Minisode: Verging on Lesbian with Chelsea + Catherine

Summary

Dear Chelsea – Minisode: Verging on Lesbian with Chelsea + Catherine

Podcast: Dear Chelsea (iHeartPodcasts)
Hosts: Chelsea Handler and Catherine Law
Date: November 14, 2025

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Episode Overview

In this lively minisode, Chelsea Handler and co-host Catherine Law catch up with a previous listener, Victoria, whose story first stirred the pot in an earlier episode with Karamo Brown. Victoria, formerly entrenched in a “platonic but not romantic” relationship with her children’s father and in the midst of exploring her bisexuality, offers a wild update—one involving female dating, an unexpected new male love, and a dramatic engagement. The hosts dissect her journey with humor and candor before advising another listener struggling with the challenges of blended families and cohabitation.

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Key Discussion Points and Insights

Listener Update: Victoria’s Rollercoaster Romance

(Segment begins ~04:01)

• Background:
  Victoria previously wrote in about being in a long-term relationship with her children's father, lacking romantic feelings and feeling "bisexual verging on lesbian." She was contemplating leaving him after multiple affairs with women.

• Victoria’s Update:

  • She took Chelsea and Karamo’s prior advice (“dump those guys”), but in a non-linear way.
  • Continued dating women, including a budding relationship with one who cooked her dinner and ended the night with “a lovely makeout session.”
  • Her ex-partner ("baby daddy") was kept in the loop but hurt by her dating activities.
  • During her grandmother’s funeral, she unexpectedly fell for a man (“love at first sight”). They started a long-distance relationship, and Victoria surprised him with an engagement in his small hometown, complete with a public proposal and photographer.
  • Both have children and geographical constraints that make moving impractical, but remain committed. New fiancé knows she’s bi and is comfortable with her having girlfriends, though not with her dating other men.
  • Victoria continues to co-own a house with her ex and is juggling school, work, a social life, a long-distance fiancé, and motherhood.
  • Concludes with a photo of the "very hot guy."

• Hosts’ Reaction:

  • Chelsea and Catherine recall giving “harsh” but honest advice, focusing on the necessity of leaving a stagnant relationship.

  • Chelsea observes:

    “Well, it just turns out you weren’t into your boyfriend, period. Like I told you. Didn’t I tell her?” (07:47)

  • They critique the double standard in male partners being ok with women dating women, but not other men:

    “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. You know, you can cheat with a girl, but you can’t cheat with a guy.” – Chelsea (08:01)
    “It’s a little homophobic too because it’s like, ‘well that’s not real cheating.’” – Catherine (08:11)

  • Chelsea and Catherine wish Victoria luck and encourage more updates:

    “I do too, Victoria. And it sounds like you do need a harsh critic, so I’m here for you whenever you need one.” (08:23)

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Advice Segment: Blended Family Struggles

(Segment begins ~12:55, caller live at 13:56)

• Caller Michelle’s Situation:

  • Eight-year relationship with boyfriend, living together for 2.5 years.
  • Issues with blending their families: Michelle’s 13-year-old daughter, boyfriend’s 22-year-old son (living with them), and his 24-year-old daughter (independent).
  • Decided to live separately due to persistent tension, especially between boyfriend and Michelle's daughter. Boyfriend doesn’t believe he’ll ever connect with her.
  • Michelle initiated this move but feels conflicted, viewing it as a step backwards but necessary.

• Chelsea’s Advice and Perspective:

  • Chelsea relates a friend’s similar experience with failed attempts at blending families, which eventually led to a healthier relationship once living apart.

    “They didn’t break up, they stayed together and just let it go... By being apart, it actually magnified the reason that they were together in the first place.” (14:01)

  • Chelsea urges Michelle not to pressure herself or the relationship dynamics between partner and child:

    “You can’t force a relationship like that... Is it worth breaking up over it? Like does she dislike him—your daughter?” (15:51)

  • Pressure removal might allow a more “natural, organic” connection as the daughter matures:

    “She’s only getting older and more mature. So the chances of them connecting... are bound to increase with age and her maturity.” (16:36)

  • Emphasizes the value of time alone with her daughter:

    “You’re never gonna get that time back with your daughter. So enjoy that. This guy’s gonna be around... Focus on your time with your daughter and make sure she knows you’re there for her.” (17:37)

  • Validates Michelle’s framing to her daughter, calling it "good parenting," and reassures that the decision is a positive, mature step:

    “That’s great parenting... You’re putting aside your needs and wants for what’s best for you and your child.” (18:14)

• Memorable Moments:

  • Chelsea's frank humor about what grown men know about teenage girls:

    “Grown men like don’t know what to do with a 13... Like how they don’t know what to—do, how to communicate with a 13-year-old girl. They don’t know what to do with many things.” (17:01)

  • Michelle expresses relief upon making the decision:

    “I don’t have any doubts that I don’t want to move out. This is definitely what I want to do.” (19:17)

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Notable Quotes and Memorable Moments

| Timestamp | Speaker | Quote | |------------|-----------|------------------------------------------------------------------| | 07:47 | Chelsea | “Well, it just turns out you weren’t into your boyfriend, period. Like I told you.” | | 08:01 | Chelsea | “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.” | | 08:11 | Catherine | “It’s a little homophobic too because it’s like, ‘well that’s not real cheating.’” | | 14:01 | Chelsea | “By being apart, it actually magnified the reason that they were together in the first place.” | | 15:51 | Chelsea | “You can’t force a relationship like that... Is it worth breaking up over it?” | | 17:01 | Chelsea | “Grown men like don’t know what to do with a 13... Like how they don’t know what to—do, how to communicate with a 13-year-old girl.” | | 18:14 | Chelsea | “That’s great parenting… You’re putting aside your needs and wants for what’s best for you and your child.” | | 19:17 | Michelle | “I don’t have any doubts that I don’t want to move out. This is definitely what I want to do.” |

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Timestamps for Key Segments

• Victoria’s follow-up email: 04:01 – 08:36
• Reflection and discussion on Victoria’s journey: 07:47 – 08:36
• Blended family caller Michelle’s question: 12:55 – 19:28
• Chelsea and Catherine’s perspective and advice: 13:56 – 19:28

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Tone and Takeaways

Chelsea and Catherine’s banter is direct, empathetic, and laced with signature wit. They embrace blunt honesty and encourage self-empowerment, especially regarding relationship authenticity and prioritizing the needs of children in blended family situations. The episode underscores the messiness and unpredictability of personal growth—sometimes what you think you want isn’t the true answer, and sometimes the hard choices lead to surprising, positive outcomes.

Recommendations by Chelsea & Catherine:

• Be honest about what you want, even if it’s a detour from your original plan.
• Don’t force relationships that aren’t working, especially between partners and children.
• Focus on nurturing the relationships that matter most (parent–child bond) during transitional times.
• Remember that unconventional solutions—like living apart as a couple—can sometimes strengthen a relationship.

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This episode is a must-listen for those navigating the complexities of blended families, fluid sexuality, or big relationship transitions—with a healthy dose of Chelsea’s signature real talk.

Transcript

[Chelsea Handler]

This is an I heart podcast.

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Go to 8sleep.com Chelsea use code Chelsea and get up to $700 off Pod 5. You can try it risk free for 30 days. Trust me, better sleep starts here. From nursing and healthcare to business and it Rasmussen has a range of programs to fit your goals and passion for no matter what your day to day looks like. Rasmussen's programs allow you to balance school with life while you pursue your degree. So if you're ready to pursue your education goals, Rasmussen is ready to help you take that next step. Head on over to Rasmussen Edu and check out the opportunities waiting for you. Your future is a bright one. Rasmussen University can help you get there.

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[Chelsea Handler]

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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 on lesbian verging. Aren't we all verging on lesbian? 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're, 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. Haha. Did I take Chelsea and Karamo's advice? Yes and no. I've listened to every episode and I'd say it was one of the more 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 parting 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 work so 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 fiance and taking care of two kids. Let me know if you have any follow up questions. Xo Victoria. And there's Jesus picture of her with the very hot guy.

Well, it just turns out you weren't into your boyfriend, period. Like I told you. Didn't I tell her?

That was the. Yeah, that was the thing. We're like, dump those guys.

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. You know, 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.

Like 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, when and if anything changes.

You know what's not fun?

Waking up at 2am drenched in sweat.

Been there. That's why I started using pod 5 from 8 sleep. And let me tell you, it is a game changer. It's designed with women's help in mind. Especially for those of us dealing with hot flashes. Pod 5 is this genius smart mattress cover that fits over any bed and pulls your body before a hot flash can mess with your sleep. And when I need an extra relief, I just tap the bed or use the app to activate hot flash mode. 30 minutes of instant cooling. It's like having a personal climate concierge. It's clinically proven to reduce hot flashes by over 50% and I genuinely sleep deeper and wake up feeling way more refreshed. I love that it's a non medical solution, but it's backed by real data and it feels totally natural. Anyone who listens to this podcast knows that I would like to sleep in a refrigerator and now I can. And if you sleep with a partner, Pod 5 cools each side of the bed independently. So no more kicking someone out for being a human furnace. You both get your perfect temperature from 55 degrees to 110 degrees.

Go to 8sleep.com Chelsea use code Chelsea and get up to $700 off Pod 5. You can try it risk free for 30 days. Trust me, better sleep starts here. From nursing and healthcare to business and it Rasmussen has a range of programs to fit your goals and passion no matter what your day to day looks like. Rasmussen's programs allow you to balance school with life while you pursue your degree. So if you're ready to pursue your education goals, Rasmussen is ready to help you take that next step. Head on over to Rasmussen Edu and check out the opportunities waiting for you. Your future is a bright one. Rasmussen University can help you get there. The holidays are here, which means I am stressed, over, committed, slightly buzzed and pretending I know how to cook. But at least my dog Doug is thriving. He's eating just fresh from just food for dogs. Real human grade food with none of that processed junk. It's shelf stable, which means I can toss it in my suitcase when I travel or shove it in a cabinet next to my tequila. And honestly, Doug's living his best life. His coat is shiny, he's got energy, and when guests come over, he's the only one not complaining about their food. Meanwhile, I'm over here eating takeout and calling it festive. So this holiday season, give your dog something better than table scraps. Give them just fresh, real food. For dogs who have better taste than we do. Go to justfoodfordogs.com for 50% off your first order. No code, no hassle, and thank God, no cooking required.

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[Chelsea Handler]

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Iheartra 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.

[Michelle (Caller)]

Hi.

[Chelsea Handler]

How's it going?

Good, how you doing?

[Michelle (Caller)]

Good.

[Chelsea Handler]

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 gonna work. We're not gonna live together. We're not blending our families. It's just not working. Now they're engaged to get married. So 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 gonna 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 gonna 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.

[Michelle (Caller)]

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.

[Chelsea Handler]

Right.

[Michelle (Caller)]

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.

[Chelsea Handler]

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 gonna 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. Like you can't force a relationship like that. And yeah. While it's not your ideal, is it worth breaking up over it? Like does she dislike him? Your daughter?

[Michelle (Caller)]

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.

[Chelsea Handler]

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 if 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 they don't know what to.

Do, 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.

[Michelle (Caller)]

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.

[Chelsea Handler]

Yeah.

[Michelle (Caller)]

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.

[Chelsea Handler]

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. Their relationship isn't. Is that how it's being presented to her? Like, what. How is it being presented to your daughter?

[Michelle (Caller)]

I presented it to her. Like, it's just not working for anybody, which is the truth. It's not working for, you know, him, his son, me, my daughter. It's not working for anybody. So that's kind of how I presented it.

[Chelsea Handler]

And that's a great. That's great parenting.

[Michelle (Caller)]

Yeah.

[Chelsea Handler]

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 gonna happen. They're gonna have a relationship. I mean, it will most likely improve over time. I know it's already been eight years, but how old is she now?

[Michelle (Caller)]

Thirteen.

[Chelsea Handler]

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 boyf every night also.

[Michelle (Caller)]

Right. Yeah.

[Chelsea Handler]

And your daughter's gonna be stoked to have you all to herself. Really? Well, this is all. I think, is all good things. Yeah.

[Michelle (Caller)]

Yeah, I. 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.

[Chelsea Handler]

I like.

[Michelle (Caller)]

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. Yeah.

[Chelsea Handler]

All right, Michelle, thank you for calling in.

[Michelle (Caller)]

All right, thanks, guys.

[Chelsea Handler]

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 Dear 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 in to dearchelseapodcastmail.com Find full video episodes of Dear Chelsea on YouTube by searching earchelseapod. Dear Chelsea is edited and engineered by Brad Dickert Executive Producer Kathryn Lawrence. And be sure to check out our merch@chelsea handler.com.

You know that feeling when you come home late from work and those puppy dog eyes just pierce right through your soul? Yep, we've all been there. Pet parent guilt is real and completely normal. That's exactly why Hill's Pet Nutrition exists. They understand that being a pet parent means being human. Hill's science led nutrition helps you give more love than humanly possible. Whether it's those long work days or trying to balance attention between multiple pets. Hill's Pet Nutrition gets it because you're only human. There's Hills. Science does more Ready to let go of the guilt? Find the right [e-mail] iheart that's hillspet.com iheart you know what's not fun? Waking up at 2am drenched in sweat. Been there.

That's why I started using pod 5 from 8 sleep and let me tell you, it is a game changer. It's designed with women's help in mind, especially for those of us dealing with hot flashes. Pod 5 is this genius smart mattress cover that fits over any bed and pulls your body before a hot flash can mess with your sleep. And when I need an extra relief I just tap the bed or use the app to activate hot flash mode. 30 minutes of instant cooling. It's like having a personal climate concierge. It's clinically proven to reduce hot flashes by over 50% and I genuinely sleep deeper and wake up feeling way more refreshed. I love that it's a non medical solution, but it's backed by real data and it feels totally natural. Anyone who listens to this podcast knows that I would like to sleep in a refrigerator and now I can. And if you sleep with a partner, Pod 5 cools each side of the bed independently. So no more kicking someone out for being a human furnace. You both get your perfect temperature from 55 degrees to 110 degrees.

Go to 8sleep.com Chelsea use code Chelsea and get up to $700 off pod 5. You can try at risk free for 30 days. Trust me, better sleep starts here. Since I want the absolute best for my chow chow Doug, I am making the switch to Ollie. Your dog's well being starts with their food and that's why Ollie delivers fresh human grade food that your dog will love. So head to ollie.com Chelsea and use code Chelsea to get 60% off your welcome kit when you subscribe today. Plus, they offer a happiness guarantee on the first box, so if you're not completely satisfied, you'll get your money back. That's Ollie o l l I-e.com Chelsea and enter code Chelsea to get 60%.

Off your first box.

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[Chelsea Handler]

If you're looking.

For a wine that's not just delicious but also a total crowd pleaser, let me introduce you to Josh Sellars. This California wine brand has over a dozen award winning wines. From crisp Sauvignon Blancs to velvety Merlots. Josh Sellers has the perfect wine for every occasion. Serving up a juicy steak at your next barbecue. Their Cabernet Sauvignon is the perfect pairing. Unwinding with friends after a long week, you can't go wrong with their Pinot Grigio. With so many delicious wines to choose from, Josh Sellers has something for everyone. Josh Cellars is a proud sponsor of Dear Chelsea. Visit www.joshcellars.com Chelsea and join the Wine Club to get 20% off. Please drink responsibly.

This is an I Heart podcast.