Life Will Be the Death of Me with Chelsea Handler - Minisode: Verging on Lesbian with Chelsea + Catherine

Episode Date: November 14, 2025

Chelsea and Catherine get a followup from a baby mama who fell out of love… and follows her heart into a whirlwind engagement with a small-town boy. And a couple chooses to live apart after their kids don’t mesh. * 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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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. 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. Hi, Catherine. How's it going?

Hi, Chelsea. It's going pretty good. It's going pretty good. I have a follow-up. Okay. And it is a wild one. So this is Victoria who called in on our Karamo Brown episode. She was in the situation where she like had a couple kids, I think, with her baby daddy and loved him in a platonic way, but wasn't in love with him anymore. And she was like, I'm basically bisexual, verging on lesbian and want to experiment over there and kind of had started doing that. I like verging on lesbian.

Verging. Aren't we all verging on lesbian? I think so. So, yeah, she was sort of ready to blow up her life and leave. and the advice was like, it's time. Like if you keep cheating with women, like it's time. So I asked her what's been up. She said, oh my God, girl, it's been a roller coaster.

It's a very long story, so good luck editing it, ha ha. Did I take Chelsea and Karamo's advice? Yes and no. I listened to every episode and I'd say it was one of the more harsh reactions to a listener's problem than most. Even my girlfriends that I shared the episode with were like, damn, they gave it to you.

I continued to try and date girls and even got a little serious with one. We went on several dates, including going to her place where she cooked me pasta, and it ended in a lovely makeout session. But even though my baby daddy was aware of the entire thing and knew I had a dating app specifically for hooking up with girls, he still made a huge fuss about it and was truly hurt by it. Shit has now seriously hit the fan because I headed to beautiful Northern California for my dear 103-year-old grandma's funeral a few months ago and ended up meeting a guy, Gasp, while out there. It was truly love at first sight.

He wasn't looking for love, and I sure as hell wasn't looking for love with a man, but he fit my male physical type completely. I take it as my sainted grandmother's party gift to me. She lived in a teeny tiny town, and never ever have I ever run into such a beautiful man in the many, many times I have visited over the years. Because I was with family, we didn't really get to hang out while I was in town, but I got his number, and literally the next day, we made plans to meet up in LA. He would fly down from NorCal, and I would fly from the East Coast. Fast forward a month, baby daddy finds out about him and I had to cancel my trip. This new guy is such a peach that he changed his flight and plans around and flew out to me instead. We had the most amazing

weekend together and officially started our relationship. It gets crazier. We decided he would come out to me again for my birthday, which would be a couple of months later. But in the meantime, I decided that would be too long. So I planned a surprise trip out to see him along with a surprise engagement. We were at a restaurant and I hopped on the band's mic, professed my love to him in front of the entire small town of 7,000 people, gave him a ring, and he eagerly said yes. I hired a photographer and we took the most amazing pictures. Unfortunately, I have two kids and he has two kids, so neither of us have the ability to move across the country for the other with our respective baby parents. But we're so in love and so committed. He knows I'm bi and

although he's not enthusiastic about sharing me, he knows that possibly bringing a girl into the bedroom would bring me joy and he's okay with that. His only boundary is me hooking up with other guys, which I have zero intention of doing. So yes, I still want to explore things with girls, but now I've found true love. And if it happens with women, I know my partner will be okay with it. I drunkenly made out with a female coworker recently and he brushed it off as nothing. So I can confirm this is the case. As far as baby daddy goes, we still live together because we own our house together and it needs works. We can't just sell it tomorrow. We live in a high cost area and neither of us could buy the other out or afford mortgage and a rent. So I'm stuck in this terrible

living situation until we fix up the house and sell it, which I'm in the process of doing. while also applying to school, working full-time, maintaining some sort of social life, juggling a long-distance fiancé, and taking care of two kids. Let me know if you have any follow-up questions. XO Victoria. And there's a picture of her with the very hot guy. Well, it just turns out you weren't into your boyfriend, period.

Like, I fucking told you. Didn't I tell her? Yeah, that was the thing. We're like, we've got to dump this guy. Okay, so it takes another man for you to realize that you have to get out of your situation. I guess so. I guess so. I love how men are like, it's okay if you hook up with women,

but not another man. That's how little they think of women. That's very homophobic. You can cheat with a girl but you can't cheat with a guy. Why?

What's the fucking difference? I know. It's a little homophobic too because it's like, well, that's not real cheating. Yes, exactly. It totally is. It's all kinds of,

there's all sorts of wrong things with that. Well, Victoria, I wish you the best. I do too, Victoria. And it sounds like you do need a harsh critic. So I'm here for you

whenever you need one. All right. Follow up with us when and if anything changes. 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. 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 gonna have to look up this story i'm obsessed i'm obsessed from best-selling 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.

Hey, this is Hayes Davenport. And Sean Clements. We host the podcast Hollywood Handbook on the Big Money Players Network. Our show is extremely accessible to first-time listeners. Each week, we talk to someone in show business, a.k.a. 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 shape this? How about we flip it on its head? 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 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 They're so stupid. Everyone's so dumb except for you. And fake. Right, fake 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 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. 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. This is kind of an interesting one. I'm interested in your perspective on this. Michelle says, Dear Chelsea, My boyfriend and I have been together for about eight years

and have lived together for the last two and a half. Recently, issues with our blended family have come to a head and we've decided to live separately. Even though I'm the one that initiated this, I'm having a hard time with it. It seems like a step back, not forward. He has a 22-year-old son who lives with us and a 24-year-old daughter who doesn't,

and I have a 13-year-old daughter. I can't say one specific thing that has happened to come to this decision. It's more like death by a thousand cuts. I have come to terms with us living apart, and what I'm having a hard time with is how to move forward and make things work with me and my boyfriend. He thinks my daughter is rude and has made it clear that he doesn't think he'll ever be able to have a relationship with her. I'm not going to say that she's perfect and never talks back, but as far as 13-year-old girls go, I think she's better than most. He brings a lot of value to my life, and we have a lot of fun together. I'm feeling a bit stuck. Do I just see how things go? Maybe when she's out of the teen years, it will get better.

I appreciate any help. Michelle. Hi, Michelle. Hi, how's it going? Good. How are you doing? Good. I have a friend who just went through this exact same situation. They had a blended family. She has a son and her partner had a daughter and a son, has a daughter and a son. They were trying to move in together. They tried to blend their families together and it was a no-go. There was no gelling happening between the kids. So they ended up buying a house, like a house for them to be in, in the middle and like to share. And then they each, and then they had another house and basically it just all kind of fell apart. They didn't break up. They stayed together and just let it go. They're like, it's not going to work. We're not going to live together. We're

not blending our families. It's just not working. Now they're engaged to get married. So I, they just gave it a year or two, everything calmed down. The kids got a little bit older, everything started to gel. And by being apart, it actually magnified the reason that they were together in the first place. They didn't break up. They stayed together, just like you and your boyfriend are going to stay together. So what I would say to you is don't be attached to the idea of the fact that you're like separating and living in different houses, that that's going to have, that you're breaking up. You're not. You're doing what's right for your families and for your kids. And you can still have, in some senses, an even stronger romantic relationship

because you don't live together. Yeah. I mean, that's what I'm hoping for. I, you know, I feel like what we're doing now just doesn't work. Right. So it's either gonna, you know, make it or break it. Right. Maybe it's just time will tell. But, you know, we have been together for eight years. And if he hasn't been able to form a relationship with my daughter yet, like I'm just, if it's been eight years and he hasn't formed a relationship with her, like is he going to be able to? And then. My friend had the same problem with it. This is the same exact thing. She wanted this man to be the father that her son never had. And it's just not going be what she had imagined. There is a relationship there, but I understand what you're saying,

but I think you have to not put so much pressure on their relationship, especially if you guys aren't living together. You can't force a relationship like that. And yeah, while it's not your ideal, is it worth breaking up over it? Does she dislike him, your daughter? No, I don't think it's that she dislikes him. I think it's almost like she's just kind of indifferent, I guess. Uh-huh. Well, maybe if the pressure is taken off of the situation, that allows them to have a much more natural, organic.

She's only getting older and more mature. So the chances of them connecting and having a more calm, respectful relationship are bound to increase with age and her maturity, right? And with the pressure taken off of the situation, I really believe that will yield better results. Yeah. Grown men, like, don't know what to do with a 13, like, how to communicate with a 13-year-old girl. They don't know what to do with many things.

So I wouldn't worry about that. And don't put so much pressure on their relationship. Like, take a step back from that and focus on your relationship with your daughter. Yeah. And I think, you know, when we do move out, you know, looking forward to it just being us and all the things that come along with that yeah she's at the age where she like shares my clothes and like can you know she'll be able to just kind of come and go out of my room like it'll just be a little different yeah and you're and you're never gonna get that time back with your

daughter so enjoy that this guy's gonna be around he's been around for eight years you can have you know what I mean focus on your time with your daughter and make sure that she knows you're there for her that's even more important overall is that you're leaving you know moving out for the benefit you know of her really so that you can be with her like their relationship isn't is that how it's being presented to her like what how is it being presented to your daughter I presented it to her like it's just not working for anybody which is the truth yeah it's not working for you know him his son me my it's not working for anybody so that's kind of how I presented it and that's a great that's great parenting yeah you're putting aside your needs

and wants for what's best for you and your child and that's what you should be doing yeah so that's good this is a good thing this isn't a negative thing you're not breaking up it's all positive it's all in a sign of maturity like don't hold on to the idea that they have to have this relationship that you envision that is not what's going to happen they're going to have a relationship it will most likely improve over time. I know it's already been eight years, but she's how old is she now? 13. Okay, so there you go. So that's perfect. So take this time with her treasure it. Enjoy yourself. Enjoy the distance of not having to sleep in the same bed with your fucking boyfriend every night also. Right? Yeah. And your daughter's gonna be stoked to have you all to

herself. Yeah, well, yeah, I think it's all good things. Yeah. Yeah. I mean, you know, I feel good about the decision. I was, you know, leading up to, I was like going back and forth. But then when I finally made the decision, like, you know, I like, I like, this is what I don't have any doubts that I don't want to move out. This is definitely what I want to do. Right. Good. Yeah. All right, Michelle, thank you for calling in. All right. Thanks guys. Bye. Bye Michelle. Take care. Well, that was an interesting one. Yeah, I like a modern family. Yeah, I do too.

Okay, and we're wrapped on another episode of To Your Chelsea. Thanks, guys, for listening. Come see me. Come see me live. It's going to be a good time, guys. Bye. I just announced all my tour dates. They just went on sale.

It's called the High and Mighty Tour. I will be starting in February of next year. So 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 DearChelseaPodcast 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 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 listen to pro society on the iheart radio 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 kristin bell josh gad and adina 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

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 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.