Life Will Be the Death of Me with Chelsea Handler - 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.

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And will you finish episode eight before you're done slicing the cucumbers? Get Bell Pure Fiber Internet with Crave, Netflix, and Disney Plus from $94 a month. Price guaranteed for two years on internet with a two-year term and auto pay credit. Visit bell.ca for details and to check availability.

Bell. Connection is everything. I survived nine months in captivity, and I've spent my life exploring how other people survive what should have destroyed them. I'm Elizabeth Smart, and these are The Survivor Files. Every week, I'm with survivors who lived through the unthinkable, abducted, stalked, controlled, and nearly silenced. These are stories about what it takes to make it out alive. Listen to The Survivor Files with Elizabeth Smart on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

If your bookshelf and your For You page are equally important to your personality, welcome home. Pro Society is a weekly podcast that's part book club, part group chat for anyone who thinks Pride and Prejudice and Love Island deserve the same level of discourse. Each week, we're connecting the dots between books, the internet, and pop culture with your favorite writers, book talk creators, and plenty of overthought opinions. Yeah, I'm obsessed. I'm obsessed. Listen to Pro Society on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Did you hear the new episode of the Hey Jonas podcast? We are at D23, so we'll see who stops by.

The cast of Frozen stopped by. Kristen Bell, Josh Gad, and Idina Menzel. I auditioned for Frozen. What? For Kristoff. They said, okay, what are you going to be singing today? I said, I don't know. That must have been why you didn't get it.

Oh, you probably won. Plus, John Stamos, Hayden Christensen from Star Wars, and more. And I guess I can share that, uh, no way. Listen to the latest episode of Hey Jonas on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. On the new podcast, Solita, we share the messy reality of traveling alone as a woman. I can wait four hours for the next bus,

or this random dude is offering me a ride on his motorcycle. I chose option B. I'm Julie Pinheiro, and I travel by myself because it's a rare space where I can say yes without asking anyone else first. I'm on a mission to reclaim the word solita, trading the pity for possibility. Listen to Solita on the iHeartRadio app,

Apple Podcasts, or wherever you get your podcasts. Hi, Catherine. Hi, Chelsea. Hi. What are we doing? We're doing a mini-sode today. Today's welcome to our mini-sode. 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 prenup. 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. 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 to how I'm going to stand up for myself.

It's always about 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, like if 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. 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. In a 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 obviously you can't assume 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, that'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? Mm-hmm. Oh, yeah. Yeah. Okay.

All right. Well, we'll take a quick break and be back with a question. Okay. Behind every night spent making the kids' lunches, there's a lot of suspense. Will they finally eat the veggies? Will the pesto survive the first bite? Will the lunchbox come home empty, half full, or come home at all? And will you finish episode eight before you're done slicing the cucumbers?

Get Bell Pure Fiber Internet with Crave, Netflix, and Disney Plus from $94 a month. Price guaranteed for two years on internet with a two-year term and auto pay credit. Visit bell.ca for details and to check availability. Bell. Connection is everything. When I was 14 years old, I was kidnapped and held captive for nine months. I survived, and I've spent my life exploring how other people survive what should have destroyed them. I'm Elizabeth Smart, and these are the Survivor Files. I just remember this low, taunting voice next to my ear saying, shut up, don't say anything.

Every week, I'm with survivors who live through the unthinkable. I knew if he woke up, without a doubt, he was going to hurt me. I started feeling that there was someone at the end of my bed, and I just started screaming. They are abducted, stalked, controlled, and nearly silenced. but these aren't stories about what's taken from them. They're stories about what it takes to make it out alive. Listen to The Survivor Files with Elizabeth Smart on the iHeartRadio app, Apple Podcasts,

or wherever you get your podcasts. If your bookshelf and your For You page are equally important to your personality, welcome home. This is Prose Society, the weekly podcast that's part book club, part group chat for thought daughters, pop culture obsessives,

and anyone who thinks Pride and Prejudice and Love Island deserve the same level of discourse. I'm Eli Rallo, and every week we're connecting the dots between books, the internet, and the conversations everyone can't stop having. I'm going to have to look up this story. I'm obsessed. I'm obsessed. From bestselling authors and your favorite book talk creators to the latest pop culture moments, nothing is off the table. It's like if you can hide some real messages inside compelling characters, then that is a Trojan horse.

Whether you're looking for literary deep dives, smart pop culture conversations, or a community of readers who love to think a little too much, you're in the right place. Listen to Pro Society on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. See you between the pages. On the new podcast, Solita, we share the messy reality of traveling alone as a woman. I can wait four hours for the next bus or this random dude is offering me a ride on his motorcycle. I chose option B. I'm Julie Pinheiro, and I travel by myself because it's a rare space where I can say yes without asking anyone else first. I'm on a mission to reclaim the word solita, trading the pity for possibility.

Every time I tried to be alone, I kept meeting people, and they were like, you smiled at us. Not a lot of people smile around here. It's when you're alone that you're most receptive to the world as it is and not the lies you're sold about it. It can be a time where you push your limits, change your mind, or wake up to a new version of yourself. So whether you're a solo travel veteran or you're too nervous to book your first trip, I hope you listen to Solita on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. in show business aka the biz and try to help them with their careers and see what they have to offer us everyone has a good time and no one gets mad at their publicist for letting them do

our show we've had a lot of great guests like sarah sherman not that great actually can you help me can can you help me shape this yeah how about we flip it on his head right how about we flip this around okay what is the surprise woman who actually you think is the straight man is actually the one who's acting weird adam scott this entire time you've been expecting adam sandler to come to visit the show i i would never let go of that i have i would never set expectations for something like that it seems like if the universe allows for something like that to happen i'm open to it i'm always going to accept you know danny mcbride fine yeah it's all this fragile masculinity exuding i could smell it walking down the hallway to be honest with you

i was like is that weed nope it's fragile masculinity ben stiller no because a lot of times in out of context people don't get it or even know what a circle is you know what i mean like you're like oh what's this state everyone's so dumb except for you fake right fake and and also not interested or just like oh i've got my life i don't care about your life and a lot of other big shots that wouldn't be where they are without us oh and by the way will ferrell told us personally he loves the show and he wants to be a guest on every episode but he's just so busy listen to hollywood handbook on the iheart radio 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 hoe 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 thanked 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,

aka 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 hoe, 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 of 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 hoe in a malevolent

Me neither. I'm a ho too. I want to fuck people all the time. That's not how I mean it. No, no, no, no. You don't have to explain yourself. You're in a safe place right now. Safe, ho, positive place. I appreciate that. So I did one day, you know, and 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 could 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. 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, 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, 10 months. Oh, 10 months. Okay. Okay. Copy that. Okay. But you're hoping to be in 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, cause 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're already guys aren't having like hot sex at eight or nine or eight, 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 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 healthiest to be

open and not divulge every single detail but what do you feel comfortable with knowing and 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. It doesn't seem warm to it. It's more hurtful to be dishonest and deceptive. So it's more, you know what I mean? 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. He doesn't have to say yes after the first conversation. You both go out and sleep with other people. It's just opening up the conversation about opening things up. The other thing I wanted to address is you said, oh, I'm not sure if I can force him to do this. Being in a relationship with someone is all about experimenting, especially in the bedroom.

And I think there's definitely room for things to change, things to evolve. I mean, Brad and I have been together 20 years. And I would say even in the last three or four years, things are still evolving. Yeah, now he calls her Chelsea. Which is really weird in bed. 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'm professionally doing. Yeah. So stop that. Stop that. Sure. Right. Right. 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. Alrighty. 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 meet you. Take care.

Okay. Yeah. All right. Well, we're good to go on round. Okay. And we're wrapped on another episode of To Your 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. Bye. 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 katherine law and be sure to check out our Merch at chelseahandler.com. I survived nine months in captivity, and I've spent my life exploring how other people survive what should have destroyed them. I'm Elizabeth Smart, and these are The Survivor Files. Every week, I'm with survivors who live through the unthinkable,

abducted, stalked, controlled, and nearly silenced. These are stories about what it takes to make it out alive. Listen to The Survivor Files with Elizabeth Smart on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. If your bookshelf and your For You page are equally important to your personality, welcome home. Pro Society is a weekly podcast that's part book club, part group chat for anyone who thinks Pride and Prejudice and Love Island deserve the same level of discourse. Each week, we're connecting the dots between books, the internet, and pop culture with your favorite writers, book talk creators,

and plenty of overthought opinions. Yeah, I'm obsessed. I'm obsessed. Listen to Pro Society on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Did you hear the new episode of the Hey Jonas podcast? We are at D23, so we'll see who stops by. The cast of Frozen stopped by. Kristen Bell, Josh Gad, and Idina Menzel.

I auditioned for Frozen. What? For Kristoff. They said, okay, what are you going to be singing today? I said, I don't know. That must have been why you didn't get in. Plus, John Stamos, Hayden Christensen from Star Wars, and more. And I guess I can share that, uh...

No way. Listen to the latest episode of Hey Jonas on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. On the new podcast, Solita, we share the messy reality of traveling alone as a woman. I can wait four hours for the next bus, or this random dude is offering me a ride on his motorcycle. I chose option B. I'm Julie Pinheiro, and I travel by myself because it's a rare space where I can say yes without asking anyone else first. I'm on a mission to reclaim the word solita, trading the pity for possibility. Listen to Solita on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Hey, this is Hayes Davenport. And Sean Clements. We host the podcast, Hollywood Handbook. Each week, we talk to someone in show business and try to help them with their careers and see what they have to offer us. Everyone has a good time, and no one gets mad at their publicist for letting them do our show. We've had a lot of great guests like Sarah Sherman, Adam Scott, Danny McBride, Ben Stiller, and a lot of other big shots that wouldn't be where they are without us. Listen to Hollywood Handbook on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

This is an iHeart Podcast. Guaranteed human.