Dear Chelsea – Minisode: "Single White Female with Chelsea + Catherine"

Date: September 19, 2025
Hosts: Chelsea Handler & Kathryn Law
Guests: Alexis & Shaka Khan (mother/daughter callers)

Episode Overview

In this candid and humorous minisode, Chelsea Handler and her co-host Kathryn Law tackle listener questions about dating and female friendship dynamics. The main focus is a heartfelt conversation with a mother-daughter duo, Alexis and Shaka Khan, who share personal struggles with toxic female friendships and the peculiar experience of attracting "Single White Female"-type friends. Chelsea offers her trademark unfiltered advice, encouraging boundaries, discernment, and embracing one's true self.

Key Discussion Points & Insights

1. Dating Updates: Following Up on Carly (03:10–04:27)

• Kathryn shares an email update from Carly, a previous caller who was struggling with situationships and had feelings for a coworker.
• Carly took the advice to express her feelings, but things did not work out with the coworker. She’s now dating for fun, has more agency, and is focusing on career, travel, and friends-with-benefits.
• Chelsea and Kathryn discuss the importance of not believing in "the one" soulmate concept.
  • Notable Quote:
    • Chelsea: “Let’s all just get out of the idea that there’s one person out there for us… that’s just so silly. That’s impossible with—there’s 9 billion people on the planet almost now.” (04:28)

2. Advice Session: Toxic Female Friendships (06:28–24:15)

Alexis’ Letter & Shaka Khan’s Experience (06:28–08:05)

• Alexis writes in about her mother’s recurring issue with female friends who are draining, dramatic, or even stalker-like.
• Shaka Khan joins the call, confirming the issue and sharing shocking anecdotes (e.g., a “friend” copying her car, trips, and stalking her online and in person).
  • Notable Quote:
    • Shaka: “She bought her entire family a trip. To Tulum, including like, a single white female.” (08:05)
    • Shaka (reading a message): “‘You may have blocked me on every social media platform, but if you don’t think that I know what you’re doing, you’re delusional. I will spend eternity plotting your just rewards. C U N T.’” (08:31)
  • Chelsea: “That’s a different level. That’s a stalker. Psycho.” (09:04)

Analyzing the Pattern (09:45–10:56)

• Chelsea probes whether this pattern has repeated with multiple women.
• Shaka discusses having to “interview” potential new friends because of repeated experiences with unhealthy, enmeshed relationships.

Developing Boundaries in Friendships (10:56–13:22)

• Shaka notes she now has a “spidey sense” for draining people and is more discerning as she’s gotten older.
• Chelsea encourages building boundaries and focusing on strength and autonomy in friendships.
  • Notable Quote:
    • Chelsea: “You just have to have a little bit more discernment about who you let into your circle. And that’s great, because you have to set up boundaries. And you, like you said, when you’re in your 50s, those boundaries are much easier to set because it’s not like an option. It’s almost like a mandate.” (12:21)
    • Chelsea: “You’re not gonna allow any more fruitcakes into your life… be very clear at the outset.” (12:27)
• Shaka wonders if strong, well-boundaried women are out there. Chelsea insists they are.
  • Notable Quote:
    • Chelsea: “Yes, they are! Of course they are. It’s like discounting men. You can’t discount all men, only discount most of them. You know what I mean?… But no, there are women out there that are like that.” (13:00)

Practical Tips for Making Friends (19:46–21:28)

• Kathryn suggests finding group activities (like book clubs) instead of seeking one-on-one friendships, to naturally become part of existing, healthy groups.
• Shaka recounts joining a new group and being puzzled when her affectionate nickname for people (“lovey”) was instantly adopted by others—demonstrating her magnetic influence.
  • Chelsea’s Strategy:
    • Floats in and out of different friend groups rather than being enmeshed. Prefers being a “periphery” friend and recommends the same for Shaka.
      • “I like to be the kind of outsider of friend groups because I like to float around.” (20:30)

Managing Unhealthy Attachment & Stalking (21:45–24:10)

• Shaka describes how unsettling it is being stalked by women, including concerns for her own safety.
• Kathryn advises ignoring toxic individuals unless safety is at risk, then seek legal action (e.g., restraining order).
• Alexis: Thinks her mother attracts others insecure in their own identity, who then ape her style and choices.
• Chelsea reaffirms: Don’t change your personality to avoid attracting these people, just exercise more caution letting new people close.
  • Notable Quotes:
    • Shaka: “At some point now, in my 50s…I’m embracing who I am. And I don’t give two shits about what people are thinking or doing.” (23:20)
    • Chelsea: “You shouldn’t change who you are. You should just be like what we’ve already discussed, which is more discerning about letting people get close to you… Don’t go all in right away.” (23:36)
    • Kathryn: “If it doesn’t feel good for you, then it doesn’t. It’s not good. And you don’t have to take that on…” (23:58)

Memorable Moments & Quotes

• “Your daughter thinks all of your friends are assholes.”
  — Chelsea Handler, directly to Shaka Khan (06:57)

• “They start just, like, wearing the same clothes, doing their hair the same… At first I thought it was a compliment, and then the more times I noticed this is happening, I’m like, okay, something is up. Like, this is not normal behavior.”
  — Alexis (22:49)

• “Maybe the universe knew I was gonna get some dog-shit women, and they gave me a daughter, you know?”
  — Shaka Khan (21:37)

• “It’s not like you need a gaggle of girlfriends… It’s not a fucking emergency.”
  — Chelsea Handler (18:49)

Timestamps for Major Segments

• 03:10 – Carly’s update on situationship and new, fun approach to dating
• 04:28 – Discussion about the “soulmate” myth
• 06:28 – Introduction of Alexis & Shaka Khan and her recurring issues with unhealthy friendships
• 08:05 – Shaka’s story of being stalked and mimicked by a “friend”
• 10:20 – Strategies to vet new friends and set boundaries
• 12:21 – Chelsea’s advice about boundaries post-50 and discernment
• 13:00 – Chelsea affirms there ARE good women out there
• 19:46 – Kathryn suggests joining groups instead of seeking single friends
• 20:30 – Chelsea explains her “floater” friendship strategy
• 21:37 – Shaka on being grateful for her daughter as “the universe’s fix”
• 23:36 – Final advice to embrace oneself, but be selective letting people in
• 24:13 – Show wraps up with thanks and goodbyes

Conclusion

This lighthearted yet meaningful minisode is classic Dear Chelsea: a mix of sharp honesty, personal storytelling, and empowering advice about friendship, boundaries, and living authentically. The hosts tackle heavy topics with humor, reinforce the importance of self-respect and discernment in relationships, and remind listeners: you don’t have to settle for “dog-shit” friends or believe in just one soulmate.

For those who haven't listened:
This episode will especially resonate with anyone who's navigated tricky friend dynamics, struggled with "energy vampire" relationships, or wondered if it's okay to float in and out of social circles. Chelsea’s advice champions owning your magnetism while keeping clear boundaries, offering both catharsis and actionable tips—with plenty of laughs along the way.

Notable Quotes with Timestamps:

• “Let’s all just get out of the idea that there’s one person out there for us… that’s just so silly.” — Chelsea Handler (04:28)
• “She bought her entire family a trip. To Tulum, including like, a single white female.” — Shaka Khan (08:05)
• “That’s a different level. That’s a stalker. Psycho.” — Chelsea Handler (09:04)
• “You’re not gonna allow any more fruitcakes into your life.” — Chelsea Handler (12:27)
• “At some point now, in my 50s…I’m embracing who I am. And I don’t give two shits about what people are thinking or doing.” — Shaka Khan (23:20)
• “Maybe the universe knew I was gonna get some dog-shit women, and they gave me a daughter, you know?” — Shaka Khan (21:37)

Summary by Section:

• Quick, comedic update on dating and relationship advice
• Deep dive with a mother-daughter call on friendship stalkers
• Practical and motivational guidance for boundary-setting
• Relatable, lively, and full of signature Chelsea Handler humor