Minisode: Type Ho Positive with Chelsea + Catherine

Summary

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

Podcast: Dear Chelsea
Hosts: Chelsea Handler & Catherine Law
Date: November 28, 2025
Episode Type: Minisode (Listener Advice)

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Episode Overview

In this “Type Ho Positive” minisode, Chelsea Handler and Catherine Law dive into two listener dilemmas, offering their signature blend of humor, blunt honesty, and empathetic advice.

• First, a pained friend writes in about her friend’s engagement to a controlling, regressive partner.
• Second, a gay male listener seeks advice about desires for non-monogamy and waning sexual dynamics in his relationship.
  Throughout, Chelsea and Catherine champion honesty, self-respect, and putting female (and personal) agency front and center—while keeping it very real.

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Key Discussion Points & Insights

1. Follow-Up: The Friend Marrying a “MAGA Yokel”

[03:17 - 06:54]

• Background: Carly wrote in previously about her friend “H” who’s dating an ultra-conservative, controlling man who wants her “barefoot and pregnant” and is already talking prenups. The friend group tried interventions, but now H is engaged and moving to Alabama.

• Carly’s Dilemma: “How do I keep it together and act supportive when I’m heartbroken and don’t believe in this match?”

Chelsea & Catherine's Reactions:

• Catherine’s Take ([04:27]):

  “Honestly, if someone like that, who’s basically telling her not… she’s giving her life away to some man… If there’s any way to put your foot down, this is it. That I can’t be in it. 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.”

• On Attending the Wedding:

  “No, I wouldn’t. That friendship is over. She’s gone. She’s not going to be allowed to talk to her friends after a certain amount…” – Catherine ([05:25]) “Men that are that controlling often are like, well, no, you can’t talk to these friends.” – Chelsea ([05:35])

• Giving a Wake-Up Call:

  “Hopefully your lack of participation in her wedding will be a wake up call.” – Catherine ([05:58])

• Personal Experience:
  Chelsea relates ([06:26]) that, for her, when all the people who loved her voiced concern about her partner, it became the catalyst for change:

  “Maybe I should leave because all these people are upset for me… And two weeks later, I snapped out of it and I was like, oh, wait, that was terrible.”

Key Insight:

• Sometimes, refusing to support a friend’s relationship can be a necessary act of love and self-respect, even if it risks the friendship. Interventions may not work, but withdrawal of support can sometimes spark a realization.

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2. Listener Jeff: “Am I a Hoe or Just a Guy?”

[11:53 - 20:16]

• Jeff’s Situation:
  In a monogamous relationship (9-10 months), Jeff realizes monogamy might not suit him. Their sex life has fizzled, with unmet desires for a more dominant partner. He develops a crush on a bartender but feels guilty and wonders if having such urges makes him “a hoe.”

On Being “Hoe Positive”:

• Catherine:

  “You’re a gay man, so everything you’re feeling is completely natural.” ([13:37]) “We’re hoe positive. You’re in a safe place… Safe hoe positive place.” ([13:59])

How to Approach Non-Monogamy:

• Catherine presents two options ([14:44]):

  “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.”

• Jeff’s Integrity:

  “I never want to become the cheater. I’ve never cheated on anybody in my life. I don’t want to start today.” ([14:54])

Having The Conversation:

• Cheating vs. Honesty:

  “It’s more hurtful to be dishonest and deceptive… 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.” – Catherine ([17:59])

• Chelsea’s Input:

  “He didn’t shut it down… an ‘okay’ is like, all right, let’s revisit this later.” ([16:19]) “Being in a relationship with someone is all about experimenting, especially in the bedroom… things are still evolving.” ([18:22])

• On Relationship Communication:

  “You’re at a great place in your relationship to start having really honest conversations… That is also a sign of how long the relationship can last…” – Catherine ([19:08])

• Advice on Openness Formats:

  “What are the rules? Do you want to know? Like, are we gonna be open and just not tell each other, or are we gonna be open and tell each other? It’s probably healthiest to be open and not divulge every single detail.” – Catherine ([17:01])

Humorous Send-Off:

• Catherine (wishing Jeff well):

  “And then hopefully you can go fuck that guy that you want to fuck.” ([20:00])

• Chelsea:

  “Please report back when you fuck that guy.” ([20:02])

Key Insight:

• Openness isn’t shameful; it’s often healthier to be upfront than to deceive. Sexual and relational needs evolve—having the adult conversation is a mark of respect for both parties.

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Notable Quotes & Memorable Moments

| Timestamp | Quote | Speaker | |-----------|-------|---------| | 04:27 | “If there’s any way to put your foot down, this is it. That I can’t be in it. I’m so sorry, I love you so much, but this is breaking my heart and I cannot be involved in this wedding.” | Catherine | | 05:35 | “Men that are that controlling often are like, well, no, you can’t talk to these friends…” | Chelsea | | 06:26 | “When… all these people who I knew all loved me were all telling me the same thing about this person… two weeks later I, like, snapped out of it…” | Chelsea | | 13:59 | “We’re hoe positive. You’re in a safe place… Safe hoe positive place.” | Catherine | | 14:54 | “I never want to become the cheater. I’ve never cheated on anybody in my life. I don’t want to start today.” | Jeff | | 16:28 | “He didn’t shut it down right away. I mean, an okay is like a. All right, like, let’s revisit this later.” | Chelsea | | 17:59 | “It’s more hurtful to be dishonest and deceptive… Give him enough credit, have enough respect for him…” | Catherine | | 19:08 | “You’re at a great place in your relationship to start having really honest conversations… That is also a sign of how long the relationship can last…” | Catherine | | 20:00 | “And then hopefully you can go fuck that guy that you want to fuck.” | Catherine | | 20:02 | “Please report back when you fuck that guy.” | Chelsea |

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Important Timestamps

• 03:17: Introduction to Carly’s update on her friend’s engagement
• 04:27 - 06:54: Deep dive: Should Carly participate in the wedding?
• 11:53: Listener letter from Jeff: struggles with monogamy, desire for openness
• 13:33: Jeff joins the conversation
• 14:05 - 19:56: Candid talk about how to approach opening up a relationship
• 20:00: Hosts’ cheeky goodbye to Jeff

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Tone & Language

The tone is frank, empathetic, unapologetically honest, and laced with comedic moments. Chelsea and Catherine provide advice that’s both practical and emotionally intelligent, encouraging listeners to act with integrity—even when it’s difficult. Their rapport with Jeff, in particular, is warm and supportive, reinforcing “hoe positivity” as a No-Judgment Zone.

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Summary Takeaway

This minisode of Dear Chelsea tackles thorny friendship and relationship dilemmas with sharp wit and a deeply supportive, honest approach. Whether it’s standing against a friend’s bad marriage or navigating the complexities of sexual needs in a long-term relationship, the advice is clear: speak up for what you believe, respect your needs and those of others, and trust in open, brave communication—even (especially!) when it’s hard.

Transcript

[Chelsea Handler]

This is an I Heart podcast. Guaranteed human.

[Kathryn]

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[Pandora Jewelry Announcer]

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[Kathryn]

If you thought season two of Sniffy's Cruising Confessions was spicy, buckle up. Season three is here and hosts Gabe Gonzalez and Chris Patterson Rosso are going deeper than ever with bold new conversations, fresh guests and unfiltered takes on queer sex and cruising. This season they're also looking out for the community covering smart cruising in a chaotic world, including information on prep and yes, they're calling call in segment is getting even hotter, and they'll react to your wildest cruising confessions on air. No pressure. Tune in to Sniffy's Cruising Confessions, sponsored by Healthy Sexual from Gilead Sciences, with new episodes every Thursday on the iHeartRadio app or wherever you get your podcasts. Hey, I'm Steffi.

[Chelsea Handler]

I go big for the holidays, so.

[Kathryn]

I'm going to Famous footwear. With over 800 stores, you're never far from the perfect gift, so make your list and make it famous. Buy one pair. Get one half off at Famous Footwear or famous.com, so some exclusions apply. Hi, Kathryn.

[Chelsea Handler]

Hi, Chelsea. Hi.

[Kathryn]

What are we doing?

[Chelsea Handler]

We're doing a minisode today.

[Various Advertisers/Promoters]

Okay.

[Kathryn]

Today is a. Welcome to our minisode.

[Chelsea Handler]

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. And it's amazing that I remember, but I do once.

[Kathryn]

Once.

[Chelsea Handler]

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, so how do I keep it together?

[Kathryn]

No, no.

[Chelsea Handler]

Yes. You know the question? How am I supposed to be happy for her? She's genuinely so happy, and I want to be, but it just doesn't come naturally.

[Kathryn]

Carly, I just think you have to say I can't support this marriage. Honestly, if someone like that, who's basically telling her 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 gonna 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 it. 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.

[Chelsea Handler]

Yeah. Now would you even go to the wedding?

[Kathryn]

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.

[Chelsea Handler]

That's probably true.

[Kathryn]

So what's the point?

[Chelsea Handler]

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.

[Kathryn]

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.

[Chelsea Handler]

Yeah. And you know what? Sometimes weddings get canceled.

[Kathryn]

So, yeah, you should listen to your friends when they know better. Yes, they 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.

[Chelsea Handler]

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 was terrible.

[Kathryn]

Yeah.

[Chelsea Handler]

All right, Carly, wish you the best of luck. And you have some hard conversations ahead.

[Kathryn]

Of you and they told her how they felt. Oh yeah.

[Chelsea Handler]

Yeah.

[Kathryn]

Okay.

[Chelsea Handler]

All right. Well, we'll take a quick break and be back with a question.

[Kathryn]

Okay.

[Annabe Sofas Announcer]

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[Pandora Jewelry Announcer]

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[Kathryn]

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[Chelsea Handler]

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 it's. 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 be possibly be open one day? Jeff.

[Kathryn]

Hi. How are you?

[Jeff (Caller/Guest)]

Oh, I'm so good. This is like the best day of my life right now. You have no idea.

[Kathryn]

Oh, 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?

[Jeff (Caller/Guest)]

So can I just also first say that I don't say the word hoe in a malevolent way?

[Kathryn]

No, me neither.

[Knix Announcer]

Love a hoe.

[Kathryn]

Me neither. I'm a hoe too. Okay, thank you.

[Jeff (Caller/Guest)]

All the time.

[Kathryn]

I get it.

[Jeff (Caller/Guest)]

That's not how I mean it. So.

[Kathryn]

No, no, no, no, you don't have to explain yourself. We're hope positive you're in a safe place right now. Safe hoe positive place.

[Jeff (Caller/Guest)]

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.

[Kathryn]

It is.

[Jeff (Caller/Guest)]

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.

[Kathryn]

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.

[Jeff (Caller/Guest)]

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.

[Kathryn]

That's your answer.

[Jeff (Caller/Guest)]

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?

[Kathryn]

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 it's. Hopefully you're hoping for it to be long term. It is long term already. How long have you guys been together?

[Jeff (Caller/Guest)]

Probably nine, going on ten months, so.

[Kathryn]

Oh, ten months. Okay. Okay, copy that. Okay, so what you. But you're hoping to be in a long term relationship?

[Jeff (Caller/Guest)]

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 will 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.

[Kathryn]

But don't you want to pursue this other guy at work that you're talking About.

[Jeff (Caller/Guest)]

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 just don't want to do it.

[Chelsea Handler]

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.

[Kathryn]

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.

[Jeff (Caller/Guest)]

Yeah, I agree. I think it should be. At least that's, you know.

[Kathryn]

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 gonna be open and just not tell each other, or are we gonna 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, you know, without making it about a. 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 wanna make sure you're comfortable with this and just come to an agreement where you're both having input.

[Jeff (Caller/Guest)]

Okay, Yeah, I think I could do that.

[Kathryn]

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 gonna be that disruptive, especially since you already introduced the topic.

[Jeff (Caller/Guest)]

Yeah, I suppose so. I just. I do worry about hurting his feelings, I guess. Doesn't seem warm to it.

[Kathryn]

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.

[Chelsea Handler]

Yeah. And it can be an ongoing conversation. Like, he doesn't have to, like, say yes after the first conversation. They both go out and sleep with.

[Pandora Jewelry Announcer]

That's.

[Chelsea Handler]

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.

[Kathryn]

Yeah. So now he calls her Chelsea, which is really weird in bed, you know, and unprofessional workplace.

[Chelsea Handler]

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.

[Kathryn]

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 gonna move around in this relationship, you're only gonna, 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.

[Jeff (Caller/Guest)]

Okay. Yeah, I think you're right. Maybe I'm kind of, like, anticipating the worst maybe. Which is something I. Yeah.

[Kathryn]

So stop that.

[Jeff (Caller/Guest)]

Professionally doing.

[Kathryn]

Stop that. Right, right.

[Jeff (Caller/Guest)]

Okay.

[Various Advertisers/Promoters]

Okay.

[Kathryn]

Good, Good.

[Jeff (Caller/Guest)]

All right.

[Chelsea Handler]

Thanks, Jeff.

[Kathryn]

And then hopefully you can go fuck that guy that you want to fuck.

[Various Advertisers/Promoters]

Yeah.

[Chelsea Handler]

Please report back when you fuck that guy.

[Jeff (Caller/Guest)]

All right. Yeah, no, I'll definitely follow up with you.

[Chelsea Handler]

I mean, maybe your boyfriend wants to go fuck that guy with you. Who knows? Yeah.

[Kathryn]

Yeah. This could get why actually, great idea. Yeah. Love it.

[Jeff (Caller/Guest)]

Yeah. I mean, anything's possible. Sure.

[Chelsea Handler]

All right.

[Pandora Jewelry Announcer]

Thanks, Jeff.

[Kathryn]

Bye, Jeff.

[Jeff (Caller/Guest)]

Thanks so much. Jason Miu. Take care.

[Kathryn]

Okay.

[Chelsea Handler]

Yeah. All right, well, we're good to go on wrap.

[Kathryn]

Okay. And we're wrapped on another episode of Dear Chelsea. Thanks guys for listening. Make sure you go to chelseahandler.com to find tickets for my standup shows. Come see me. Come see me live. It's going to be a good time, guys.

[Chelsea Handler]

Bye. Excellent.

[Kathryn]

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 for free forum I will be on the High and Mighty Tour.

[Chelsea Handler]

Do you want advice from Chelsea? Write into dearchelseapodcastmail.com Find full video episodes of Dear Chelsea on YouTube by searching eercelsea pod. Dear Chelsea is edited and engineered by Brad Dickert Executive Producer Katherine Law and be sure to check out our merch@chelsea handler.com.

[Various Advertisers/Promoters]

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[Chelsea Handler]

This holiday with the new Whim Sound Smart Speaker.

[Various Advertisers/Promoters]

Get high resolution audio with a 1.8 inch touchscreen. Smart control and modern design in one powerful speaker for just 299.

[Chelsea Handler]

From Quiet Mornings to lively holiday gatherings.

[Various Advertisers/Promoters]

Wind sound makes every moment sound better and feel better too. Get the gift of the season for the music enthusiast in your life or for yourself. Whim sound Beautifully designed, effortlessly connected. Shop now at Amazon and search whim sound.

[Chelsea Handler]

That's W I I M S O.

[Various Advertisers/Promoters]

U n d What a matchup we got, y'.

[Jeff (Caller/Guest)]

All.

[Various Advertisers/Promoters]

This is that classic HBCU vibe. Non stop action. The band is rocking and the crowd lit. Chance echo drum beat, everybody showing that spot. A game like this, yeah, it calls for an ice cold Coca Cola. Ah, crisp and refreshing. That's a game changer right there. Yeah, that taste always hits the right note. Just like the band at halftime. And just like that, we're back at it. Passionate fans, school colors everywhere, and an ice cold Coca Cola. That's a winning combo. No matter what the sport, no matter the yard. Everybody knows fan work is thirsty work. So grab a Coca Cola and keep that HBCU pride going. Janice Torres here, and I'm Austin Hankwitz. We host the podcast Mind the Business, Small Business Success Stories, produced by Ruby Studio in partnership with Intuit QuickBooks.

[Chelsea Handler]

We're back for season four to talk.

[Annabe Sofas Announcer]

To some incredible small business owners.

[Various Advertisers/Promoters]

The big thing about working at tech is that it's ever evolving, ever changing. Everyone's a rookie. That's how fast the industry is changing. So what I'm really excited about is to be part of that change. So listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

[Chelsea Handler]

This is an iHeart podcast. Guaranteed Human.