Dear Chelsea – Minisode: Not Interested in Being Exclusive (October 31, 2025)
Podcast: Dear Chelsea
Hosts: Chelsea Handler and Katherine Law
Episode Theme: Relationship Updates, Dating Non-Exclusivity, and Listener Q&A
Date: October 31, 2025
Episode Overview
This minisode, co-hosted by comedian and author Chelsea Handler and her producer Katherine Law, blends listener updates and relationship advice with the signature unfiltered humor and candor the show is known for. The episode covers updates from past listeners, guidance for navigating non-exclusive dating, and a discussion on the ethical dilemma of owning a Tesla. Throughout, Chelsea and Katherine offer witty, practical, and empathetic insights while sharing their personal takes.
Key Discussion Points and Insights
1. Tech Confusion and Substack 101
[02:27–03:22]
- Chelsea gives Katherine a crash course on Substack, explaining its function as a “fancy word for a newsletter,” often behind a paywall and possibly featuring podcasts.
- Katherine laments unwanted emails, “All I do is unsubscribe, unsubscribe, unsubscribe.” (02:47)
- Chelsea explains, “It’s sort of like a new, cool version of a newsletter that seems salesy.” (03:15)
- Light banter about feeling out of touch with technology.
2. Listener Updates: Love & Family
[03:28–08:21]
A. Elisa’s Relationship Evolution
[03:28–05:26]
- Elisa gives an update about a past relationship question: she found love with the bartender she once dated casually, navigated a breakup, got back together (now long-distance), and reflects on her happiness and independence.
- Chelsea jokes, “At least she doesn’t have to go out and have casual sex anymore. Although maybe she wants to while she’s got this, like, boyfriend back home.” (05:02)
- Both hosts admit they can’t remember the exact advice given but praise Elisa’s personal growth and self-dating.
B. Family Drama Follow-Up
[06:09–08:21]
- Update from a listener cut off by a sister-in-law (not invited to niece’s birthday).
- Listener followed Chelsea's advice to confront the issue directly and learned the rift was about not discussing birthday plans in person.
- Chelsea calls it “so stupid.” (07:54)
- Katherine compares dealing with petty grievances to “dealing with a terrorist on the other end of the spectrum.” (07:58)
- Final advice: “You can only be responsible for how you’re showing up. Show up with light and love... If she wants to be grumpy, let her be grumpy and that’s fine.” —Katherine (08:06–08:16)
3. Listener Q&A: Modern Dating & Tesla Dilemma
[11:40–15:09]
A. Is Dating Multiple Men at Once a “Bitch Move”?
[11:40–13:23]
- Mag, a 20-something listener, asks if there's anything wrong with dating several people at once.
- “Is this a bitch move? If not, why do I feel bad about it?” —Mag (12:45)
- Chelsea: “No! As long as everybody knows, you’re in the clear. Like, ‘I’m not exclusive. Not interested in being exclusive right now.’” (12:58)
- Katherine: “Absolutely, do not! There’s nothing wrong with that.” (13:09)
- Chelsea: “Who’s got time to date one person at a time anymore? Keep it coming, keep it coming.” (13:14)
- Both stress honesty and non-exclusivity until it feels right.
B. Should I Ditch My Tesla Because of Elon Musk?
[13:23–15:09]
- Listener Elsie shares her internal conflict about driving a Tesla given Elon Musk’s politics, calling it a “self-driving moral dilemma.” (13:29)
- Katherine: “I ditched mine. My sister’s waiting for her lease to be up... I feel like you have to stand on principles. He doesn’t deserve your money.” (14:01)
- Chelsea and Katherine mock the cult-ish Cybertruck and discuss the vehicle recalls.
- Brad, the sound engineer, is called in as a “straight man” for a car-guy opinion but admits, “Because it’s a Tesla and I don’t really care.” (14:57)
- Advice: If possible, ditch the Tesla; if not, at least reconsider future support.
Notable Quotes & Memorable Moments
- “We have to have Carlos go in and, like, unsubscribe from everything.” —Chelsea (02:53)
- “I’ve never felt this way for someone and I’m so comfortable with him for now. There are parts of living alone in the city that I love and I shared with you before that I have a really good vibrator, so I’m good until we can figure it out.” —Listener Elisa (04:46)
- “Catherine is having an inter office and inner office affair with her husband Brad who is our sound engineer… Thank you Brad for remembering. Yes, that sounds like it tracks.” —Chelsea (05:46)
- “When you’re dealing with people holding onto very small, petty things... it’s like dealing with a terrorist on the other end of the spectrum.” —Katherine (07:58)
- “Who’s got time to date one person at a time anymore? No, keep it coming. Keep it coming.” —Chelsea (13:14)
- “He doesn’t deserve your money.” —Katherine on Elon Musk/Tesla (14:16)
- “Because it’s a Tesla and I don’t really care.” —Brad Dickert, Sound Engineer (14:57)
- “Way to misrepresent yourself and this podcast, Brad.” —Katherine (15:00)
Important Timestamps
- Substack Explainer: 02:27–03:22
- Elisa’s Relationship Update: 03:28–05:26
- Sister-in-Law Family Drama: 06:09–08:21
- Modern Dating Multiple People (Mag’s Question): 11:40–13:23
- Tesla/Elon Musk Dilemma: 13:23–15:09
Episode Tone & Style
Breezy, sharp, and irreverent; Chelsea and Katherine maintain their trademark wit and honesty throughout, tackling listener questions with empathy punctuated by snarky asides and banter, making the episode as entertaining as it is helpful.
This episode is perfect for anyone struggling with relationship boundaries, feeling “behind” in the modern dating world, or looking for validation that their struggles with tech (and Tesla) are shared by others.