Dear Chelsea - Minisode: Bad Parenting with Chelsea + Catherine

Episode Date: September 25, 2026

Chelsea and Catherine attempt to tackle some serious questions… and get a PSA on honeys and sweeties.   * 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 I-Heart podcast. Guaranteed Human. Okay, guys, here are my dates for the High and Mighty Tour. In September, I will be in New York City, Philly, and New Haven, Connecticut. October is Atlanta, Baltimore, Saginaw, Michigan, Pittsburgh, Toronto, Boise, Idaho, and Spokane. 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. Hi, Catherine. Hi, Chelsea. Hi. Are you ready for our minisode today? I am ready for our minisode.

Estuilista para Neuestra minisode. Very nice. Well, I have an update from Jeannie, who had called in in our Adam Scott episode, and her mom had, like, gone full MAGA, and she was wondering whether to unbreak up with her mom. And what did we tell her? We told her, yes.

Break up with her. No. No, we said, it's okay. Oh, she's mental illness, I said, right? Yes, yes, yes. Consider it to be a mental illness. So she, Jeannie says, hi there. I wanted to let you know that I followed Chelsea's advice to a T two days after we recorded

the podcast. My mom was eager to put the past behind us. She immediately shared stories of what's been going on with her as if nothing had happened. My piece has been restored, which is what I wanted. We don't talk her text as much as we used to, but I can live with that. I have no plans on buying a plane ticket to visit her and my stepfather because part of me still feels disgusted with both of them. I've tried to reframe my view of her as being ill as Chelsea advised, but it is hard.

Since the podcast aired, a couple of friends have reached out and shared that they struggled with their MAGA family as well, and your advice really helped them. All this is to say, people are incredibly complicated. We can all be good and bad, kind and callous, wise and naive. I may never be able to square the contradiction that is my mother, but at least I can continue to have her in my life. She is still teaching me lessons whether she intended to or not. There you go. That's a good outlook. Yeah.

Yeah. I think so too. Well, are we ready for Sydney? We have a theme of like some parents behaving badly in this episode. Okay. So Sydney says, Hi, Chelsea. My name is Sydney.

I'm a longtime listener and fan. Well, the time has come and I need some advice. To make a long story short, I went no contact with my absent dad about six months ago. I've been ignoring calls and texts, and honestly, it's been a relief not having him in my life on my terms. My sister is 11 years younger than I am, and she loves our dad because he actually was one to her. I know it bothers her that we don't get along, but I really try not to involve her in our shit. Nonetheless, my shitty dad, who lives in Florida, by the way, decided to disregard my boundaries and show up, unannounced, to my house in California because he knew I wouldn't answer the phone. Turns out my sister knew about his plan and didn't think to warn me.

She claimed she didn't want to get involved or choose sides, yet she told my dad what my work schedule was so that he could plan his trip for when I'm off. Do I have a right to be royally pissed with her? I'd love some insight. Have a great day, Sydney. Hi, Sydney. How are you? Good. How are you guys?

Good. You know, it's interesting hearing your letter, like, I think there's a difference. There's two different kind of people, possibly more. Okay. Some people are sentimentally attached to relationships with their family for very very. variety of reasons. I mean, it sounds like your sister had a more present dad, but also like I'm in a situation with my family where I'm not really speaking to my brother and his wife and that side of the family and their kids just because I just don't like some of their views and and I don't really

want to infect my brain with it in this time. And everyone kind of agrees, but no one would cut off. You know, they're like, they'll still interact and they just ignore that part of them. But I don't have any sentimentality about it. Like I'm not up at, night thinking about it. It's just easier for me not to have it. So I can relate to what you're saying a lot. And I also understand what you're saying about your sister. It's kind of like the letter you just read from someone else who didn't want to cut off their mom and their mom had become MAGA and like they were really, you know, kind of torn because they wanted their mother in their life. But every time they were, you know, they get into the political stuff. It was just ugly. So it's like I'm,

I have a very no frills attitude about it. I don't get emotionally attached to that kind of stuff for some reason or maybe I'm missing some sort of emotional DNA. But I definitely think that your sister needs to understand, have a better understanding of like what your boundaries are. You know, like, I don't think it's cool that she did that. She didn't do it to be malicious, but she needs to not, she needs to understand where you're coming from and why it's a boundary that's crossed. So have you had any conversations like that with her? Yeah. So she, she's 11 years younger than I am. So for her, college spring break she came out here and it was like right after i had done the no contact thing with him and she and i went to lunch by ourselves and we had a whole discussion about because she didn't know

a lot of my childhood because they don't talk about it and i never wanted to put that on her because she was a kid so i opened up to her and i told her a lot of really heavy things and she was like that's crazy okay and totally understood why i cut them off and why i did it want to have a relationship with them anymore. But then I found out that she knew that he was planning to come while we were having that discussion. And she didn't think to go like, hey, well, just heads up. He might be coming. Right. Have you talked to her about it again after? No. So it's been a little over a month. When I, it happened, she was working as a little camp counselor at a Jewish camp. So I didn't want to bother her while she was like fully immersed in her camp. And so I thought maybe she would reach out

because I wasn't ready to. And now it's been over a month and we just haven't spoken. And she's very avoidant. So unless I reach out, we're not going to. And I don't know if I am ready because I'm going to hurt her feelings. Well, it's not about hurting her feelings.

It's about setting up boundaries for yourself, which is going to be a lesson and modeling for her also. Yeah. Since she is 11 years younger, like, it's if you're like you're enabling that behavior by not saying anything. Do you know what I mean? Because if you don't say anything and then

she does it again, then you only have yourself to blame. Right. Yeah, I think you've got to go like full big sister mode on this and like handle this from your wisest self. And remember that like she's what, 20, what, 20, 21? Twin. Yeah. So like she's a baby.

The main thing she knows about social interaction is like high school stuff is like early college stuff. So I think this is something we really have to take her hand to be like, I'm sending a boundary with dad. That doesn't mean that you have to. But like I need you to respect my boundaries. And I think it's less about, like, hurting her feelings as just, like, really going big, like, wiser, older sister with her and just having a really serious discussion, but, like, telling her you love her. You understand why she, you know, maybe tried to help dad get to you, but, you know, that can't happen moving forward.

How was it with your dad when you he did come? It was rough, Chelsea. Let me tell you. He's a very, very narcissistic tendencies. So everything, there was no accountability ever. He was like, yeah, we can talk about all the things that you don't like about me. But anytime I would bring something up, it's someone else's fault. So she blamed my mom heavily on so many things, blamed medical issues, blamed the economy, blamed everything but himself.

Not the economy. My behavior is a result of the economy. Oh, the good old recession. You know, that got him and he couldn't parent anymore. Right. So, yeah. So it just, it was rough. And then he wouldn't leave too because I did let him in because my mom was like,

Miha, let him in. And I regret it because he wouldn't leave. And I had my baby. And I was like, dude, I got to put my baby for a nap. And he was like, no worries. I'll go to the garage and smoke some weed. You know, I'll get out of your hair. And I'm like, no, I need you to like leave, leave.

Yeah, yeah, yeah. Like you came uninvited. Yeah. Yeah. Yeah. Just have a gentle, loving conversation with your sister and just, you know, if she's avoidant, this is a good opportunity or a good learning. Like, you can show her how it's done.

Don't be avoidant because she's avoided. Yeah. No, I think I'm getting to the point where I'm ready. I just, I knew that if I had done a conversation sooner, I would have, I would have hurt her feelings. Totally, totally. I was too heated. No, I think you bring up a good point because I feel like we've talked a little bit about this on the show.

this is something I'm learning in my life, but just like when something makes you feel hot, when you're upset about something, like, just taking some time. And even if that time is like a month that you need to just like think about it and mull it over and like let the, you know, the hotness dissipate, I think that's the best decision. Yeah, because this is like 20 years of background shit with my dad. So it's, yeah, it's pent up. Yeah. It's pent up. And she knew about it. That's why it hurt. Yeah. And bottom line, your dad is the, one who broke the boundary. Like you're really angry with him and not with her.

So yeah, I think it just got to be like Chelsea said really gentle. Yeah. Yeah. Okay. Well, thank you guys. All right. Well, thanks for calling in and thanks for being so thoughtful. Okay.

Well, thank you guys. I appreciate your help. Okay. Take care. Do you ever think about a random pop culture moment? Like something that dominated the culture and then quietly disappeared? We do constantly. This is Bestie Listen.

Every week, we revisit the most niche corners of pop culture. culture. The stuff that shaped us, or better or worse. And ask, what was that? And more importantly, why do we love it? We celebrate it. We question it. And give it the level of analysis it absolutely did not ask for. Stream best you listen on Iheart Radio, crave, or wherever you get your podcasts. All right. Well, we'll wrap up with a shorty here. Jeffrey is writing in. Jeffrey says, I'm a guy in my mid-30s and I've always had a difficult relationship with my mom. A few times a month, I vent in the sixth sibling group chat and completely roast her. I call out all her flaws.

I don't hold back. It's not always nice, but I never lie. In a strange way, it feels therapeutic. Is the mom on the group chat? No, no, no, this is just siblings. So things have gotten even more complicated since my 82-year-old father passed away this past December. For added context, she's in her mid-50s and was the other woman when he left his wife and there are seven kids for her.

Oh. There's a lot of buried anger and unresolved trauma. So here's my question. Should I stop doing this? Am I being too mean or bitter? Am I holding on to something I should just let go of? Or is this a justified outlet for a longstanding pain? Thanks for your honesty. I know you'll set me straight, Jeffrey. I think airing your frustration and anger or, you know, however you want to frame it is good to do with a therapist or a professional. I think putting it in a thread and writing it down gives it more power somehow. than actually talking through it with someone who is not part of your family.

Like, I just think the bitching leads to bitching, begets more bitching, and then you just become, even if it's just a burst, it's just a negative thought pattern that you, and writing it down is just, it's like doubling down. So I understand your frustration, your anger, all of those things, but I don't think that's the right outlet for it. And it's kind of like, yeah, you don't, like, unless you have, It's kind of the perfect thing I think of texting as if you don't have anything nice to say, don't say it. And certainly don't put it in writing.

Also, everything that you're putting in writing is stored somewhere. So think of it that way. Like it's just not worth it in this day and age to be putting that kind of stuff down. And also just like for your own mental health, it does, you know, it does become a sort of circulating cesspool of like negativity when you're constantly thinking like what other nasty thing can I say. I think, yeah, I think this is a job for a therapist. Go talk to somebody about it. Like, vent it out.

And like maybe just, yeah, maybe not in the group chat. Yeah. All right. All right. Well, thanks, Jeffrey. Case closed. Yeah, case closed. See you next week.

Okay, bye. 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.

This is an IHeart podcast. Guaranteed human.