Dear Chelsea - Minisode: Type Ho Positive with Chelsea + Catherine

Episode Date: November 28, 2025

Chelsea and Catherine get an update from a caller whose bestie is about to be barefoot and pregnant. Then: A boyfriend struggles with asking his partner to open things up.  * Need some advice from Chelsea? Email us at [e-mail] * Executive Producer Catherine Law Edited & Engineered by Brad Dickert * * * 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.

This is an I-Heart podcast. Guaranteed Human. I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money. And now we're back making this new podcast called Business History, about the best ideas and people and businesses in history. And some of the worst people, horrible ideas, and destructive companies in the history of business.

First episode, how Southwest Airlines use cheap seats and free whiskey to fight its way into the airline is. The most Texas story ever. Listen to Business History on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey there, Dr. Jesse Mills here. I'm the director of the men's clinic at UCLA, and I want to tell you about my new podcast called The Mail Room. And I'm Jordan, the show's producer. And like most guys, I haven't been to the doctor in way too long.

I'll be asking the questions we probably should be asking, but aren't. Every week, we're breaking down the world of men's health from testosterone and fitness to diets and fertility. We'll talk science without the jargon and get your real answers to the stuff you actually wonder about so check out the mailroom on the iHeart radio app apple podcasts or wherever you get your favorite shows podcasters it's time to get the recognition you deserve the iHeart podcast awards are coming back in 26 got a mic then you've got a shot every year we celebrate the most creative compelling and game-changing voices in podcasting is that you submit now at iHeartpodcastawards com for a chance to be honored on the biggest stage in the industry deadline december 7th

This is your chance. Let's celebrate the power of podcasting and your place in it. Enter now at iHeartPodcastawards.com. What up, y'all? It's your boy, Kevin on stage. I want to tell you about my new podcast called Not My Best Moment, where I talk to artists, athletes, entertainers, creators, friends, people I admire who had massive success about their massive failures.

What did they mess up on? What is their heartbreak? And what did they learn from it? I got judged horribly. The judges were like, you're trash. I don't know how you got on the show. Check out Not My Best Moment with me kept on stage on the I Heart Radio app, Apple Podcasts, YouTube, or wherever you get your podcast. On this week's episode of Next Chapter, I, TDJ, sit down with Denzel Washington, a two-time Academy Award-winning actor and cultural icon.

I don't take any credit for it. I just didn't put me first. I just put God first. and he's carrying me. Listen to the next chapter podcast on the I Heart Radio app, Apple Podcasts, or wherever you get your podcast. New episodes drop weekly. Hi, Catherine. Hi, Chelsea.

Hi. What are we doing? We're doing a minisode today. Today's welcome to our minisode. Yes, we have a follow-up actually from our Heather McMahon episode. This is Carly, and she had that friend who was dating sort of. like a maga yokel guy who wanted her barefoot and pregnant and was like already talking about the pre-nup. Do you remember this one? Yes, I do. It's amazing that I remember, but I do.

Once there's enough specifics, we remember. So she says, dear Chelsea, I wish I was writing in with a better update. My friends and I tried our best to get H to leave her boyfriend. We promised her that she wasn't stuck, that we were always there for her and that she didn't have to settle. This always came after she had a couple drinks and told us how unhappy she was with him. Well, despite all this, they got engaged last night. I kept it together during the phone call, but immediately broke down after. She's throwing her life away to move to Alabama, just to pop out babies for the rest of her life. I'm so sad for her. All that being said, I'm now on bridesmaid duty. No. How do I keep it together? No, no. Yes, you know the question. How am I

supposed to be happy for her. She's generally so happy and I want to be, but it just doesn't come naturally. Carly. I just think you have to say I can't support this marriage. Honestly, if someone like that who's basically telling her or not that she can't work, I mean, she's giving her life away to some man. And in this day and age, when you make a decision, when I make a decision, I consider all women. Like, I am making a decision on behalf of all women most often when it's something like related to men, or it's related to work, or it's related how I'm going to stand up for myself. It's always about what we do, what, you know, thinking about all the other women. And that's just ridiculous.

You're throwing yourself away. Yeah. Basically. In Alabama, no less, with a guy that doesn't think you're supposed to work for a living. So I would, I would, like if you know, there's any way to put your foot down, this is it. I mean, if there were any time, this is it. That I can't be, I'm so sorry.

I love you so much, but this is breaking my heart and I cannot be involved in this wedding. You are making the wrong decision right now. Yeah. Now, would you even go to the wedding? No, right? I wouldn't. I wouldn't. Yeah. That friendship is over. She's gone. She's gone. She's going to move to Alabama and she's not going to be allowed to talk to her friends after a certain amount of time. That's actually probably true. So what's the point? Men that are that controlling often are like, well, no, you can't talk to these friends. I had one friend who, like, her controlling husband cut her off from, like, her two gay best friends because they introduced her to her ex-boyfriend. Like, it's just when it gets to this point of so controlling, it's like, it doesn't make any sense.

So I would not be surprised if they got cut off. So let her know you're here for her and I think, yeah, you have to bow out. And in a very loving way, just say I can't support this. You have to find an analogy or a comparison that will strike a chord. And hopefully your lack of participation in her wedding will be a wake-up call. Yeah. And you know what? Sometimes weddings get canceled.

So. Yeah. You should listen to your friends when they know better. Yes, you should. And when a group of people is telling you something, like you could, obviously, you can't that everyone knows better than you, but when a group of people that care about you tells you something, you need to fucking listen. Those are your friends. For me, when I was in a similar sort of situation as this friend, it was like, oh, all my college friends and all my high school

friends and my family, like these different groups who I knew all loved me and were all telling me the same thing about this person. I was like, oh, I still think this is great, but like maybe I should leave because all these people are upset for me. You know, and that was what was the catalyst, and two weeks later I, like, snapped out of it. And I was like, oh, wait, it's terrible. Yeah. All right, Carly, wish you the best of luck, and you have some hard conversations ahead of you. And they told her how they felt? Oh, yeah. Yeah. Okay. All right. Well, we'll take a quick break and be back with a question. Okay. A decade ago, I was on the trail of one of the country's most elusive serial killers,

but it wasn't until 2023 when he was finally caught. The answers were there. hidden in plain sight. So why did it take so long to catch him? I'm Josh Zeman, and this is Monster, hunting the Long Island serial killer, the investigation into the most notorious killer in New York, since the son of Sam, available now. Listen for free on the IHeart Radio app, Apple Podcasts,

wherever you get your podcasts. Hey there, Dr. Jesse Mills here. I'm the director of the men's clinic at UCLA Health, and I want to tell you about my new podcast called The Mailroom. And I'm Jordan, the show's producer. And like a lot of guys, I haven't been to the doctor in many years. I'll be asking the questions we probably should be asking, but aren't. Because guys usually don't go to the doctor unless a piece of their face is hanging off or they've broken a bone.

Depends which bone. Well, that's true. Every week, we're breaking down the unique world of men's health, from testosterone and fitness to diets and fertility and things that happen in the bedroom. You mean sleep? Yeah, something like that, Jordan. We'll talk science without the jargon and get you really. answers to the stuff you actually wonder about. It's going to be fun, whether you're 27, 97, or somewhere in between.

Men's Health is about more than six packs and supplements. It's about energy, confidence, and connection. We don't just want you to live longer. We want you to live better. So check out the mailroom on the IHeart Radio app, Apple Podcasts, or wherever you get your favorite shows. What do you get when you mix 1950s Hollywood, a Cuban musician with a dream, and one of the most iconic sitcoms of all time. You get Desi Arnaz, a trailblazer, a businessman, a husband,

and maybe, most importantly, the first Latino to break prime time wide open. I'm Wilmer Valderama, and yes, I grew up watching him, probably just like you and millions of others. But for me, I saw myself in his story. From planning canary cages to this night here in New York, it's a long ways. On the podcast starring Desi Arnaz and Wilmer Valderrama, I'll take you in a journey to Desi's life, The moments it has overlapped with mine, how he redefined American television, and what that meant for all of us watching from the sidelines, waiting for a face like hours on screen.

This is the story of how one man's spotlight lit the path for so many others and how we carry his legacy today. Listen to starring Desi Arnaz and Wilmer Valderrama. That's part of the MyCultura podcast network available on the IHard Radio app, Apple Podcasts, or wherever you get your podcast. What up, y'all? It's your boy, Kevin on stage. I want to tell you about my new podcast called Not My Best Moment, where I talk to artists, athletes, entertainers, creators, friends, people I admire who had massive success about their massive failures.

What did they mess up on? What is their heartbreak? And what did they learn from it? I got judged horribly. The judges were like, you're trash. I don't know how you got on the show. Boo, somebody had tomatoes. I'm kidding.

But if they had tomatoes, they would have thrown the tomatoes. us. Let's be honest, we've all had those moments we'd rather forget. We bumped our head. We made a mistake. The deal fell through. We're embarrassed. We failed. But this podcast is about that and how we made it through. So when they sat me down, they were kind of like, we got into the small talk and they were just like, so what do you got? What? What ideas? And I was like, oh, no. What? Check out not my best moment with me, Kevin on stage on the Iheart radio app, Apple podcast, YouTube, or wherever you get your podcast. Hi, I'm Dr. Priyank Wally. And I'm Hurricane DeBolu. On our new podcast Health Stuff, we demystify your burning health questions. You'll hear us being completely honest about our own health. I'm talking about very serious stuff right now, and you're laughing at me. And you'll hear candid advice and personal stories from experts who want to make health care more human.

Sometimes you're there to listen, to understand, to empathize, maybe to give them an understanding or a name for what's going on. That helps people a lot, understanding that it's not just in their head. We are breaking down the science, talking with experts, and sharing practical health tips you can actually use in your day-to-day life. From when to utilize and avoid artificial light to how to sleep better. Everything you need to know about fiber and how to poop better. How to minimize the effects of jet lag and how to stay hopeful in times of distress. We human beings, all we want is connection. We just want to connect with each other.

We want to make health less confusing and maybe even a little fun. Find health stuff on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. And we're back. All right. So Jeff says the subject of his email is, am I a ho or just a guy? Dear Chelsea, my boyfriend and I have been going out for eight months and he's a good guy. The problem I'm having now is partway through. I realized I'm not meant for a monogamous relationship all my life.

When we met, that's what I thought I wanted, but learned further on. that this might not be the case. I told him this one day and he acknowledged it and thank me for sharing, but it never came up again, and I've not yet asked to open things up. My issue is I'm in a great relationship, but our sex life has fallen flat, and frankly, he doesn't offer the dominant energy I like sometimes. I spend a lot of my workday being in control of things, so sometimes it's fun to let someone else take over, but he doesn't seem to naturally have that side to him, a.k.a. he has low top energy. I have told him, I'd like him to top sometimes, but it seems like he would need to force that side of him. To make matters more complicated, I have developed

quite the crush. It's nothing crazy or consuming or really anything yet. He's a bartender at a spot where I like to get a drink after work, but what I have to note is my inability to speak to him. Just the thought of talking to him puts my stomach in my throat. I don't usually get that way, but he quite possibly could be the most attractive guy I've ever met. I'll get mesmerized watching a bartend. Another bonus, as I think other hospitality professionals are wired the same way I am. I want to see what other connection I could have with him beyond liking what I see, but obviously there's some guilt being in a relationship, so I keep my distance. I'm going to finish this where I started. Am I a ho, or do you think this is normal for guys wanting a relationship but

also to have sex with other people? Am I awful for having a crush when I'm already in a committed relationship? Am I awful for wanting to possibly be open one day? Jeff. Hi, how are you? Oh, I'm so good. This is like the best day of my life right now. You have no idea. I love it. I love it. First all, you're a gay man, so everything you're feeling is completely natural. Did you have a conversation about opening up your relationship, or you were just thinking about having a conversation? So can I just also first say that I don't say the word ho in a malevolent. No, me. Me neither. I'm a ho too. Okay. Thank you. Because that's not, I get it. That's not how I mean it. No, no, no. You don't have to explain yourself. We're a whole positive. You're in a safe place right

now. Safe, a ho positive place. I appreciate that. So I did one day, you know, and that, you You know, it's funny. I think it's from actually hearing some of your podcasts on my drive where I kind of rethought about this, where I was like, I don't know if monogamy forever is fair. I just think it's a lot to ask now. It is. And I kind of brought it up where I said, you know, I know when we met, I said, I thought I wanted something very, I would say normally monogamous or whatever. But I've kind of changed my mind on that. And I may want to change things at some point. And he kind of was just like, okay. And it never came up again.

Okay. So you have two options. You can either pursue this behind his back and cheat on him or you can go to him and be like, let's revisit the conversation about having an open relationship. Yeah, but I don't, I never want to become the cheater. I've never cheated on anybody in my life. I don't want to start today. Great.

So then that's your answer. But, you know, it's one of those things where it's like, well, if one, day, you know, let's take the crush totally out of the equation for a second. If one day I want to be open, I kind of was saying to Catherine in my pre-interview, like, how do I ask for that without making him feel unloved or small or anything negative? Well, I think you just have a really honest conversation like what you said in your letter. Like, listen, we're in a relationship. Obviously, you're hoping for it to be long term. It is long term already. How long have you guys been together? Probably nine going on in 10 months. So, oh, 10 months.

Months. Okay, okay, copy that. Okay, so what you're, but you're hoping to be at a long-term relationship. I'm enjoying what it is right now. I don't feel the need to change it. It's just, you know, I've always kind of been one of those people who's like, I don't know what life's going to throw at me one day. So it's hard to say, well, I, you know, definitely pan out with this person forever. So I guess maybe that's why the openness is kind of on my mind. But don't you want to pursue this other guy at work that you're talking about? I do, but I just think I'm going to get myself. into trouble if I do it. So, like, because I just think there's going to be no, like, honest way to do it without

it being, like, kind of deceptive or feeling, like, you know, kind of criminal. So I kind of just don't want to do it. I think the way to do that is to have the conversation. And it sounds like he wasn't, he didn't shut it down right away. I mean, an okay is like a, all right, like, let's revisit this later. Yeah. I mean, the way to not feel criminal or deceptive is to have the conversation with him now and be like, okay, I know we talked about this before.

but do you want to like formally have an open relationship? I think that will be healthy moving forward. Like eight or nine months, if you already guys aren't having like hot sex at eight or nine months together, the likelihood is that you're not going to stay together for that much longer. You know what I mean? That's just like kind of gay male behavior. You guys want action.

And it should be your honeymoon period is usually more than eight or nine months. Yeah, I agree. I think it should be at least. That's, you know. But it's a great practice to just have an honest conversation. He seemed to open to it. It might be the easiest thing in the world to say, hey, can we open up our relationship? What are the rules?

Do you want to know, like, are we going to be open and just not tell each other? Or are we going to be open and tell each other? It's probably the healthiest to be open and not divulge every single detail. But what do you feel comfortable with knowing? And, you know, without making it about a specific person like the guy that you're referencing, just say, as a general rule, I've been thinking about it and I would like to keep my options open, although I would like to remain in this relationship. you know, and be really respectful of you.

I want to make sure you're comfortable with this and just come to an agreement where you're both having input. Okay. Yeah, I think I could do that. It's a totally acceptable thing to do, especially as a gay man. It is totally fine for you to do that. It's not going to be that disruptive, especially since you already introduced the topic. Yeah, I suppose so.

I just, I do worry about hurting his feelings, I guess. Doesn't seem warm to it. It's more hurtful to be dishonest and deceptive. So it's more, you know what I mean? that's, you don't carry his feelings for him. Give him enough credit, have enough respect for him that you actually give him the truth of the matter and how you're feeling. And then let him tell you how that makes him feel. Yeah. And it can be an ongoing conversation. Like he doesn't have to like say yes after the first conversation that you both go out and sleep with other people.

Like that's, it's just opening up the conversation about opening things up. The other thing I wanted to address is you say, you know, you said like, oh, I'm not sure if I can like force him to do this. Like, being in a relationship with someone is all about experimenting, especially in the bedroom. And I think, like, there's definitely room for, you know, things to change, things to evolve. I mean, Brad and I have been together 20 years. And I would say even in the last, like, three or four years, things are still evolving. Yeah, now he calls her Chelsea. Which is really weird in bed, but, you know. And unprofessional. Workplace. But yeah, I mean, I think I would just, like, tell him like, hey, I'm thinking about this. I would love if you do this in bed, if you're a little more

controlling, et cetera, et cetera. And like, see if he is into it. Yeah, I mean, listen, you're at a great place in your relationship to start having really honest conversations because that is also a sign of how long the relationship can last. If you can tell somebody something that is, you know, hard for you to say or opens the doorway to like a further conversation about sexual freedom, about sexual liberty, about how you're going to move around in this relationship, you're only going to, like, build a stronger foundation. Stronger foundation for moving forward and with other relationships if this relationship doesn't last long. But I think you should also give him more credit than you're giving him. Like, don't be so worried about his feelings until there's something to worry about.

But being honest and forthright and upfront with your partner is the most respectful way you can behave. Okay. Yeah. I think you're right. Maybe I'm kind of like anticipating the worst maybe, which is something I've professionally doing. Stop that. Sure. Right. Right. Okay. Okay. Good, good. All right. Thanks, Jeff. And then hopefully you can go fuck that guy that you want to fuck. Yeah.

Please report back when you fuck that guy. All right. Yeah, no, I'll definitely follow up with you. I mean, maybe your boyfriend wants to go fuck that guy with you. Who knows? Yeah, yeah. That's actually a great idea. Yeah.

Love it. Yeah, I mean, anything's possible. Sure. All right. Thanks, Jeff. Bye, Jeff. Thanks so much. Nice to me.

Take care. Okay. Yeah. All right. Well, we're good to go and round. Okay. And we're wrapped on another episode of Deer Chelsea. Thanks, guys, for listening.

Make sure you go to Chelseahandler.com to find tickets for my stand-up shows. Come see me. Come see me live. It's going to be a good time, guys. I just announced all my tour dates. It's called the High and Mighty Tour. I will be touring from February through June. So go get your tickets now.

If you want to come see me perform, I will be on the High and Mighty Tour. Do you want advice from Chelsea? Write into Dear Chelsea Podcast at gmail.com. Find full video episodes of Dear Chelsea on YouTube by searching at Dear Chelsea Pod. Dear Chelsea is edited and engineered by Brad Dickert, executive producer, Catherine Law. And be sure to check out our merch at chelseahandler.com. I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money.

And now we're back making this new podcast called Business History about the best ideas and people and businesses in history. And some of the worst people. ideas and destructive companies in the history of business. First episode, how Southwest Airlines use cheap seats and free whiskey to fight its way into the airline is. The most Texas story ever. Listen to business history on the IHeart Radio app, Apple podcasts, or wherever you get your podcasts. Hey there, Dr. Jesse Mills here. I'm the director of the men's clinic at UCLA, and I want to tell you about my new podcast called The Mailroom. And I'm Jordan, the show's producer. And like

most guys, I haven't been to the doctor in way too long. I'll be asking the questions we probably should be asking, but aren't. Every week, we're breaking down the world of men's health from testosterone and fitness to diets and fertility. We'll talk science without the jargon and get your real answers to the stuff you actually wonder about. So check out the mailroom on the IHeart Radio app, Apple Podcasts, or wherever you get your favorite shows.

Podcasters, it's time to get the recognition you deserve. The IHeart Podcast Awards are coming back in 2026. Got a mic? Then you've got a shot. Every year, we celebrate the most creative, compelling, and game-changing voices in podcasting. Is that you? Submit now at iHeartPodcastawards.com for a chance to be honored on the biggest stage in the industry. Deadline December 7th.

This is your chance. Let's celebrate the power of podcasting and your place in it. Enter now at iHeartPodcastawards.com. What up, y'all? It's your boy, Kevin on stage. I want to tell you about my new podcast called Not My Best Moment, where I talk to artists, athletes, entertainers, creators, friends, people I admire who had massive success about their massive failures. What did they mess up on? What is their heartbreak? And what did they learn from me?

I got judged horribly. The judges were like, you're trash. I don't know how you got on the show. Check out Not My Best Moment with me kept on stage on the IHeart Radio app, Apple Podcasts, YouTube, or wherever you get your podcast. On this week's episode of next chapter, I, TD Jake, sit down, with Denzel Washington, a two-time Academy Award-winning actor and cultural icon, for a conversation about change, identity, and the moment everything shifted. I mean, I don't take any credit for it. It's nothing I did as special, you know, didn't knock down a few pegs and recognize it, but I just didn't put me first. I just put God first, and he's carried me.

Whether you're rebuilding, reimagining, or just trying to hold it together, this one will speak to you. Listen to the next chapter podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. New episodes drop weekly. Don't miss one of them. This is an IHeart podcast. Guaranteed human.

Thank you.