Dear Chelsea - Minisode: A Total Babe with Chelsea + Catherine

Episode Date: May 22, 2026

Chelsea and Catherine hear from a season 1-favorite caller, rein in a meddling mom, and cheer a fast followup.  * Need some advice from Chelsea? Email us at [e-mail] * Executive Producer Catherine Law Edited & Engineered by Brad Dickert * * * The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opinions of iHeartMedia or its employees.  This Podcast should not be used as medical advice, mental health advice, mental health counseling or therapy, or as imparting any health care recommendations at all.  Individuals are advised to seek independent medical, counseling advice and/or therapy from a competent health care professional with respect to any medical condition, mental health issues, health inquiry or matter, including matters discussed on this Podcast. Guests and listeners should not rely on matters discussed in the Podcast and shall not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.  See omnystudio.com/listener for privacy information.

This is an IHeart podcast. Guaranteed Human. Get rewarded just for shopping with Simon Plus. Don't miss Memorial Day sales at Simon Premium Outlets and Mills. You can get points at scores of stores, access to exclusive offers and exciting surprises. You've got an extra day off, so make it pay off, with the best deals from brands you love all in one place.

It's a summer kickoff thing. Join today at Simonplus.com. Rewards program terms apply. See simonplus.com for details. Hey guys, it's us. The Jonas Brothers. I'm Joe. I'm Kevin.

And I'm Nick. And guess what? We created our own podcast called, Hey Jonas. We invented a podcast? Well, we didn't invent it. We just contributed to us. We're the first people to do podcasts. We get to ask other people questions because we're sick and tired of being asked questions.

Well, sick and tired is a strong way to put it. But, you know, tired and sick. Listen to Hey Jonas on the Iheart radio app, Apple Podcasts, or wherever you get your podcast. Just listen. We don't care where you hear it. Another podcast from some SNL, late-night comedy guy, not quite. Unhumor me with Robert Smigel and Friends, me and hilarious guests from Jim Gaffigan to Bob Odenkirk, to David Letterman, help make you funnier. This week, my guest, SNL's Mikey Day and head writer Streeter Seidel, help an a cappella band with their between songs banter.

There's the worst singer in the group. First? Yeah. Me. Is there anything to the idea that because you're from Harvard, you only got in because your parents made a huge donation. The yard birds, right? That's the name. The Harvard Yard. But they're open. Do you have a name suggestion? We're open. Since you guys are middle-aged, one erection.

Listen to humor me with Robert Smygel and Friends on the I-Heart Radio app, Apple Podcasts, or wherever you get your. podcast. Huber me. I need some jokes to make me seem funny. Winning on Clay is an art. The rallies are relentless. And at the French Open, only the toughest survive.

I'd know. I competed there for decades. Join me, Renee Stubbs, on the Renee Stubbs' tennis podcast for no-nonsense breakdowns of the biggest matches, the toughest players, and the moments that define Roland Garris. She's an outsider to win the French win. And she likes Clay. Listen, Lina Rubakina is arguably the best player in the world.

world right now and I actually can win on any surface. Listen to the Renee Stubbs tennis podcast on the Iheart Radio app, Apple Podcasts or wherever you get your podcasts. Presented by Capital One, founding partner of IHeart Women's Sports. Okay, guys, here are my dates for the High and Mighty tour in May. The 30th of May I will be in Vegas at my residency. In June, I will be in Saratoga Springs, New York, Portchester, New York. I'm coming to Boston at the Wang Theater. I'll be in Portland, Oregon, Seattle, and then Hyannis, Massachusetts, and then two shows in Nantucket. In August, you can find me in Red Bank, New Jersey, Montclair, New Jersey, and Calgary. That's Canada.

And September, I will be in Santa Barbara, San Diego, New York City, Philly, and New Haven, Connecticut. October is Atlanta, Baltimore, Saginaw, Michigan, Pittsburgh, Toronto, Boise, Idaho, and Spokham. And then in November, I'll be in San Francisco. I'm coming to Salt Lake City, Austin, Houston, Dallas, babies. I'll be there. And then in December, I am closing out my tour in Denver and Vancouver. So get your tickets at Chelseahandler.com for the high and mighty tour. Chelsea, how are you?

Hi, I'm Chelsea. What's your name? My name's Catherine. It's nice to meet you, Catherine. It's a nice to meet you. It's a beautiful day here in sunny Los Angeles. It absolutely is. I'm safe in my house, my beautiful house.

house. You know what? It feels like you actually finally live here. I've had people. I've had people staying here. I had two my, two of my openings that come on the road with me, Yamanika and Megan Galey, they were staying here all week, so they broke in my guest room. Yamenica broke in my guest room for sure. Oh, broke it in. Not broke into it. She broke it in. And that's a separate issue. But the house is starting to feel like a home. I had a dinner party the other night. I had like six friends over. I'm going to do it again tomorrow night. I'm like, slow. Slowly. And the house is beautiful and I'm loving it and I'm grateful that I have a gorgeous house to live in. It's beautiful. It's like finally all put together. And like the nice little touches are coming

together. We've got our candle. Candle is going. I have a whole drug drawer. It's like everything is where I need to be. Party favors. Thank you. Incredible. I have an exciting update from a caller who took your advice and emailed me immediately after the call, like within 24 hours. She had taken this advice. So this was Simone, who was on our Kevin Kane episode. She had called in because she was like doing tarot, but, um, oh, yeah, yeah, wasn't charging for it and then was like worried, you know, wondering. I'm getting a tarot card reading today, by the way. Oh, my gosh. That's funny that you say that. How fun. Any particular reason? No, they just saw someone who said, can we give you a tarot card reading? I said, sure. I mean, how's that going to go? Why not? They already know who I am.

I don't know what doesn't even work anymore. That is like, I know everyone loves like Tyler Henry, but I'm like, it is so interesting to have like made your career like the most Googlerable people on the planet. I like that. That's going to be my complaint when people say, are there any downsides to being famous? I'm going to be like, yeah, you can't get her straight up fucking psychic reading or a tarot card reading. You've got to go to like Peru or something. But so Simone sent me her email that she sent out to all of her clients. And so I thought this was perfect.

Her subject line was, I've had a blast y'all, but something's got to change. Since the onset of my career almost nine years ago, I've been giving. out free readings, like an absolute shit ton of free readings. I want to talk to you today about why I did that and share a big announcement. I've done hundreds of free readings while secretly worrying about how I'm going to pay my bills. I still felt that my work might not be worth anything. But demand has been growing and after a swift kick in the butt from a long-time heroine of mine, I decided to transition to paid readings only. This is a big step for me and something wonderful to celebrate. For those of you reading this email now, you have a special price

that is only yours, lower than the public prices. This is my thank you for support. my business, use code, thank you Chelsea at checkout. Oh, yeah. That's so cute. I know. She said, I would love to help you manifest the reality you've been dreaming of, navigate a transition, or discover yourself more deeply by viewing your life through a broader vision. I want to express my sincere gratitude to those who have supported me along this journey. To those who have already purchased readings, thanks for teaching me the monetary value of my work. To those who received free readings, thank you for holding space for me as I worked through insecurities regarding my professional worth. I'm officially leaving those hesitations behind today. And even if you never

purchase from me, I want you to know just how deeply I appreciate every single one of you. But Simone's graduating. She's growing the fuck up. Tadda, thank you from the bottom of my little heart for being part of this growth and for your continued support. Best regards, Simone. I'm like, that is a perfect email. Like, I have a marketing background and that is a perfect email. Yeah. So do we need to remind people what that was about? Because that girl, she was giving out free tarot card readings. If you could introduce from the email. And she wanted to go professional, but she wasn't sure how to do that and how to tell people she's going to start charging and everything. And we said to write an email.

She said to write an email. Yeah. She was a great email. Great. I love it. That's so cute. So, yeah. So that was perfect. I was really, really happy. She did that. I know. And she, like, immediately did this. I was so proud for her. So that's so great. Get rewarded just for shopping with Simon Plus. Don't miss Memorial Day sales at Simon Premium Outlets and Mills. You can get points at scores of stores, access to exclusive offers, and exciting surprises. You've got an extra day off, so make it pay off, with the best deals from brands you love all in one place.

It's a summer kickoff thing. Join today at Simonplus.com. Rewards program Terms Apply. See Simonplus.com for details. The newest tracks. Let's go. New music. And the next big thing.

Always on the new music first. Your first place to hear it all. I'm going to like it, love I want to play it twice. Playing now. I Heart New Music. Your digital station for brand new drops, fresh vines, and tomorrow's bangers.

Powered by North by Northeast Music Festival, taking place June 10th to 14th across Toronto. Iheart new music. Stream now. Online on your smart speaker and preset on the free IHart. Hey, it's us to Jonas Brothers, and guess what?

We have some big news. What's the news, huge news? We created our own podcast called, Hey Jonas. We invented a podcast? Well, we didn't invent it. We just contributed to it.

We're the first people to do podcasts. Pretty, yeah, pretty wide range of podcasts throughout there. But this one's extra special. So how did we actually come up with a name, Hey Jonas, guys? I honestly don't remember. I think it was on a call about what we should call it. Well, we were thinking I'm originally calling it one of the early names of our band. Before Jonas Brothers was...

This is how you guys remember it going down. Yes. I have a very different memory of this. We were talking about a thing, a bit for the podcast, where people could call in and say, hey, Jonas. And then I wrote down on my little notepad, Hey Jonas, and offered it up as a potential title for the podcast. But thanks for remembering that, guys.

Listen to Hey Jonas on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Just listen. We don't care where you hear it. Another podcast from some SNL late-night comedy guide, not quite. Unhumor me with Robert Smigel and Friends, me and hilarious guests from Jim Gaffigan to Bob Odenkirk to David Letterman help make you funnier.

This week, my guest, SNL's Mikey Day and head writer Streeter Seidel, help an a cappella band with their between songs banter. There's the worst singer in the group. The worst? Yeah. Me. Is there anything to the idea that because you're from Harvard, you only got in because your parents made a huge donation.

The group. The yarn herds, right? That's the name. The Harvard Yard. They're open. Do you have a name suggestion? We're open. Since you guys are middle aged, one erection.

Listen to humor me with Robert Smigel and Friends on the I Heart Radio app, Apple Podcasts, or wherever you get your podcast. Humor me. I need some jokes to make me seem funny. And I have another update that's from a caller, not someone who called him, but I just thought this was sweet. Dear Chelsea, I'm not writing with a specific. question, but to thank you for all the thoughtful advice you've given others over the years since starting your podcast. I've been listening since day one. I know some people might ask themselves, what would Jesus do? But I'm more of a WWCS kind of guy. When one of life's stumbling blocks crosses my path,

I stop and think, what would Chelsea say? Most recently, I've been feeling stuck in my work life. My apartment lease was already month to month and I'm a single gay guy with no children. So I asked myself, WWCS. Then I refreshed my resume, learned how to harness the evil of chat GPT to assist me with writing cover letters and have been applying to jobs in cities across the country that I've always enjoyed visiting. No interviews yet, but I wanted to let you know that even without having to write you and ask, I knew what you'd tell me to do. And that was all I needed to jumpstart my initiative. Thanks for all the sage advice and laughs along the way, Anthony. What did he do? He was like, you know what? I need a big life change and started sending out his resume to other

cities and other places. And he's like, I don't have a mortgage that's going to tie me down. I don't have kids. Time me down. Yeah. Everybody needs to keep it moving. Everyone just keep it moving. If you are in a point in your life where you're dissatisfied or you don't think you're realizing your full actuality or like dreams, then move. Make a big change. Make a big change. Yeah.

Life rewards you, I think, when you make big changes. I think so too. Yeah. But also, write in because we love having people right in. Yes, I love to get advice. I love it. We always need new questions. Okay.

Chelsea, are you ready to talk to a familiar face from maybe six years ago? So Shane is writing in. Is this Shane Gillis from the roast? Absolutely. It absolutely is. Weren't you excited to see him again? Yamanika kept calling him Sean. Like that's incredible.

I mean, I never heard him before. So that's racist Yamanika. All the Shains and Shots look alike. Okay. So Shane is from season one. This is the guy who you two took a 30-day weed break with. Or you took 30-day we break with him. Yes.

Yes. We love Shane. Hey. Oh my God. Hello. What exciting is this? We need our headphones. Oh, we do need our headphones.

Oh, my God. I know, Shane. I follow him on Instagram. Prison is not a joke. That's me. Hi, baby. How are you? How are you?

Thank you. So do you. Yeah, thank you. He looks so handsome. I love it. Well, Shane has some messy stuff that we have to dig through. Okay. So I'll go through the list and this is all very succinct.

Hi, Chelsea, it's Shane, your 30-day weed break buddy from season one. Remember me? When we finished that break, I had just unexpectedly come out to my family as trans. So while we were moderating weed, I was quietly detonating and rebuilding my entire identity. Very chill timing. Since then, life's been eventful. At the start of 2025, I had a three-week breakdown that landed me on Luxa Pro. During that time, I did a short weed break because smoking was making my anxiety worse, but I ultimately went back to smoking every day. No vapes, though. If I have a little bit of one, I'll hit it every seven to 12 minutes like I'm checking notifications. Toward the end of the year, I quit my job of almost seven years, got evicted, not my fault, just capitalism, and lost

a friend to liver failure. On the positive side, I recently started a new job, which feels like a real reset. Nothing motivates personal growth, quite like losing everything all at once. Also, because I clearly enjoy a side quest, I've developed a nicotine pouch habit. In my state, they're not even flavored, just raw, unseasoned nicotine. It's basically the lacroix of bad decisions. So my questions for you are, do we need another 30-day reset? Do I include nicotine this time? And where's your personal weed line these days? Love Shane.

Hi. Oh, yes. Hi. Okay. My personal weed line I gave up on, honestly. There's too many idiots in the weed industry that I went through down the road like three different times with three different groups of men. And I was like, I don't want to work with men.

I just can't deal with it. I came out with my Owlsbrough, Chelsea Lemonade instead because that was a women-led company. and they came to me and they nailed it the first time. Like our first taste test, I found three flavors that I loved. And I was like, this is, I've been down that road with men so many times. So my owls brewed vodka lemonade was replaced my weed thing. But I still, you know, I mean, I smoke and use drugs all the time. Okay.

Can I ask a clarifying question? Shane, did you mean a line of weed that's Chelsea branded or your personal line with how much you smoke weed? No, she was the first time we talked to you were saying that you were going to have your own line of weed. Right, right, right. I read it the other way. Yeah.

So, well, I guess that's why it's called Dear Chelsea, Catherine. So, yeah, you should do a 30-day reset. You have an addictive personality. I know. It's okay. I do too. I do that. I do too.

So I have to like, sometimes if I'm just doing too much of one thing, I just stop and then pivot to something else so that I don't ever have to have give away. I don't want to ever have to give anything up. You know what I mean? But 30-day reset is great because you don't have to give it up. You just have to stop for 30 days. and that'll tamp down your desire. Yeah, I do want to give up a nicotine for sure.

Yeah, that's a bad habit. That's an achy habit. Yeah. I need you guys to publicly shame me so I can put it. Okay, do you want me to pretend to quit something for 30 days and do it with you? Yes. What could I quit for 30 days? What's my favorite drug right now?

LSD, but that's not fair to the world because that's good for me to be on. Hold on. Let me think of something else. Ketamine? Ketamine. I hate ketamine. I try to. I tried it on that boat ship.

And that should be easy to quit for 30 days. Yeah. Okay, fine. I won't do catabine for 30 days. We're in solidarity. Do you feel the love chain? I do. How's your life going?

Right now it's pretty good. I'm starting to put my life back together. I got a new apartment and new job. Oh, nice. Yeah. So I'm just chilling. How's a new job going? I've only been here for like two months, so I don't really fully know everything yet.

But I feel like I can do most things by myself at this point. It's shipping and receiving for a kind of. in Berkeley. So easy stuff. And how are you like, how did everything shake out with your family when you came out and like did all of that? They overall were cool with it, but they still like fuck up pronouns in my name and I'm constantly correcting my parents on that. But they're old, so I'll let them pass. Yeah, that's okay. That's okay. Just keep reminding them. They'll get it. Yeah. Yeah. Sooner later. Well, Shane, I love you. I love our relationship. I love that you are calling back after six years and I love seeing you on Instagram. Yeah. This is my longest.

relationship right here. Me too. Me too. Okay, my black brother? Me too. Well, thank you so much for having me back. You're right. You're welcome anytime, buddy. Bye. Okay. Bye. Get rewarded just for shopping with Simon Plus. Don't miss Memorial Day sales at Simon Premium Outlets and Mills. You can get points at scores of stores, access to exclusive offers and exciting surprises. You've got an extra day off, so make it pay off. with the best deals from brands you love all in one place.

It's a summer kickoff thing. Join today at Simonplus.com. Rewards program Terms Apply. See Simonplus.com for details. I'm Cynthia Lois. And I'm Josie Dye. And we're done pretending we have it all figured out. Each week we laugh, cry, and talk our way through life's messiest moments.

The things you think about but would never say out loud. The questions you are always too shy to ask. Relationships, regrets, awkward moments, and the stuff no one warns you about. It's honest, it's funny, and sometimes it gets a little uncomfortable. But that's kind of the point. This is Cynthia and Josie's unmentionables. Listen on the free IHeart Radio app or wherever you get your podcasts. Hey, it's us to Jonas Brothers, and guess what?

We have some big news. What's the news, name? Huge news. We created our own podcast called, Hey Jonas. We invented a podcast? Well, we didn't invent it. We just contributed to it. We're the first people to do podcasts.

Pretty, yeah, pretty wide range of podcasts throughout there. but this one's extra special. So how do we actually come up with a name Hey Jonas, guys? I honestly don't remember. I think it was on a call about what we should call it. We were thinking I'm originally calling it one of the early names of our band

before Jonas Brothers. This is how you guys remember it going down? Yes. I have a very different memory of this. We were talking about a thing, a bit for the podcast, where people could call in and say, Hey Jonas.

And then I wrote down on my little notepad Hey Jonas and offered it up as a potential title for the podcast. But thanks for remembering that, guys. Listen to Hey Jonas on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Just listen. We don't care where you hear it. Another podcast from some SNL late night comedy guide, not quite. Unhumor me with Robert Smygel and friends. Me and hilarious guests from Jim Gaffigan to Bob Odenkirk to David Letterman,

help make you funnier. This week, my guest, SNL's Mikey Day and head writer Streeter SideEyeyeyeye help an a cappella band with their between songs banter. There's that worst singer in the group? The worst? Yeah. Me. Is there anything to the idea that because you're from Harvard,

you only got in because your parents made a huge donation. The yard birds, right? That's the name. The Harvard Yard. But they're open. Do you have a name suggestion? We're open. Since you guys are middle aged.

One erection. Listen to humor me with Robert Smygel and Friends On the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Humor me I need some jokes to make me seem funny. I love how they're using the wrong pronouns and he has like a full beard. Like just... Yeah, he was he transitioned from a woman, right?

Mm-hmm, mm-hmm. I mean, he's like a dude. First of all, he's a fucking a babe. He's a babe. He's a babe. Yeah. He's very hot. He's very hot.

If any of you are out there in the Bay Area looking for a cute trans guy to date, I mean, shame. Yeah. Yeah. That's nice. So cute. All right. I have a one drink question we can wrap up with.

We have a mom who might be overstepping a little bit, but I'll let you take this one. So Brenda says, hi, Chelsea. I know that you're now doing that matchmaking on Instagram and I love that so much for you. I'd love to be a matchmaker myself, but I'm not sure how to go about it. Enough about me. my daughter moved to Barcelona several years ago and she's an English teacher and I want so badly for her to have a great love and she hasn't experienced that yet in her life. I know what would make her feel like she was chosen. Not that you have to be chosen when you can do the choosing, but that's something that has not clicked for her yet. When I went to visit recently, I sat in a cafe and met a very nice man for her, but he ghosted and I don't think she likes the idea of me trying for her, but I can't help myself. She's so deserving of a loving and kind partner. If you get any people from Barcelona, She's a lovely girl who's soon to be 26 years old. Can you please add them to your Instagram, Brenda?

26 years old is like not old. A baby. She's going to be fine, mom. And you like, don't meddle like that. If she doesn't like that, don't do it. I know you can control yourself. You're her mother. Like, and yes, I'll look out.

There were a bunch of people from Barcelona, actually. But we were focusing on this country. So I'll talk to my social media team and have them focus on like geo target places. But I can't guarantee that we'll put her up because I'm being bombarded. I mean, it's just, it's too much to manage. And so I'm doing the, we're doing the best we can. I'm not doing it.

My social media team is doing it because it's so much. But also, respect your daughter's wishes. Your daughter will be fine. She's 26. She'll meet people. Don't worry. It happens. It's got to happen, like, of her own volition.

Organically, yeah. Yeah, or online or whatever. But yeah, I feel like, that's nice that that guy was very nice to her, but also like, of course he ghosted. You know, it's like, oh, my daughter's so sweet and lovely. Like, you know, it's just, you got to let her do it on her own, I think. Yeah, yeah.

All right, Brenda. Well, that's all for this week. Peace out. Peace out, guys. If you want advice from Chelsea, write into Dear Chelsea Podcast at gmail.com. Dear Chelsea is a production of IHeartMedia. Follow Chelsea on all socials at Chelsea Handler

and find Catherine on TikTok at Flashcadabra. Dear Chelsea is edited and engineered by Brandon Dickert, executive producer Catherine Law. Find full video episodes and minisodes now on Netflix and get tickets to see Chelsea Live at Chelseahandler.com. Get rewarded just for shopping with Simon Plus. Don't miss Memorial Day sales at Simon Premium Outlets and Mills. You can get points at scores of stores, access to exclusive offers and exciting surprises. You've got an extra day off, so make it pay off with the best deals from brands you love all in one place.

It's a summer kickoff thing. Join today at Simonplus.com. Rewards program, Terms Apply. See Simonplus.com for details. Hey, guys, it's us. The Jonas Brothers. I'm Joe. I'm Kevin.

And I'm Nick. And guess what? We created our own podcast called, Hey, Jonas. We invented a podcast? Well, we didn't invent it. We just contributed to it. We're the first people to do podcasts.

We get to ask other people questions because we're sick and tired of being asked questions. Well, sick and tired is a strong way to put it. But, you know, tired and sick. tired and sick. Listen to Hey Jonas on the Iheart radio app, Apple Podcasts, or wherever you get your podcast. Just listen. We don't care where you hear it.

Another podcast from some SNL, late night comedy guy, not quite. Unhumor me with Robert Smygel and friends. Me and hilarious guests from Jim Gaffigan to Bob Odenkirk to David Letterman help make you funnier. This week, my guest,

SNL's Mikey Day and head writer Streeter Seidel, help an acapella band with their between songs banter. There's that worst singer. In the group. The worst? Yeah. Me. Is there anything to the idea that because you're from Harvard,

you only got in because your parents made a huge donation. The group. The yard birds, right? That's the name. The Harvard yard, but they're open. Do you have a name suggestion? We're open. Since you guys are middle aged.

One erection. Listen to humor me with Robert Smigel and Friends on the I-Heart Radio app, Apple Podcasts, or wherever. you get your podcast. Cuba me. I need some jokes to make me seem funny. Winning on Clay is an art. The rallies are relentless.

And at the French Open, only the toughest survive. I'd know. I competed there for decades. Join me, Renee Stubbs, on the Renee Stubbs' tennis podcast for no-nonsense breakdowns of the biggest matches, the toughest players, and the moments that define Roland Garris. She's an outsider to win the French win. And she likes Clay.

Listen, Lennarabakina is, again. arguably the best player in the world right now and I actually can win on any surface. Listen to the Renee Stubbs tennis podcasts on the IHeart Radio app, Apple Podcasts or wherever you get your podcasts. Presented by Capital One, founding partner of IHeart Women's Sports. This is an IHeart podcast. Guaranteed Human.