do about it?"

  • Miles explains his discomfort stems from:

    • How quickly the relationship started after loss (trauma bonding)
    • His mom not being open with him about it
    • Concern for his children, who recently lost their grandfather

  • Chelsea reframes the situation:

    • "We want people to be happy, period, don't we?...Who cares if it was two weeks? At least they have each other to, like, console and confide in and spend time together." (18:33)
    • She notes it’s reasonable to protect the kids’ feelings and suggests boundaries.
    • Advice: Present a united front to the parents, express acceptance, but ask for discretion and sensitivity about how quickly the relationship is revealed to their kids.
    • "All you can do is throw love and support their way. That's it. You're not here to judge them...just here to support."

  • Memorable Moments:

    • Jokes about double dating and role play.
      • Miles: “If they get married, then me and Natalie will be step—like, I’m like, no, we’re not doing that kind of role playing.” (22:09)
    • Chelsea, reframing everything with humor:
      • “Take it for what it is. It’s pretty fucking entertaining…Just look at it through the lens of comedy and entertainment. Everyone...could use a laugh right now.” (22:20)

4. Recap and Reflection (26:19 – 26:54)

• Chelsea and Catherine reflect on the "parents dating" question.
  • Chelsea: "I just love that when people die...the old people just, like, cling on—or, they fast. Everything is quick because they have been through life and they're like, ‘Fuck this waiting.’" (26:22)

5. Quick Advice Segment: "Closet Power Bottom Needs Your Help" (27:15 – 30:14)

• Listener Charlie, a gay man in LA, asks whether it's worth taking on medical debt for a specialist to remove a recurring and painful skin tag affecting his sex life.
• Chelsea’s advice: Invest in your own pleasure if you can afford it, especially for something that blocks joy.
  • "I would say financially, just to take a bullet and do it." (29:48)
• Catherine adds: "Especially if you can pay it off over time." (29:51)
• The pair reinforce sex-positive messages and self-acceptance.

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Notable Quotes & Moments (with Timestamps)

• Chelsea on friendship honesty:
  • "A real friend will be like, you have smoothie in your teeth." (06:17)
• Chelsea on giving embarrassing news:
  • "It's more uncomfortable for the teller than the telly." (08:09)
• Stephanie’s update:
  • “He did randomly invite me to watch his favorite movie. Then the next day, he told me he met someone. I'm not hurt by it...I’d for sure still like to make out with him at least once.” (09:14)
• Chelsea on “You up?” texts:
  • "Also, when somebody texts you at 12:30 in the morning, we all know what that means." (09:56)
• On parental romance boundaries:
  • Chelsea: "You're not here to judge them, you're not here to guide them. You're just here to support them." (21:49)
  • On seeing it with humor:
    • "Take it for what it is. It's pretty fucking entertaining." (22:20)
• Charlie’s question on medical bills for sexual enjoyment:
  • Chelsea: “I would say financially, just to take a bullet and do it.” (29:48)

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Important Segments & Timestamps

• [05:37] - Chelsea & Catherine’s casual catch-up and home setting
• [07:50] - Stephanie’s update: “I chickened out”
• [13:24] - Listener letter: “Our Parents are Dating”
• [15:45] - Live call with Natalie and Miles about their parents’ relationship
• [22:09] - Jokes about new step-sibling status and comic relief
• [26:19] - Reflection on the question and older people dating
• [27:15] - Question: “Closet Power Bottom Needs Your Help”
• [29:48] - Chelsea advocates for investing in personal pleasure

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Tone & Language

• The conversation is informal, humorous, honest, and sex-positive, peppered with explicit language and plenty of mutual teasing.
• Chelsea is blunt and witty but empathetic, always steering guests toward self-acceptance, boundaries, and seeing the comedy in awkward situations.
• Catherine plays the supportive confidante, offering gentle reality checks and laughs.

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Takeaway

This episode of Dear Chelsea blends laugh-out-loud moments, heartfelt advice, and refreshingly candid takes on family, sex, and navigating the absurdities of modern life. The "parents are dating" dilemma is treated with equal parts sensitivity and comic relief, with Chelsea always leading with the reminder: happiness, boundaries, and humor are key—no matter how weird life gets.

Transcript

[A]

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[B]

April 23 is Kansas City, Missouri. April 24 is St. Louis, Missouri. April 25 is Minneapolis. April 30 Nashville.

[A]

May 1, Charlotte, North Carolina.

[B]

May 2 is Durham, North Carolina. May 6 in Los Angeles at the

[A]

Saban Theater for Netflix is a joke.

[B]

May 15th I will be in Saratoga. May 16th, Monterey. May 17th Modesto. I will be in Port Chester on June 4th.

[A]

And we added two new dates to the High and Mighty Tour. On June 3rd I am coming to Saratoga Springs, New York City. So pre sale has begun for that. And then on June 28th I am coming to Nantucket.

[B]

And pre sale has started on that. June 5th I will be in Boston, Massachusetts. June 12th, I will be in Portland, Oregon.

[A]

And June 13th I will be in Seattle, Washington. June 27th it's going to be Hyannis, Massachusetts.

[B]

August 6th is Red Bank, New Jersey. August 7th I'm coming home to Montclair, New Jersey.

[A]

August 15th is Calgary, Alberta, Canada.

[B]

September 18th, Santa Barbara. September 19th, San Diego.

[A]

September 25th I will be at the

[B]

Beacon in New York City. September 26, I will be in Philadelphia. September 27, New Haven, Connecticut. October 2, Atlanta, Georgia. October 3, Baltimore, Maryland. October 4, Saginaw, Michigan. October 9, Pittsburgh, Pennsylvania. October 10, Toronto, Canada. October 16, I'm coming to Boise, Idaho.

[C]

October.

[A]

October 17, Spokane, Washington.

[B]

November 7, I will be in San Francisco. And November 13, Salt Lake City. November 20, Austin. November 21, Houston, Texas.

[A]

November 22, Irving, Texas.

[B]

December 5, I am adding a second

[A]

show in Denver for those of you

[B]

who couldn't get tickets to the first one. And on December 6th, I will be

[A]

coming to Vancouver, Canada. Okay, those are all my dates for

[B]

the High and Mighty Door.

[A]

Go to Chelsea handler.com for tickets. Hi there. Hi, Katherine.

[D]

Good morning, Chelsea.

[A]

Good morning. Hi.

[D]

We're back in your house.

[A]

My house is trying to be. We wouldn't lit a candle. Look, guys, we're in my home. It's nice. I slept at about 13 hours last night.

[D]

I love it.

[A]

Incredible. Se siento incre or siento incredible?

[D]

Yeah, siento incredible.

[A]

Yes. You have something in your tooth right there to the left of your. To the left of your big tooth.

[D]

This one?

[A]

Yeah.

[D]

Do I get it?

[A]

No, it's right. That one. Brad, I think it's gone. No, that should be on camera for sure. Yeah, it's gone now.

[D]

I mean, listen, I do think, like a real friend will be like, you have smoothie in your teeth. Which is exactly what's going on there.

[A]

Yeah, you have to tell people. I don't even think it's about being a friend. It's just about seeing it's respect.

[D]

It's like it's more embarrassing for the person in the moment. But then not think about that.

[A]

No, I mean, I want someone to tell me when I have fucking food in my tooth. Or teeth. Or a tooth.

[D]

I was actually talking to Yamaneika's folks yesterday.

[B]

She's got.

[A]

Yamanika's moving in, you guys.

[D]

She is.

[A]

I let her sleep with me one night on the road. Cause she fucked up and double booked herself into two hotel rooms in the wrong city. So we were like, say we were in Chicago. She booked them in Minneapolis. Two hotel rooms. So she lost all that money. And so I let her sleep with me one night. Then the next night she's like, that was fun. I was like, it was fun. Cause it was one night. It's not fun for you to be fucking sleeping in my bedroom with me two nights in a row. So. So then now she's sleeping here. For Netflix is a joke festival. We'll both be performing, you guys. May 6th. Tickets are available at Chelsea. ChelseaHandler Jam, Chelsea handler Jam. And she'll be staying here. And then I fear she'll never Stay anywhere else.

[D]

I don't think she's gonna leave, quite frankly.

[A]

I just got a text from her. We're doing shows this weekend, and she said, oh, I fucked up with my hotel room in Mesa, Arizona.

[D]

And I was like, that's on purpose.

[A]

At this point, I know she wants to be with me. And we've discovered that she'll take sex from a man or a woman. So she's fluid. She's not. She doesn't care. She just wants action. And I think she gets so much affection from me that she's confusing that with some sort of sex.

[D]

You don't have Doug there, so you just have to, like, cuddle. Yamaneka.

[A]

Yeah. Well, that's racist. Katherine.

[D]

I have an update from caller and this is a little bit of a disappointing one.

[A]

They took my advice and all. Shit went wrong.

[D]

No, she chickened out. So Stephanie, who had called in on our Josh Radner episode, the one who wanted to make out with her boss,

[A]

I just have to tell you now, the thing that was on the left side of your tooth is on the right side of your tooth.

[D]

Do you have a toothbrush? I gotta.

[A]

And I wanna just be on the record. It's more uncomfortable for the telly.

[D]

It is.

[A]

It is for the teller. For the teller than the telly. Because then you have to bring it

[D]

up twice, especially when it moves.

[A]

And it can sound like you're kind of like, you know, like. What's the word? You're like a bitch.

[B]

Yeah.

[A]

Yeah. Or like you're trying to make someone feel bad and I'm.

[D]

Thank goodness Chelsea likes you, Brad.

[A]

You think that's the first time I've been called a bitch?

[D]

Yeah.

[A]

You're fine now. There you go. You did it.

[D]

You did it.

[A]

Let me know if it's a team, okay?

[D]

So Stephanie says hi, Chelsea. Well, I probably still have a crush on my boss. Nothing ever happened after I talked to y'. All. He left on a work trip for a couple weeks, then returned, only to leave for more travel about every four to five days. This allowed me to reflect as it was all quite literally making me go crazy. I think she was just maybe very horny at the moment. He had stopped drinking, and this actually changed our dynamic a ton. Not as much flirting or texting. We stopped going to dinners or events. He did randomly invite me to go watch his favorite movie. Then the next day, he told me he met someone. I'm not hurt by it. This is his third girlfriend in nine months. He texted me last night at 12:38am saying he liked my new hairstyle. WTF? I know. He's like dragging her along.

[A]

He's annoying.

[D]

Yeah, yeah. Anyway, he loves very hard and honestly, I'm not interested in love bombing. I'm too independent for that. So there's a little relief. It's not me. Also, I still love my job and I don't want to leave it to even explore this option. I'd for sure still like to make out with him at least once. I mean, why not? But for now, it's boundaries and being a supportive friend slash co worker. Stephanie.

[A]

Great.

[D]

That worked out for a little bit.

[A]

That's probably best. She probably saved herself. Yeah, some like drama and whatever other words go with drama.

[D]

Yeah, love bombing for sure.

[A]

Yeah, yeah, yeah. Also, when somebody texts you at 12:30 in the morning, we all know what that means.

[D]

We all know what that means. That means. You up?

[A]

Yeah.

[B]

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[D]

Okay, it's time for some couples counseling with Chelsea. So this is Miles.

[A]

I'm having a lot of heat, by the way, for my couples.

[D]

Oh, good, you're dating.

[A]

Yeah, a lot of heat between gay guys and gay girls. Gay girls and gay girls are gay girls. And a lot of heat between gay guys. But we're still having problems personally before I put the men up because I didn't really want to put women up and just have men like they're just. Men are not to be trusted. So. But I did do some finagling on the side before I started broadcasting people. And there's like two people that are on straight couple that are on their like third and one is on their fourth date.

[D]

Well, do you know if you. You probably do know this if you introduce three couples who get Married. It's like a mitzvah or you're a mensch, something very good.

[A]

Well, that's all right. That's already a mitzvah and I'm a mensch. I don't need. I need that. And I thought you were going to say I'm become a fairy or something.

[D]

You're going straight to heaven.

[A]

Oh, well, I wish I believed in that.

[D]

Well, Miles and Natalie. This is Natalie writing in. She says, dear Chelsea, My boyfriend and I recently moved in together and blended our families. We've been together almost three years and have had no major issues until now. Recently, my dad lost his partner and his mom lost hers. This past summer. We invited both of them to join us. This past Thanksgiving, so they weren't alone. A few weeks ago, my boyfriend's mom reached out to me for my dad's number. All I thought was how nice a friendship is blossoming. I'm getting texts from my dad with pictures of them gallivanting around little small towns in the Midwest, antiquing, meeting for coffee, drinking wine and going to museums. All things you would expect old people dates to look like. My boyfriend doesn't like this whatsoever. It's nothing personal toward my dad, but he thinks it's selfish of them to do this to us. My sister and I, however, find it awkward and weird, but think it's actually kind of funny. We're very close with our dad since we lost our mom unexpectedly five years ago. We have the type of relationship where my sister and I call him a hoe bag and tease him about all of this. It is weird, but we're supportive. My boyfriend and his mom are not quite as close. They haven't communicated much about this at all. Since she knows he's not supportive. Here's the thing. I normally tell my boyfriend everything. I want to be able to come home and laugh that his mom spent the night at my dad's, that they went to a museum today. Etc. He gets pretty weird about it. I totally understand his viewpoint, but you only live once and it really doesn't affect our life, is what I say. Help. Miles and Natalie.

[A]

Hi, Miles and Natalie.

[D]

Oh, hi.

[A]

Hi.

[E]

How's it going?

[A]

Good. How are you two doing?

[E]

Good.

[A]

So your parents are hooking up?

[E]

Yes.

[C]

Yes.

[A]

And Miles?

[C]

You don't like that I'm not a fan? No, not at all.

[E]

And I'm a little bit more on the supportive side.

[A]

Right. Well, luckily it's really not either one of your business. You know what I mean? Like, it's really not up to you. Guys what your parents are going to get up to. And while I understand you're disconnected. Comfort, Miles, I can relate. I just think that, like, let. They've got to do their thing and they're happy and, you know, like, what are you gonna do about it?

[D]

I think it's so cute.

[A]

It is cute, but I understand the reluctance in wanting to know the details. And Natalie, you don't have to tell Miles everything you know about their relationship. Like, it's on. If he's interested, he'll let you know. And other than that, you've got to just kind of like, have a great, nice, loving attitude towards them for doing their thing. It's not like they're having sex in front of you and you have to sit there and watch it. Like it's not. That's not happening. So be grateful for small blessings.

[E]

Yep. Yep.

[D]

So, Miles, is it just the ick factor or is there anything else?

[C]

No.

[D]

That you're.

[C]

No, it's not even that. I. I think it's how it happened. Not that it happened, if that makes sense, because they both recently lost somebody very, very within a couple weeks of each other. He lost his significant other, my mom lost her significant other. And so they. It's kind of like trauma bonding, which has then evolved into something else. And. And also, she was not honest about it, where he was telling Natalie everything that was going on, and my mom was not telling me anything that was going on and not being honest about it, even when I asked her about it. So I think that's where.

[E]

But then he also came across like that he wasn't as supportive. So then I was like, well, why is she gonna wanna tell you anything?

[A]

Yeah, I mean, first of all, Myles, you're like, kind of like setting her up for failure because she obviously consents. As your mother and as a woman, we all have intuition. She can sense that there's a level of disapproval coming from you, whether or not you're exhibiting that or not. Like, a mother will know how her son feels about something, especially her personal life and especially, like, this kind of sensitive issue. But something that's really important to remember is, like, listen, we want people to be happy, period, don't we? We want the people in our lives to be happy. Don't make excuses for why you should be unhappy for them or you should be unsupportive of them. Be happy that they found each other. Who cares if it was two weeks? At least they have each other to, like, console and confide in and spend time together. And isn't that what you would want for any single person in your life that you cared about?

[C]

Yes, I would agree with that.

[D]

Do you think they should like address this with mom and dad or that he should with mom just be like,

[E]

I'm happy for you or it's already been addressed.

[D]

Okay.

[E]

And one awkward thing that I got in the middle of is they both called me and had me on speaker because my dad wanted to go to his kids sporting event that his mom was going to. And I'm like, why would you be going to that? Like, I'm not even gonna be there.

[C]

And so we haven't told the kids.

[B]

We haven't told the kids none of the grandkids.

[C]

No.

[E]

And so they didn't. Why. That's socially awkward. And you know why Miles is having an issue with it. And then I was just like, you

[C]

know, so my, my kids were pretty attached to their grandpa. That just passed. So introducing us so quickly. So that's another aspect of this is that I don't, it's not that I don't want her to be happy, but my kids, it. He passed from a long hard disease and so it was long deterioration of watching this and then all of a sudden they're at his funeral and then all of a sudden this is going on. So we have not broken this to, to the kids yet.

[A]

Okay. How old are your kids?

[C]

Mine are 10 and 12.

[E]

Minor 7 and 9.

[A]

Okay. Wow. Good for you guys.

[D]

That's nice.

[A]

Yeah, yeah.

[E]

Half the time, so.

[A]

Yeah. Well, even better. That's reasonable. That's totally reasonable. Not to want to introduce this relationship to your children. That's a separate issue. So like, while you work on your acceptance, you guys can both have like a conversation with them and, and I would do it together just to make sure they know you're a united front so they're not playing you off of each other like children would do because you know what I mean, like let them know you guys both are supportive. And Myles, you can use this as an opportunity to be like, yeah, we're supportive. We want you both to be happy. The timing is a little quick. While we're going, we are in full acceptance mode and working on our acceptance. We do have to take some time to be sensitive to the children and what they are learning. And you guys coming out as a couple so soon after doesn't feel right. So let's give it some time. And we just want to make sure you guys understand where we're coming from and that you can be respectful of that and that's not a tall order.

[E]

Yeah, yeah. They did come over for Easter and we told them like, that's fine. Just arrive separately and no flirting.

[A]

Right.

[D]

They're best friends with their kids.

[A]

Friends. Well, so then they can, they can follow the program. Right. If you set the rules down for interaction and you only have the right to set rules around your family and your children, that's it. You can't direct them in any other way. Even if this blows up and ends up being a real like dramatic something like breakup or whatever, like all you can do is throw love and support their way. That's it. You're not here to judge them, you're not here to guide them. You're just here to support them.

[E]

Okay.

[B]

Yeah, yeah.

[D]

And now you can double date.

[A]

Yeah. So that's. So just.

[E]

Yeah.

[A]

Just make sure that they know that they have to leave their clothes on at all times.

[E]

I know.

[A]

Especially around family members.

[D]

Or maybe just like not kiss in front of you two for now.

[C]

My friends recently made a joke that, well, if they get married, then we'll be step. Me and Natalie will be stepped. Like, I'm like, no, we're not doing that kind of role playing. Nothing. No.

[A]

I mean, listen, take it for what it is. It's pretty fucking entertaining.

[D]

It is pretty entertaining.

[A]

You know what I mean?

[D]

Yeah.

[A]

So look at it like that through the lens of comedy and entertainment. Everyone could probably, on both sides could use a laugh right now. So Let that Be

[E]

is pretty hilarious. Which is. Yeah, I thought it was a good topic for your show.

[A]

Thank you. Yes, it's perfect. We love it.

[D]

Thank you.

[A]

More of this, please. All right, you guys take care.

[C]

All right, bye. Thank you.

[A]

Listen, I have access to a lot of things that most people don't. Top dermatologists, high end treatments.

[B]

But in those circles, the conversation has shifted. Now it's about extending youthful looking skin before invasive options. That's why people in the industry are talking about exosomes. Exosomes are disrupting the beauty world and plated skin science is leading the conversation. Plated has elite award winning technology and over 10 clinical studies with remarkable results. Clinically proven to deliver brighter, firmer, younger looking skin in just weeks. This is more than skin care. It's a cosmetic treatment in a bottle. Visit plated skinscience.com for business owners and

[A]

entrepreneurs, there is a constant challenge getting things done fast and done well. Why not have both? That's why wix Harmony stands out. It's an AI website builder that helps create a website quickly without compromising your vision. A fully functional site can be built for any business just by describing the ide. Then you can choose to chat with AI or edit everything manually to get it exactly right. There's also Aria, an AI agent available to answer questions or help complete tasks. And here's what makes it even better. Aria doesn't just live in a chat box. You can click anywhere on your site and ask her to make changes instantly. It's these details that make creating with Wix Harmony feel seamless. Join millions of businesses already using Wix and try Wix Harmony with for free at wix.com harmony that's wix.com harmony when it's time to Get a New Car, where do you start? Car shopping can be, honestly, a little overwhelming, but it should be fun. Buying your next car should be exciting. And it can be. And if you can remember one thing, it's cars.com My dad was a used car salesman, so I know way more than I want to about the car buying process. And that means I also know how to get a good deal. And that's also why I'm uniquely qualified to tell you how easy it is to find the Perfect car on Cars.com Cars.com has the tools and expert advice to help you figure out what vehicle is right for you. Their site is super easy to use, and their advanced search filters allow you to filter over 2 million new and used cars to find the exact car that you're looking for. Every review is written by a real person, reflecting a real life experience. That's how you know you can trust the dealerships on cars.com cars.com features transparent deal ratings, including tools and badges to help shoppers understand the price of a vehicle and find the best deal. Finding a good deal is pretty important, and by understanding how a car's price compares to others in the area, Cars.com will help seal the deal. So don't take any chances. Do car shopping the easy way. Start your search with cars.com where to next? You're probably hearing a lot about longevity right now. I know I am. And I know I care about it. And when it comes to skin, aging is linked with a decline in cellular energy. As that energy decreases, skin doesn't regenerate or renew itself as efficiently. And that's when you start to see dullness, fine lines, and loss of firmness. Obagi Medical has been trusted by dermatologists for over 35 years. Their newly launched facial serum, New Gen Cellular Renewal Serum, is powered by NAD and supports skin's natural renewal Processes at the skin cell level. In clinical testing, skin appeared up to six years younger after 12 weeks. Learn [e-mail] and new customers can use code Chelsea15 for 15% off qualifying orders. Terms apply.

[D]

That's maybe one of my favorite questions we've gotten in a while.

[A]

I just love that when older, when people die, like the old, people just like cling on. Not cling on or they fast. Everything is quick because they have been through life and they're like, fuck this waiting. It's like the opposite of girls not knowing whether to call a guy or approach a guy. It's like they know there's no time to lose and that they got to get down to business.

[D]

Especially if they just lost somebody. Like, they're like, let's make it happen. I like you, you like me.

[A]

Let's. Right, right. That guy's dead. He took him a long time to go. There was no sex, probably, you know.

[D]

Right, right, right. Okay. Well, speaking of sex, we have our.

[A]

You want me to have sex?

[D]

Don't make me blush.

[A]

Chelsea.

[D]

Sorry.

[A]

I'm sorry for hitting on you.

[D]

We'll leave you in the top half.

[A]

That's a definite no.

[D]

No, no, no, no.

[A]

I mean, it's. That's why I can't have a real job, because I would be fucking evicted from it. Evicted. Notice my use of eviction.

[D]

That's what they do at jobs when you can't be there anymore. So this question is our wondering question of the day. And the title is Closet power bottom needs your help.

[A]

Dear Chelsea, I believe I'm a power bottom. Yeah, I like to be on bottom.

[E]

I.

[A]

Sometimes being on top is too much work.

[D]

Agreed. Like, you.

[A]

Fucking work. You're getting to fuck me. Fuck me.

[D]

Men have more muscle. Quote, unquote. Use it.

[A]

Yeah, I don't understand, like, I want to just get fucked up.

[D]

Have you seen this thing online that's like men planking till failure and how can they last? I think it's less about that than just like hearing them struggle and being in a playing position.

[A]

No, I feel. Yeah, I'm. Yeah, I want to get on top of you. I'll let you know. Yeah, I'll tap you out.

[D]

So Charlie says, dear Chelsea, I'm a 27 year old gay man living in Los Angeles with a little bit of an odd situation that I need you to weigh in on. I developed a large skin tag on my butthole when I was around 21. As you can imagine, this would interfere with my sex life. I finally had it removed when I was around 23 after the removal. Sex was amazing. I could finally bottom and I was really enjoying it. Everything was good for about a year or so, and then it started to grow back. This time bigger and more painful. Oh, I know. Now I'm single and in the best shape of my life. I'm a true verse, but I absolutely love bottoming, which I feel like is like the secret of a lot of people who say their verse is like, they really love to be a bottom.

[A]

Oh, is that right?

[D]

Yeah, I think that's like.

[A]

I wouldn't.

[D]

Unfortunately, because of the skin tag, I've become a strict top. It.

[A]

Does it hurt to have sex with the buttons?

[D]

Yeah, I think it's like, because of this, it's like getting in the way. I found a doctor who specializes in gay men, but it's quite expensive and insurance won't cover any of the cost.

[A]

To do what? Remove it again.

[D]

And I guess like the last person, the last doctor was not a gay men specializing doctor and like, could have been done better. I live comfortably, but this is something I would have to take on some medical debt for. Is it worth it? Part of me thinks that's irresponsible, but I also want to fully enjoy my sex life as a single man. P.S. i was at the Netflix as a joke show at the YouTube Theater. I'm a big fan of Chelsea's, and that was my favorite comedy show I have ever been to, sincerely.

[A]

Well, you can come again. Netflix is a joke. Festival starts again May 6th. I'm at the Sabaam theater this year. Okay. Yes, you should. But why doesn't insurance cover this? And maybe that's a stupid question. Because he's a gay man and they know they're.

[D]

It's a specialist, so it's like not under his insurance.

[A]

Okay, so it's not under his insurance. I would say it's worth the investment. I think if something you enjoy. Yeah, yeah. That you're being. You're being. You're prevented from doing because of that. And it's removable.

[D]

Yeah.

[A]

I would say financially, just to take a bullet and do it.

[D]

Yeah. Especially if you're like living comfortably and like you can pay it off over time.

[A]

And also to find out, like, how to get rid of it. Is there a way to get rid of it so that it doesn't come. Is there a way to ensure that it doesn't come back? Back.

[D]

Right. I mean.

[A]

No, maybe there isn't.

[D]

Yeah, maybe there isn't. But also the specialist would probably be the one to be able to answer that.

[A]

So yeah, yeah, I want people to be enjoying themselves.

[B]

Right.

[D]

Exactly. Like I think. I think it's definitely worth it.

[A]

Yeah.

[D]

Okay.

[A]

Well, we'll see you guys next week.

[D]

Bye.

[A]

Adios.

[D]

If you want advice from Chelsea, write in to dearchelsea podcast gmail.com Dear Chelsea is a production of iHeartMedia. Follow Chelsea on all socials and at Chelsea Handler and find Katherine on TikTok Flash Cadabra. Dear Chelsea is edited and engineered by Brandon Dickert, Executive Producer Katherine Law. Find full video episodes and minisodes now on Netflix and get tickets to see Chelsea live@chelsea handler.com.

[B]

Listen I have access to the top dermatologists, high end treatments, beauty experts, all of it. But what's interesting in those circles is that the conversation has shifted. Now the talk is about extending the longevity of youthful looks way before more invasive options and the latest science from the Mayo Clinic Proceedings plus Stanford University not only do we know now that visible aging happens in bursts one day, you look and feel like yourself on the next. Well, no. But we also know that the way our skin looks is a mirror to our overall wellness. That's why people in the industry are talking about Exosomes as the most innovative solution to younger, firmer looking skin. Plated is one of the brands that really stands out. Their Exosome technology has won countless beauty awards as well as innovation awards including Time Best Invention. Plated has over 10 peer reviewed clinical studies data showing remarkable results on real people in just weeks. Plated is clinically proven to reduce the visible signs of aging and deliver younger, brighter and firmer looking skin. This is more than skin care, it's a cosmetic treatment in a bottle. Visit platedskinscience.com a doubly certified OB GYN

[F]

and endocrinologist doctor, a naturopathic doctor and a certified health coach walk into a room. What do they talk about? GLP1 of course, but more specifically the difference between the synthetic version of your body's own hormone that are prescribed by doctors nationwide versus metabolism ignite product which naturally naturally increases your body's GLP1 by 61% GLP1 side effects can lead to nausea, fatigue and muscle loss, whereas metabolism Ignite is powered by plants and there are no side effects. Some long term results of GLP1 links to weight gain after stopping the synthetic drug which has been proven in multiple studies. In comparison to Metabolism Ignite there is no weight regain and this product supports metabolic health. Join the 50,000 customers by skipping the needles and taking two capsules of metabolism ignite a day. For sustained weight loss with plant based therapy, visit V E R A C I T Y Health co. Promo code IHEART for up to 65% off your order today.

[A]

It's 2026. We upgraded our phones, our cars, even our coffee. So why are we still acting like pleasure is negotiable at Pinkcherry? It's not. They've got hundreds of toys that actually deliver, and if you don't know where to start, their mystery boxes make it easy. Go to pinkcherry.com and use promo code Chelsea to save up to 80% sitewide because life is hard. Feeling good shouldn't be pinkcherry.com because everyone deserves pleasure.

[G]

You're probably hearing a lot about longevity right now. And when it comes to skin, aging is associated with a decline in cellular energy. As that energy decreases, skin doesn't regenerate or renew itself as effectively, which is why you start to see dullness, fine lines, and loss of firmness. Obagi Medical has been trusted by dermatologists for over 35 years. Their new gen Cellular Renewal Serum is powered by NAD and supports SKIN's natural renewal process. In clinical testing, skin appeared up to six years younger after 12 weeks. Learn [e-mail] and new customers can use code TPOD15 for 15% off qualifying orders. Terms apply.

[A]

This is an iHeart podcast. Guaranteed Human.