Minisode: Perspicacity Chelsea + Catherine

Summary

Dear Chelsea - Minisode: Perspicacity Chelsea + Catherine

Podcast: Dear Chelsea (iHeartPodcasts)
Air Date: September 5, 2025
Hosts: Chelsea Handler and Catherine Law
Featured Caller: Dwayne

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Overview

This minisode of Dear Chelsea dives into language, family complications, and self-awareness as Chelsea Handler and Catherine Law give their signature blend of witty, honest, and heartfelt advice. The episode opens with a lighthearted vocabulary intervention inspired by a listener request, then shifts to tackle difficult family dynamics—including aging parents in challenging relationships. The hosts finish by addressing how to nurture relationships with less-favored family members, all while providing their trademark humor and candor.

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Key Discussion Points & Insights

1. Parking Gate and Self-Deprecation (02:31–03:23)

• Chelsea and Catherine open with a comedic exchange about parking mishaps, emphasizing a forgiving attitude toward personal incompetence and daily frustrations.
• “Thank you for feeding my meter today for me, because I'm incompetent, and I can't park in a parking structure.” – Katherine Law (02:35)
• Chelsea shares she isn’t car-savvy either, keeping the tone light and relatable.

2. “Perspicacious” Vocabulary & Listener Segment (03:26–05:29)

• Listener Justine writes in, hilariously calling out Chelsea’s high-brow vocabulary and suggesting a vocab segment for fellow “plebeians.”
  • “You think Rob Lowe knows what perspicacious means? Vocab queen…” (Listener Justine, read by Chelsea, 03:36)
• Catherine explains “perspicacious” and other favorite big words:
  • "Perspicacious means very perceptive, so I'm just being a Cunt. ...because it's such a mellifluous word." – Katherine Law (04:38)
  • Definitions for perspicacious, perspicacity, chicanery, and a discussion about the joy of learning new words.
• The hosts agree to introduce a recurring vocabulary segment for audience enrichment.

3. Caller: Dwayne – Navigating an Aging Parent’s Toxic Relationship (05:34–16:47)

Dwayne’s Situation (05:43–08:06)

• Dwayne (47, gay, only child) shares about his mother’s long-term boyfriend Bob, whom he finds annoying, misogynistic, and dishonest.
• Dwayne’s mother, almost 81, stays with Bob largely due to loneliness, despite sleeping in separate bedrooms and his obvious flaws.
  • "She says his company is better than nothing." – Dwayne (07:07)
• With his mother’s upcoming hip surgery, Dwayne is looking for advice to protect her (emotionally and legally) and increase her happiness.

Chelsea & Catherine’s Advice (08:06–16:47)

• Exploring Senior Living/Retirement Communities:
  • Chelsea suggests options like Sun City or similar senior communities to combat loneliness and increase social interaction.
    • "Those are places that are designed to help you continue to have social interaction... not just with one person..." – Chelsea Handler (10:08)
  • Catherine underlines using the hip surgery as a potential chance for transition: “You could move in with her while she’s healing, and that could be her introduction into one of those places...” (10:35)
• Emotional Reality:
  • Acknowledges the difficulty in convincing an elderly parent to uproot their life, especially with deep ties to their hometown.
  • Stresses companionship and autonomy for seniors and the commonality of non-romantic relationships at this stage.
• Legal Protection:
  • Chelsea strongly recommends that Dwayne see an elder law attorney and estate planner to ensure Bob can't claim inheritance or property undeservedly.
    • "You got to see an elder law attorney, not just an estate planner..." – Chelsea Handler (13:10)
  • Catherine frames the legal discussion around the imminent surgery:
    • "This hip surgery is a perfect excuse to do all of this stuff. Get your ducks in a row..." – Katherine Law (13:19)
• Alternative Options:
  • Discussed the idea of Dwayne installing a tiny home for his mother on his property to keep her close and involved, as well as the flexibility and appeal of local senior communities.
  • Emphasizes on presenting all these choices kindly—not dictating, but supporting.
  • “Even if she moves into a place, you're still going to be there to help her with her hip after.” – Catherine Law (15:39)
• Reassurance to the Caller:
  • Chelsea and Catherine validate Dwayne’s protectiveness and urge him to continue being proactive and loving.

Affirmation from Caller (16:47)

• Dwayne expresses deep gratitude for their advice:
  • "I appreciate it so much... Not even just my question, all the advice that you guys give other people, I find so...pertaining to me a little bit." – Dwayne (16:48)

4. Listener Mail: Playing Favorites as an Aunt (21:16–23:36)

• Listener Ann confesses to having “favorites” among her nieces and nephews, particularly with her oldest sister’s kids, and worries about her bonds with others in the family.
  • “My sisters both have kids ... I feel a strong bond with three of her four. The fourth is just okay.” (Ann, read by Chelsea, 21:19)
• Catherine’s Guidance:
  • Direct and humorous: “You’ve already chosen your favorites…go and put in the time to the one that… has been neglected. She’ll appreciate that.” (22:22)
  • Encourages Ann to build a better relationship by making intentional, personalized gestures, and proactively spending time with the cousin who feels left out.
    • "One-on-one dates, gestures...trinkets of stuff you know she likes…" – Catherine Law (23:05)
• Chelsea’s Reassurance:
  • “You’re such a good auntie.” (23:33)

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Notable Quotes & Memorable Moments

• Chelsea on “Superior Dialect”:

  • “Maybe it can be a new mini-segment. Thanks in advance, Justine.” (04:28)

• Catherine on Big Words:

  • “I’m just being a Cunt by saying perspicacious. Because I love the way … cause it’s such a mellifluous word.” (04:38)

• Chelsea on Retirement Living:

  • “You're in a community of other people who are like you, and you don't just have this one person who's, like, living in your house.” (10:08)

• Catherine on Legal Protections:

  • “Get your ducks in a row that you’ve spoken to an elder law attorney, … you want to make sure that if anything happens to her that Bob doesn’t....” (13:19)

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Timestamps for Important Segments

| Time | Segment | |------------|---------------------------------------------------| | 02:31 | Hosts’ humorous parking story | | 03:26 | Listener Justine: Vocab segment request | | 04:38 | Catherine explains big words, new vocab segment | | 05:34 | Dwayne’s email: mom’s troubling relationship | | 08:06 | Dwayne joins live for further discussion | | 10:08 | Chelsea: Senior community/social options | | 13:10 | Elder law and estate planning advice | | 15:39 | Alternative housing and family solutions | | 16:47 | Caller gratitude wrap-up | | 21:16 | Ann’s letter: favoritism among nieces/nephews | | 22:22 | Catherine’s actionable advice for Ann | | 23:36 | Episode wind-down, show plugs |

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Episode Tone and Language

The episode is upbeat and comically blunt, blending snark, self-awareness, and genuine concern. Both Chelsea and Catherine keep the mood warm, supportive, and often self-deprecating, making space for vulnerability and laughter—while driving home practical, actionable advice for listeners.

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Summary Takeaways

• Vocabulary Expansion: The hosts will add a recurring segment defining Chelsea’s “SAT words.”
• Family & Aging Advice: When coping with elderly parents in problematic partnerships, combine compassion, practical support, and legal oversight—including serious estate and housing conversations.
• Auntie Guilt: It’s never too late to improve family bonds—intentionality and attention go a long way, even when you admit to having “favorites.”
• Signature Style: Listeners can expect both insight and irreverence, with real-life stories, humor, and a lot of heart.

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For advice or to hear more from Chelsea and Catherine, write in to [e-mail] or find full episodes on YouTube and at ChelseaHandler.com.

Transcript

[Chelsea Handler]

This is an I Heart podcast.

[Katherine Law]

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[Katherine Law]

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[Chelsea Handler]

Hello, Chelsea.

[Katherine Law]

Hello. How are you?

[Chelsea Handler]

I'm great.

[Katherine Law]

Thank you for feeding my meter today for me, because I'm incompetent, and I can't park in a parking structure.

[Chelsea Handler]

I mean, I am incompetent when it comes to knowing what cars are. So. I knew it was a silver car. There were a lot of silver cars. And I definitely had to, like, beep the key rings for it.

[Katherine Law]

First of. Okay. And I. Yesterday, you guys gave me, like, a. I want to say certification.

[Chelsea Handler]

Validation.

[Katherine Law]

Validation for my car. And I get down to the parking lot, pull out. I have everything but the fucking ticket, of course. And I'm a hot mess. You know, Everything's a hot mess with me. And I. So I'm like, fuck it. I pay $25 to record my own podcast. And then this morning, I get out of the car, and there's the validation ticket. I'm like, this is a mess. Everything I do is a mess.

[Chelsea Handler]

You know what? It's okay. We're gonna give you validation.

[Katherine Law]

I know. It's like somebody needs to just come and park my car every single day.

[Chelsea Handler]

Yeah. Well, I have a suggestion from a listener that I thought was kind of.

[Katherine Law]

Funny as it is for me, personally.

[Chelsea Handler]

Kind of.

[Katherine Law]

I love it.

[Chelsea Handler]

I am actually curious what you're gonna think about this. Oh, great. Justine says she wrote in, and her subject line of her email is, you think Rob Lowe knows what perspicacious means? Vocab queen, she said, dear Chelsea, I think my vocabulary is pretty respectable, particularly for an American at this point in time. Yet my workouts are routinely interrupted when I have to pause and Google the definition of some big word, one that you know damn well your guest does not know the meaning of. You think Rob Lowe knows what chicanery means? Perspicacious? Please.

[Katherine Law]

He's too beautiful.

[Chelsea Handler]

And so am I. I mean, you're a goddamn hero for our culture. You're educating the masses, but you're also interrupting my flow. So here's my pitch. Can you decode your superior dialect for the rest of us plebeians at the end of each episode so we can all become less stupid together? Maybe it can be a new mini segment. Thanks in advance, Justine.

[Katherine Law]

Yeah, That's a great idea.

[Chelsea Handler]

I know. I was like, I love that.

[Katherine Law]

I love that idea. Vocab words. We all need to build our vocab. Yeah. Yeah, for sure.

[Chelsea Handler]

So now when I hear, like, big words, I'll just do them.

[Katherine Law]

I just clarify. Perspicacious means very perceptive, so I'm just being a Cunt. By saying perspicacious. Because I love the way. Cause it's such a mellifluous word. There's another word.

[Chelsea Handler]

There you go.

[Katherine Law]

Euphonious. Mellifluous words that roll right off your tongue or that are fun to say. I love to say perspicacious is one of them. Like perspicacity. But you could say perspicacity. Perspicacity is another version of perspicacious. Right. You know, it's another tense, but it basically just means very perceptive. Yeah. Chicanery. Chicanery is something that just means like silliness and foul play. Not foul play. Like silliness and like hijinks. Like hijinks. Yeah. Like you're up to shenanigans. Chicanery. Shenanigans, yeah.

[Chelsea Handler]

Which I certainly had to Google after the first couple times you used it.

[Katherine Law]

Yeah, yeah. But I have like about 15 words that I rotate that I love, and then I throw in some new ones all the time. But I'm like you. When I hear a word, I don't know, I have to look it up immediately.

[Chelsea Handler]

Yeah, yeah. Well, we'll add that in and we'll just start doing a little segment at the end.

[Katherine Law]

Yeah, yeah. Vocab boards. That's cute.

[Chelsea Handler]

Yeah. Well, our first caller today is Dwayne, and it's a little bit of a long email, but no one loves a.

[Katherine Law]

Long email more than Katherine.

[Chelsea Handler]

And I cut them down. That's the thing, I cut them down. This is probably a third of what it was. So Dwayne says, Dear Chelsea, I'm a die hard fan of yours and have followed your career for decades. And I never miss an episode of Dear Chelsea. This podcast keeps me sane during my 30 mile commute each way to and from work. I'm 47 and an only child. My dad passed away suddenly of heart issues in 2004. He and my mom were married for over 30 years at the time of his passing. For the first few years following, she never had an interest in dating or finding another partner. Then she met Bob somewhere around 2015. At first, I didn't mind Bob. He was a little annoying because he always had to be a part of every conversation and topic. He's hard of hearing and refuses to get a hearing aid. He talks a lot about himself and has a story about himself for almost every topic. Even though he could be painful to be around, he seemed to care for my mom and treat her well. He moved into her house somewhere around six months into their relationship. I should mention Bob had supposedly been married twice. Eventually I came to find out that Bob was not just sometimes annoying, but he was also misogynistic, a know it all, dishonest, and quite frankly, an asshole. My mom had kicked him out after she had discovered he lied to her about being twice married. Turns out he was in the middle of a divorce from his third wife. Not to mention she caught him talking to a woman on a dating site. Jump ahead. About six months after she kicked him out and I heard through the grapevine that she was back with him. I confronted her and she came clean that he was back in the picture. I voiced my concerns and said how much I disapproved and she could find someone so much better. He was trying overly hard to get my approval by forcing conversations, no matter if it's a topic he knows I have no interest in. I try to have the minimum interaction with him as possible and still remain respectful. But I'm the type of person who can't hide my thoughts and I speak my mind. I will give him credit that he does accept me for being gay, but honestly, it's one of the very few things about him that I will say is positive. They sleep in separate bedrooms. And when I ask my mom why she stays with him, she says his company is better than nothing. I've even tried to get her to move either close to me and my husband, but I haven't had much luck with her being 80 and soon to be 81 in a couple months. I don't want anything to happen where I regret something or that Bob takes time away from me and my mom. What can I do to either convince her to leave him, leave him by moving us, or just get the situation to change, but that means he would have to change. Additionally, I'm going to stay with them for a bit after she has hip surgery in a couple months. How am I going to survive that much time with Bob? Dwayne.

[Katherine Law]

Hi, Dwayne. How are you? Hi.

[Dwayne (Caller)]

Good. How are you? Thanks for taking my question. Yeah, I appreciate it.

[Katherine Law]

Of course, of course. Do you really think there's a reality of your mom leaving him?

[Dwayne (Caller)]

Sometimes, sometimes not. So there's. So there's times that she actually will be. She'll come to come visit us in Washington and she doesn't tell him that it's planned until like a week before she's gonna leave. And she'll. She will know him for a while and stuff. And so she does some stuff to annoy him because of how much he annoys her sometimes and stuff.

[Katherine Law]

Too.

[Dwayne (Caller)]

So I think she needs that extra push and stuff. But she's also in the town she grew up in, and that's also where my dad is buried and her parents are buried and her brothers and stuff, too. And her. She has one brother still there, but she does have one brother over here in Washington as well. I'm very protective of my mom, and so one of the things that breaks my heart is that she is more in, like, a roommate type of situation, and that she basically lives in her upstairs. She's always doing, like, diamond painting, crocheting, and stuff like that, but doesn't interact with him as much. And so it's more of a lonely thing. Definitely don't know how to. I don't know how to kind of break that or try to get her out of something that is more just where she feels kind of stuck, I guess, or that it's just better than nothing.

[Chelsea Handler]

This is a situation where I feel like going into a senior living situation. We're not talking necessarily assisted living, although she might need that, like, with the hip surgery coming up and everything, but like a Sun City. Like, is there anything like that by you?

[Katherine Law]

That.

[Chelsea Handler]

I mean, those are places that are designed to help you continue to have social interaction. And, like, not just with one person, but there's activities all day long. She can participate as much or as little as she wants. But you're in a community of other people who are like you, and you don't just have this one person who's, like, living in your house.

[Dwayne (Caller)]

Yeah, that's. That's a good idea. I've. Me and my husband have talked about that, but I haven't really brought it up to her necessarily.

[Katherine Law]

Well, I mean, if she's getting this hip surgery, listen, if that's even on the table, that she would be open to, like, leaving him then. And getting this hip surgery would be the perfect kind of break. Cause she could move into one of these facilities. You could move in with her while she's healing, and that could be like, her introduction into one of those places, into, like, a retirement community. But, like, that's. I. I don't know how realistic that is. I mean, that she. You're gonna convince her to. Because there's other company to be had. Absolutely. If she were a lot younger, I would say go for it. I would say go for it at any age. But I mean, it. It just might not be a reality. Like, she is living with a roommate. And if that's the. Meet a bunch of other people, that could be much More, you know, fun to be around and have like. And play games with and socialize with. If she's not sleeping in bed with him either. I mean, that's pretty common for older people at this point. I mean, nobody likes to sleep with each other at this age.

[Dwayne (Caller)]

Yeah, they don't really have a whole lot in common.

[Katherine Law]

Yeah.

[Dwayne (Caller)]

So for him, it's all about sports. My mom couldn't care less about sports.

[Katherine Law]

Right.

[Dwayne (Caller)]

And so she likes her Hallmark movies and stuff like that.

[Chelsea Handler]

I want to hang out with your mom. Diamond painting and watching Hallmark movies.

[Katherine Law]

Why don't you go and. Did you say there was a place that you saw, like, a retirement place that would be appealing for her? Is there any place, like, she. Would she move where you guys are? I know you said, like, half her family is buried there.

[Dwayne (Caller)]

Yeah. So I would really like her to. I don't know how realistic it is that she would actually pick up and move. She owns her home, so it's a matter of selling her house and everything, which I don't think she's opposed to, because there is a retirement community back in her town that she has told me before that she wouldn't mind going to. And it's a senior community, and they have ones that are like condos and cottages and stuff. So it's not full on, like, apartment. It's almost like a Grace and Frankie type of place in a way.

[Katherine Law]

Well, that would be great. I mean, but would he want to come with her to that if that were an option? Because even then she's surrounded by other people. You know what I mean? So that would open up her socializing.

[Dwayne (Caller)]

Yeah, it's possible that he would want to, because it is her house that they live in. That's kind of the other thing that I'm also afraid of, is that if something does happen to her, how much of a nightmare is it going to be with him of wanting to try to take stuff that isn't his or try to say that there was common law.

[Chelsea Handler]

And they're not married, right?

[Dwayne (Caller)]

No, they're not.

[Chelsea Handler]

Okay. You got to see an elder law attorney, not just an estate planner, but an elder law attorney, and they'll help you put protections in place to, like, you know, follow the bloodlines and that sort of thing.

[Katherine Law]

You should. All of this hip surgery is a perfect excuse to do all of this stuff. You know what I mean? Like, you want to get everything in order in case something goes wrong. It won't. But as a responsible son, this is what you have to do for her. I'VE spoken, you know, get your ducks in a row that you've spoken to an elder law attorney, you've spoken to an estate planner. You want to make sure that if anything happens to her that Bob doesn't. Is his name Bob?

[Dwayne (Caller)]

Yeah.

[Katherine Law]

Bob doesn't get all of her money, doesn't get her house. She doesn't want that, I'm sure, you know, and then open up the conversation to her potentially, or what I would love to see happen is for you to move into a retirement community where you could actually have some friends around who have more in common with you than Bob does. And more importantly, do you really want to be in this relationship with Bob at this point? Like, don't. What about transitioning you into this retirement community? I'll stay with you. We can sell your house, we can get you better while you're recovering from hip surgery, and we can kind of move your life into a different direction, which I think would be more positive for you. I mean, there's no harm in suggesting all of these things, right?

[Dwayne (Caller)]

Yeah. And what I have suggested to her is we have a fairly big lot and we were talking about, you know, getting her a tiny home and putting it on our. On our property where she was basically our neighborhood in a way. She still has independence. We're right there. We have a dog that she calls her grandpuppy and stuff. So she would be all in her glory with him and stuff, or even adding on to our house and stuff too. But me and my husband have talked about the senior community, but I never really approached her. And I think that makes a lot of sense, though, with having excuse of her hip hop hip replacement surgery as part of that. This is a great place for. For you to heal. You be able to have like a community of people around that you'd be able to make friends with at the same time and not just be sitting.

[Katherine Law]

Around bored and nurses and stuff. See what their nursing situation is like, if do they have that on? Some of those places do and some of those places don't. But I think for this, for the specifics of this, like, you're not. You're not pawning her off to these people that you want to make clear you're going to be involved within whatever happens. Even if she moves into place, you're still going to be there to help her with her hip after.

[Chelsea Handler]

And at 80, like, she doesn't necessarily even want to be taking care of a whole house. Like, that becomes a lot of work for someone as they age. So this, I mean, Just present all these options. Like, we can talk about a tiny home. We can talk about, like, let's go see this place that's nearby you while I'm here. Like before you get your hip surgery. Like, there's a lot of conversation you guys can have.

[Dwayne (Caller)]

Right? Yeah, that's. That's a good idea. I think that that's probably a good way to go. And there's the option of if she wants to stay there, that there's one there that she has shown a little bit of interest in from like a few years ago that she mentioned. And then even in my area, there's quite a few around my area. Not far away, I would say within anywhere from 1 to 5 miles maximum from our house.

[Katherine Law]

Yeah, great. So get this stuff going. This hip surgery is actually a blessing in disguise in terms of all these conversations. And then also get the estate planning sorted so that that guy doesn't, you know. You know. Cause she's gonna wanna be reminded of that too.

[Dwayne (Caller)]

Right?

[Katherine Law]

Yeah, she doesn't want that to, you know, happen. Like, if anything were to happen, she does definitely doesn't want him to get her house based on what you're telling us.

[Chelsea Handler]

Yeah.

[Dwayne (Caller)]

Yeah. Right, Right. Yeah, that's a good idea.

[Chelsea Handler]

Thanks, Wayne.

[Dwayne (Caller)]

Thank you. I appreciate it so much. I really am thankful for the advice and the help and even. Not even just my question, all the advice that you guys give other people, I find so some of it, you know, pertaining to me a little bit. I take a little bit of that every episode.

[Katherine Law]

Oh, love that. Love that. Well, thanks for calling in and you're a great son. I'm glad you're taking care of your mom. Okay.

[Dwayne (Caller)]

Thank you.

[Katherine Law]

Take care. All right.

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Bye.

[Dwayne (Caller)]

Bye.

[Chelsea Handler]

Well, we'll take a quick break and wrap up with a quickie.

[Katherine Law]

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[Katherine Law]

Of perspective and we're back, we're back, we're back.

[Chelsea Handler]

That was so fast. Okay, Ann says. Well, she writes in her subject line is Picking favorites. Dear Chelsea, I love favorites. I live in Pennsylvania and have a large family who lives all over the country. My sisters both have kids. Since my older sister had her kids first, I feel a strong bond with three of her four. Three of her four kids. The fourth is just okay. And I don't feel it as much with my middle sister's oldest child. I just came home from visiting my middle sister's newborn with her new husband, and I've never experienced that sort of baby fever and love before. I'm 30 years old for reference and child free, living my best life. I wonder if part of the reason I'm closer with my oldest sister's kids is because I was younger and had fewer responsibilities, so being an aunt was more of a priority and I would visit home all the time. Now I have a life and I'm tired. Since meeting my freshest nephew. I have a newfound desire to spend more time with my family and but I want to be a better aunt to my sister's oldest daughter. Whom is the least favorite? How do you spread the love and not choose and subliminally advertise favorites?

[Katherine Law]

Anne well, I would just know you've already chosen your favorites. Like, okay, that's obvious, but go and put in the time to the one that you haven't that has been neglected. She'll appreciate that. Go spread the love and make an actual effort to be like, okay, you know what? I fucked up here. I didn't give her the right amount of energy. I I had my other favorites. It was very obvious to everyone and I'M gonna go put in the time and effort now. Absolutely. It's never too late, you know what I mean?

[Chelsea Handler]

And especially. Cause they're growing and changing.

[Katherine Law]

Yes.

[Chelsea Handler]

And getting more interesting.

[Katherine Law]

Make sure that she knows you're making the effort. You know what I mean? Keep showing up and if you don't get the response you want, that's okay. But just keep making yourself available to her.

[Chelsea Handler]

Yeah.

[Katherine Law]

And like little gestures.

[Chelsea Handler]

One on one dates and gestures or.

[Katherine Law]

Friendly one on one on one dates. I guess noticing what they like.

[Chelsea Handler]

Yes.

[Katherine Law]

You know, getting her little trinkets of or gifts of stuff that you know she likes or you know, if there's a movie or an actress that she likes, making sure you send her clips of that person on, like DMs, stuff like that. Or take her to movies when they come out. Like, I know you really love Marvel. I'm gonna take you to this movie. You know, when it comes out, like, just pay attention to what her interests are and try and figure out a way for you guys to connect.

[Chelsea Handler]

Yeah. You're such a good auntie.

[Katherine Law]

Okay, thanks, guys for listening. Make sure you go to chelseahandler.com to find tickets for my standup shows for the rest of the year. There's only like or six, so come see me. Come see me live. It's going to be a good time, guys. Bye.

[Chelsea Handler]

Do you want advice from Chelsea? Write into dearchelseapodcastmail.com Find full video episodes of Dear Chelsea on YouTube by searching earchelseapod. Dear Chelsea is edited and engineered by Brad Dickert executive producer Katherine Law. And be sure to check out our merch@chelsea handler.com.

[Katherine Law]

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[Chelsea Handler]

This is an I Heart podcast.