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)

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.

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.

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.

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 |

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

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.

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.