Dear Chelsea – Minisode: Gold-Star Gay with Chelsea + Catherine (April 10, 2026)
Podcast: Dear Chelsea | Host: Chelsea Handler with Catherine Law

Episode Overview

This minisode centers on listener advice about relationships and insecurities, with a primary focus on queer women’s experiences. The highlight is a candid, supportive conversation with a lesbian caller grappling with insecurities while dating a bisexual woman—unpacking themes of trust, confidence, and the impact of cultural narratives. Chelsea Handler and Catherine Law bring their signature mix of compassion, realism, and humor, discussing everything from hiring women for odd jobs to the perils of men in open-toed shoes.

Key Discussion Points & Insights

1. The Power of Women Hiring Women (04:28)

• Trend Discussion: Catherine brings up an online movement promoting women hiring women for jobs ranging from dentistry to handywork—companies like "Rent a Butch" and "Not a Man Solutions."
  • “Why would I hire a man when I can just hire a woman to do this? … Even companies that are like Rent a Butch, where you can hire a woman to come and install your shelves or whatever.” – Catherine (04:29)
• Personal Choices: Both hosts share they've shifted their own service providers to women.
  • “My dentist is a woman. My gynecologist is a woman. My dermatologist is a woman.” – Katherine (05:07)
• Spending as Activism:
  • “We’re voting with our dollars whenever we spend a dollar. So like, let’s spend it with women.” – Catherine (05:51)

2. Listener Update: Alyssa and Dog-in-Bedroom Compromise (06:16)

• Alyssa, a previous caller, updates that after sharing the podcast with her boyfriend (who’d opposed sleeping with their dog), he realized he’d been unreasonable. They now compromise by leaving the bedroom door open for the dog.
• Alyssa feels happier with more work-from-home days to spend quality time with her pet.
  • “On top of that, I got a new job a couple of weeks ago and I’m able to work from home Mondays and Fridays, which gives me much more one-on-one time with my dog than I had before.” – Alyssa (06:38)
• Light-heartedly, Chelsea and Katherine discuss Chelsea’s dog Doug, whose coat is getting lighter due to less sun exposure in Whistler.

3. Main Caller: Kristen’s Relationship Insecurities (10:23–26:49)

Context:
Kristen (32), a lesbian who came out at 23, seeks advice about insecurities while dating a bisexual woman. Her fears stem from being previously cheated on by a bisexual partner and from growing up gay in the South, where stigma is rife.

Key Issues Discussed:

• Fear of not being “enough” for a bisexual partner—worried she cannot offer what a man can.
• Wondering whether insecurities are rooted in trauma or real relationship “red flags.”
• The challenge of not letting professional problem-solving (as a PhD and advocate) spill into personal life.

Chelsea & Catherine’s Guidance:

• Insecurities ≠ Intuition:
  • “That negative talk in our brains… that’s not your intuition. That’s just your negative narrative.” – Katherine (12:59)
  • “There’s nothing you can do to control anybody else’s behavior. The only person’s behavior you’re in control of is your own.” – Katherine (12:39)
• Trust and Transparency:
  • A partner’s honesty in choosing you is a positive, not a negative.
    • “She was honest about being with someone else and then choosing you to be with. That’s not a negative… that’s being transparent.” – Chelsea (13:45)
• Gay Community & Internalized Negativity:
  • Kristen describes pervasive cultural messages that gay relationships are doomed to fail, which amplify insecurities.
    • “You are taught that there is no healthy relationship for us…so whenever something negative happens, you go ‘oh, it’s because of this.'” – Kristen (14:00)
• Dealing with Overthinking:
  • Journaling feelings and triggers is suggested as a way to break patterns.
    • “When you do have these thoughts, write it down… When you get up, be like, ‘I’m a fucking badass.’” – Katherine (18:58)
• Self-Fulfilling Prophecy:
  • “When you think like that and you act like that, it’s almost like you could kind of create that situation.” – Katherine (21:04)
  • “Nobody wants to be with somebody who’s insecure about being with them. It’s not a turn on.” – Katherine (19:30)
• Dating Bisexual Partners:
  • Reassurance that worries about not being “enough” for a bi partner are unfounded and comparable to arbitrary worries like “what if he meets a brunette?”
    • “The penises you can buy at the store… that’s like me dating someone and being like, what if he meets a brunette?” – Katherine (20:01; 20:27)
    • “It’s silly because he’s dated brunettes before.” – Katherine (20:29)
• Choosing What to Focus On:
  • “If I’m wasting my attention on something, it better be like marching in the street… I don’t want to waste it on something that’s not real.” – Kristen (24:38)
  • “Focus your attention and intention on the things that are good in your life and all of the things that you can control.” – Katherine (25:49)
• Memorable Motivational Advice:
  • “I’m a fucking badass. I’m in a happy relationship. I have a great job. I’m gonna go and kick ass today!” – Katherine (18:58)
  • “You have all these good things in your life, like fucking focus on them for sure.” – Katherine (26:43)

4. Quick Listener Letter: Footwear Rage & Veterinary Microaggressions (29:25)

• Dr. Amy (a vet and small goat farmer) is disgusted by clients’ open-toed footwear, compounded by microaggressions as a female vet.

• Chelsea & Catherine’s Solution:

  • Suggest putting a sign at the vet practice: “Full footwear required. No open-toed shoes.”
    • “There’s nothing wrong with putting that on a sign… We appreciate full foot coverage. So it’s more of a suggestion.” – Katherine (30:55–31:15)
  • Suggest letting dog owners do the “coaxing” of nervous dogs out from under chairs.

• Chelsea’s Take on Flip-Flops:

  • “Whoever came up with flip flops needs to get sued. And I should be the one.” – Katherine (32:31)
  • Witty riff on men’s willingness to wear flip-flops, no matter the climate.

Notable Quotes & Memorable Moments

• “You’re voting with your dollars of what you want to see more of. So voting for women.” – Catherine (05:59)
• “Yes, I love that. First of all, if you’re a woman, you want a female doctor. I mean, that just makes more sense.” – Katherine (05:39)
• “I know I’m a catch. I have a solid career. I have a PhD and actively work on equality in Arkansas, of all places.” – Kristen (from email, 11:55)
• “I don’t want to be that—I can’t compete. … That’s like me dating someone and being like, what if he meets a brunette?” – Katherine (20:19–20:27)
• “You don’t have time for this old story. Like, that’s not helping you.” – Katherine (16:54)
• "Nobody wants to be with somebody who's insecure about being with them. It's not a turn on. Nobody likes that." – Katherine (19:30)
• "If I’m wasting my attention on something, it better be like marching in the street. You know what I mean? I don’t want to waste it on something that’s not real." – Kristen (24:38)
• "Whoever came up with flip flops needs to get sued. And I should be the one." – Katherine (32:31)

Timestamps for Important Segments

• [04:28] – Women hiring women: Catherine’s anecdote on "Rent a Butch" and pro-woman service trends.
• [06:16] – Update from previous caller Alyssa (dog-in-bedroom compromise).
• [10:23] – Main advice segment: Kristen’s question on relationship insecurities with a bisexual partner.
• [12:03-26:49] – Deep-dive advice for Kristen, unpacking trauma, internalized stigma, and confidence in queer relationships.
• [29:25] – Dr. Amy’s letter about men in open-toed shoes and microaggressions in veterinary medicine.
• [32:31] – Chelsea and Catherine riff on flip-flops and societal footwear faux pas.

Summary Takeaways

• Empowerment & Boundaries: Vote with your dollars, support women, assert your needs—whether in healthcare or relationships.
• Relationship Wisdom: Differentiate between intuition and insecurity; don't let past trauma or internalized narratives cloud present joy. Trust transparency, not obsessive overthinking.
• Practical Tools: Journal triggers, talk to yourself kindly, and practice intentionality—focus on what you can control.
• Humor & Relatability: Chelsea and Catherine’s lighthearted takes keep things grounded—even when decrying flip-flops and men’s feet.

For further advice, the hosts encourage listeners to write in to dearchelseapodcast@gmail.com.