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

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

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.

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)

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)

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.” |

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

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.

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.