Minisode: Not Interested in Being Exclusive with Chelsea + Catherine

Summary

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

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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.

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Key Discussion Points and Insights

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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.

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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)

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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.

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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

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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.

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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.

Transcript

[Chelsea Handler]

This is an I Heart podcast.

[Chelsea Handler (Ad Voice)]

I used to wake up at 2am drenched in my own sweat. Not the cutest. Then I found pod 5 from 8 sleep and it changed everything. It's built with women's health in mind and helps with those brutal hot flashes. It is a smart mattress cover that cools your body before a hot flash hits. And when I need an instant relief, I just tap the bed to use the app to activate hot flash mode. It's clinically proven to reduce hot flashes by over 50% and it even cools each side of the bed independently. So go to 8sleep.com Chelsea use code Chelsea and get $350 off. You will thank me later since I.

Want the absolute best for my chow Chow Doug I am making the switch to Ollie. Your dog's well being starts with their food and that's why Ollie delivers fresh human grade food that your dog will love. So head to ollie.com Chelsea and use code Chelsea to get 60% off your welcome kit when you subscribe today. Plus they offer a happiness guarantee on the first box so if you're not completely satisfied, you'll get your money back. That's Ollie o l l I e.com Chelsea and enter code Chelsea to get 60% off your first box.

[Katherine]

From nursing and healthcare to business and IT, Rasmussen has a range of programs to fit your goals and passion for no matter what your day to day looks like. Rasmussen's programs allow you to balance school.

[Chelsea Handler (Ad Voice)]

With life while you pursue your degree. So if you're ready to pursue your.

[Katherine]

Education goals, Rasmussen is ready to help you take that next step. Head on over to Rasmussen. Edu and check out the opportunities waiting for you.

[Chelsea Handler (Ad Voice)]

Your future is a bright one.

[Katherine]

Rasmussen University can help you get there. You know that feeling when you come.

[Chelsea Handler (Ad Voice)]

Home late from work and those puppy dog eyes just pierce right through your soul?

[Katherine]

Yep, when you We've all been there.

[Chelsea Handler (Ad Voice)]

Pet parent guilt is real and completely normal. That's exactly why Hill's Pet Nutrition exists.

[Katherine]

They understand that being a pet parent means being human.

[Chelsea Handler (Ad Voice)]

Hill's science led nutrition helps you give.

[Katherine]

More love than humanly possible.

[Chelsea Handler (Ad Voice)]

Whether it's those long work days or.

[Katherine]

Trying to balance the tension between multiple pets. Hill's Pet Nutrition gets it because you're only human.

[Chelsea Handler (Ad Voice)]

There's Hills Science does more Ready to.

[Katherine]

Let go of the guilt.

[Chelsea Handler (Ad Voice)]

Find the right [e-mail] iheart that's hillspet.com iheart hi Katherine.

[Chelsea Handler]

Oh hello Chelsea.

[Chelsea Handler (Ad Voice)]

Hello.

[Chelsea Handler]

It's come to my attention that you need A primer on Substack.

[Katherine]

Well, yeah, it came to your attention. Cause I told you, Katherine, so that. I'm glad that it came to your attention. I do need a primer on substack.

[Chelsea Handler]

So I would imagine a lot of stuff.

[Katherine]

I have a lot of my friends.

[Chelsea Handler]

Yes, yes.

[Katherine]

And somehow I'm getting updates from substack, but I don't remember ever, like, joining. I like to limit my email intake.

[Chelsea Handler (Ad Voice)]

Do you know what I mean?

[Katherine]

I mean, it's too many emails from too many places that I don't even. I never signed up for. And all I do is unsubscribe, unsubscribe, unsubscribe.

[Chelsea Handler]

We have to have Carlos go in and, like, unsubscribe from everything. Well, so substack is basically just like a fancy word for a newsletter. It's like a program where people can have stuff behind a paywall. So, like, they might have a free newsletter they send out, but you pay to get their podcast or that sort of thing.

[Chelsea Handler (Ad Voice)]

It's.

[Chelsea Handler]

I mean, it's so you can put.

[Katherine]

A podcast on there that's not available anywhere else.

[Chelsea Handler]

Correct. Correct. Yeah. And so you can sign up for, like, updates. It's sort of like a new cool version of a newsletter that seems salesy. But.

[Katherine]

But why is there a platform for that?

[Chelsea Handler]

I don't know.

[Katherine]

Okay. Okay. I don't understand anything. I'm losing my grip on reality.

[Chelsea Handler]

That's okay. You know, we're just here to help you out with technology. I have an update from an episode that was a long time ago. So she wrote in. This is Elisa. She wrote in on our Heather Gay episode. So this is a while ago. She says, hey there. I was reminded today that I was on an episode in May 2023 and wanted to give you an update. My question was, how do I have casual sex when I can't make the first move? I shared that I was taking myself out on dates, sitting at the bar with a glass of wine and reading my book. I love happy hour and I love my own company. Well, I got asked out by a bartender, lol. He's a massage therapist that works a couple shifts a week at the bar because he likes the social aspect of that work. We dated for a year and ended up breaking up because I wanted to know where things were going and he wasn't ready to think about a future with me. A year passed and I accepted a job offer in another province of Canada. Big move to prepare for. While I was packing, my bartender declared his regrets and love for me, while cautious, I chose to give him a second chance. And we're currently in a committed long distance relationship. I love him very much and he is, as he says, accepting the suffering of the consequences of his choices. As he should. We'll figure out how we can be together after I finish a contract of two years. Will I last that long? I don't know. 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. You are my community. Much love, Alisa.

[Katherine]

What was the advice? This is like a journal entry.

[Chelsea Handler]

I mean what I know, but. Well, hey, 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.

[Katherine]

Did I tell her to go after it? To go get this guy? Did I tell her to have casual sex?

[Chelsea Handler]

I think we told her to like, like make the first move more. But then he did.

[Katherine]

Oh, okay, okay, okay. So another. Okay great. Well this is very anticlimactic, Katherine. Very anticlimactic.

[Chelsea Handler]

Elisa, let us know what happens in two years. We'll talk to you in another stream.

[Katherine]

And be specific about what the actual advice was. I don't remember what I fucking said to her. That was 2023.

[Chelsea Handler]

2023, aren't we?

[Brad Dickert]

Because I think the advice was about dating yourself. I think that's what you told her to do.

[Chelsea Handler (Ad Voice)]

Hold on. Straight man chiming in.

[Katherine]

Brad on that.

[Brad Dickert]

Hold on.

[Katherine]

Brad is on the scene.

[Chelsea Handler (Ad Voice)]

Do you remember this one?

Bran?

[Katherine]

Catherine is having a. Cathera. Cathera, that's your name now. Cathera. Kathra is having an inter office and inner office affair with her husband Brad who is our sound engineer. And that's his voice that you're hearing. Thank you Brad for remembering. Yes, that sounds like it tracks Brad. That I told her to date herself.

[Chelsea Handler]

We're at a studio where we've been coming for the last several weeks and I gave him a canoodle here in the office and I was like wait, did the other people here know that we're married or do they think we just carpool? We're married in case you guys did not know. Okay, so I have another follow up. This is from a more recent episode with Atsuko. This was about a gal who, her sister in law was like icing her out. There was like A B day party mishap where she didn't get invited to the niece's birthday party sort of thing. So she says, hi, Chelsea.

[Katherine]

I remember this.

[Chelsea Handler]

Yeah, yeah. Since we last spoke, I took your advice and had a conversation with my sister in law about what it was that had led her to cutting me off. A fact I should have mentioned from the start is that she is on the orange team, if you know what I mean. Oh, that took me a second. On the orange team, if you know what I mean. So the thought of having the conversation was extra daunting knowing I would probably not be met where I was at. It turns out the reason she cut me off was because I didn't wait until I saw her in person to discuss the birthday issue, causing my sister in law to get defensive of her daughter. I still can't believe this is the reason for the cutoff. Wow. I ended the conversation amicably by saying I love her and her daughter and only want to be in their lives. I've seen her at events since this conversation and things have been awkward, to say the least. I feel I've done all that I can and I certainly appreciate the advice to confront the issue head on. Despite the weird ending to the story. If this was any other relationship, I would have been done with it all. But as Chelsea said, we're family, so hoping things will someday improve. But for now, I think we're at a standstill. Thank you for everything.

[Chelsea Handler (Ad Voice)]

Stay.

[Katherine]

Yeah, well, now you have to employ Mel Robbins. Let them.

[Chelsea Handler (Ad Voice)]

Yes.

[Katherine]

Let her do her thing and let you do your thing. And it's not your problem. You stepped up to the plate, you did what you're supposed to do. There's nothing else you can do.

[Chelsea Handler (Ad Voice)]

Right?

[Chelsea Handler]

And like, if that's her reasoning for being upset with you, it's so stupid.

[Katherine]

Yeah. When you're dealing with people like that are holding onto very small, petty things, there is no. It's like. It is like dealing with the terrorist on the other end of the spectrum.

[Chelsea Handler]

Yes, yes. And you can only, you know, like Chelsea said, you can only be responsible for how you're showing up. Like show up with light and love and, you know, if she wants to be grumpy, let her be grumpy and that's fine.

[Katherine]

Exactly. Exactly. I concur, Catherine. I concur, Catherine. I concur.

[Chelsea Handler]

Excellent.

[Chelsea Handler (Ad Voice)]

You know, it's not fun waking up at 2am drenched in sweat. Been there. That's why I started using pod 5 from 8 sleep. And let me tell you, it is a Game changer. It's designed with women's help in mind, especially for those of us dealing with hot flashes. Pod 5 is this genius smart mattress cover that fits over any bed and pulls your body before a hot flash can mess with your sleep. And when I need an extra relief, I just tap the bed or use the app to activate hot flash mode. 30 minutes of instant cooling. It's like having a personal climate concierge. It's clinically proven to reduce hot flashes by over 50% and I genuinely sleep deeper and wake up feeling way more refreshed. I love that it's a non medical solution, but it's backed by real data and it feels totally natural. Anyone who listens to this podcast knows that I would like to sleep in a refrigerator and now I can. And if you sleep with a partner, Pod 5 cools each side of the bed independently. So no more kicking someone out for being a human furnace. You both get your perfect temperature from 55 degrees to 110 degrees. So go to 8sleep.com Chelsea use code Chelsea and get $350 off. You can try it risk free for 30 days. Trust me, better sleep starts here since.

I want the absolute best for my chow chow Doug I am making the switch to Ollie. Your dog's well being starts with their food and that's why Ollie delivers fresh human grade food that your dog will love. So head to ollie.com Chelsea and use code Chelsea to get 60% off your welcome kit when you subscribe today. Plus they offer a happiness guarantee on the first box so if you're not completely satisfied, you'll get your money back. That's Ollie O l l I e.com chelsea and enter code Chelsea to get 60% off your first box.

[Katherine]

From nursing and healthcare to business and.

[Chelsea Handler (Ad Voice)]

IT, Rasmussen has a range of programs.

[Katherine]

To fit your goals and passion no.

[Chelsea Handler (Ad Voice)]

Matter what your day to day looks like.

[Katherine]

Rasmussen's programs allow you to balance school.

[Chelsea Handler (Ad Voice)]

With life while you pursue your degree.

[Katherine]

So if you're ready to pursue your.

[Chelsea Handler (Ad Voice)]

Education goals, Rasmussen is ready to help.

[Katherine]

You take that next step.

[Chelsea Handler (Ad Voice)]

Head on over to Rasmussen.

[Katherine]

Edu and check out the opportunities waiting.

[Chelsea Handler (Ad Voice)]

Your future is a bright one.

[Katherine]

Rasmussen University can help you get there.

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[Chelsea Handler]

We just have a couple quickies today. So our first question comes from Mag.

[Katherine]

Maga. Great.

[Chelsea Handler]

She's on the orange team too.

[Katherine]

There's another Maga now. Make America Gavin again for Gavin Newsom.

[Chelsea Handler]

How do you feel about Gavin Newsom?

[Katherine]

I'm into it big time. Yeah? Yeah. You have to fight fire with fire. All these fucking idiots tiptoeing around, going, what? Crying and doing. Now he's doing something. And JB Pritzker. Is that his name?

[Chelsea Handler (Ad Voice)]

JB Pritzker.

[Katherine]

The governor of Illinois and Westmore. All these guys need to fucking do this. Yeah.

[Chelsea Handler]

Pritzker's been like, Donald Trump's been fighting back real hard.

[Katherine]

They need to really go after him.

[Chelsea Handler]

Yeah.

[Katherine]

So it's nice to see somebody fighting the fight.

[Chelsea Handler]

I agree. I think like the last few years, especially journalists and these, it's like everyone's being so polite and, like, respectful and like disagreeing, but in this really respectful way. And it's like you just can't.

[Chelsea Handler (Ad Voice)]

Oh, I know.

[Katherine]

You can't respect somebody who behaves this way and treats people in this way. It's disgusting.

[Chelsea Handler]

Right, Right. Well, Mag says, hey, Chelsea, as a 20something who's just starting to dive into the dating pool, I wanted to know if you have any advice on dating multiple men at once. Do it, she says. Is this a bitch move?

[Chelsea Handler (Ad Voice)]

No.

[Chelsea Handler]

If not, why do I feel bad about it? Meg.

[Katherine]

Yeah.

[Chelsea Handler (Ad Voice)]

No.

[Katherine]

Date people definitely do it. Absolutely.

[Chelsea Handler]

I was dating multiple people when I met Brad.

[Katherine]

Yeah, exactly. And what's wrong with dating multiple people?

[Chelsea Handler]

As long as everybody knows you're in the clear. Yeah, like we're not. I'm not exclusive. Not interested in being exclusive right now. And then if one grows on you like Brad did, then, you know.

[Chelsea Handler (Ad Voice)]

Exactly.

[Katherine]

Then you can eliminate the other gentleman callers. But absolutely do not. Like, there's nothing wrong with that.

[Chelsea Handler]

Also, like, who's got time to date one person at a time anymore? No, Keep it coming. Keep it coming.

[Katherine]

Exactly. Fresh meat every hour on the hour.

[Chelsea Handler]

And that way you don't feel like, okay, I just sunk two months into this guy and he ghosted me or whatever. You know, you got got people on the back burner. Our next question comes from lc. So I know you ditched your Tesla. So this is about ditching her Tesla? Dear Chelsea, as a fellow Tesla owner, I'm feeling deeply conflicted these days. Not because my car is judging me, but because my subconscious won't shut up about it. Given the current political climate and the ongoing Elon Trump saga, should I ditch my Tesla? Or are we just supposed to drive around pretend pretending it's an ultra fast self driving moral dilemma? Would love to hear your take, Elsie.

[Katherine]

I'm all for ditching the Tesla.

[Chelsea Handler]

Yeah, cause you ditched yours.

[Katherine]

Right? I ditched mine. My sister's waiting for her lease to be up, so she's not ditching hers. And I have judgment towards that. I feel like you have to stand on principles. Like, I'm sorry? Like you have to have principles and you have to follow through with them. And this. He doesn't deserve your money.

[Chelsea Handler]

No, agreed. And I mean, I do think for some people who maybe haven't given those back, they have that sticker. This is like the anti truck.

[Katherine]

First of all, the truck, the fiber truck. Yeah, I thought those all got recalled. Why do I keep seeing them?

[Chelsea Handler]

That's what I thought too. I mean, there was some part at least that got recalled on all of them. Brad will know the whole part.

[Katherine]

Yeah, well.

[Chelsea Handler (Ad Voice)]

Brad?

[Katherine]

Brad, where are you?

[Chelsea Handler]

You need a straight man.

[Brad Dickert]

You're talking about the cybertruck.

[Chelsea Handler]

Yeah, I think they got recalled.

[Brad Dickert]

Well, I think they just have an excess of inventory. I think they just have like 100,000 vehicles that they can't sell. So they're just sitting in parking lots everywhere.

[Chelsea Handler]

Yeah, but wasn't there like some stuff.

[Chelsea Handler (Ad Voice)]

No, but there was an issue where.

[Katherine]

They had to recall them.

[Brad Dickert]

Oh, I'm sure there's tons of recalls.

[Chelsea Handler]

Why do we know about this and you don't? You're a car guy.

[Brad Dickert]

Well, because it's a Tesla and I don't really care.

[Katherine]

Way to misrepresent. Way to misrepresent yourself and this podcast, Brad.

[Chelsea Handler]

What a disappointment. All right, goodbye, Brad.

[Brad Dickert]

I tried. Sorry.

[Chelsea Handler]

Well, on that note, we can go ahead and wrap up.

[Katherine]

Okay, well, don't buy a Tesla and if you have one, return it. Goodbye. I just announced all my tour dates.

[Chelsea Handler (Ad Voice)]

They just went on sale.

[Katherine]

It's called the High and Mighty Tour. I will be starting in February of next year so I will be touring from February through June. So go get your tickets now. If you want good seats and you want to come see me perform, I will be on the High and Mighty Tour.

[Chelsea Handler]

Do you want advice from Chelsea? Write into dearchelseapodcastmail.com Find full video episodes of Dear Chelsea on YouTube by searching earechelseapod. Dear Chelsea is edited and engineered by Brad Dickert Executive Producer Kathryn Lawrence. And be sure to check out our merch@chelsea handler.com.

[Chelsea Handler (Ad Voice)]

You know what's not fun? Waking up at 2am Drenched in sweat. Been there. That's why I started using pod 5 from 8 sleep and let me tell you, it is a game changer. It's designed with women's help in mind, especially for those of us dealing with hot flashes. Pod 5 is this genius smart mattress cover that fits over any bed and pulls your body before a hot flash can mess with your sleep. And when I need an extra relief I just tap the bed or use the app to activate hot flash mode. 30 minutes of instant cooling. It's like having a personal climate concierge. It's clinically proven to reduce hot flashes by over 50% and I genuinely sleep deeper and wake up feeling way more refreshed. I love that it's a non medical solution, but it's backed by real data and it feels totally natural. Anyone who listens to this podcast knows that I would like to sleep in a refrigerator and now I can. And if you sleep with a partner, Pod 5 cools each side of the bed independently. So no more kicking someone out for being a human furnace. You both get your perfect temperature from 55 degrees to 110 degrees. So go to 8sleep.com Chelsea use code Chelsea and get $350 off. You can try it risk free for 30 days. Trust me, better sleep starts here.

Dogs aren't just pets. We know this. Doug is one of the most important, if not the most important member of my family and certain the only man I want in my bed at the moment. Since I want the absolute best for my chow Chow Doug, I am making the switch to Ollie. They offer fresh protein packed meals made with real human grade ingredients. A win for Doug's health. And they offer five tasty recipes all slow cooked for top nutrition. A win for his happiness. Your dog's well being starts with their food and that's why Ollie delivers fresh human grade food that your dog will love. So head to ollie.com Chelsea tell them all about your dog and use Code Chelsea to get 60% off your welcome kit when you subscribe today. Plus, they offer a happiness guarantee on the first box, so if you're not completely satisfied, you'll get your money back. That's Ollie O L L I e.com Chelsea and enter code Chelsea to get 60% off your first box.

[Brad Dickert]

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[Chelsea Handler]

This is an iHeart podcast.