A Late Bloomer with Kaitlin Olson

Summary

Dear Chelsea – Episode Summary

Podcast: Dear Chelsea
Host: Chelsea Handler
Episode: A Late Bloomer with Kaitlin Olson
Date: January 8, 2026
Guest: Kaitlin Olson

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Episode Overview

This episode welcomes comedian and actress Kaitlin Olson (It's Always Sunny in Philadelphia, Hacks, High Potential) to join Chelsea Handler and co-host Kathryn Law. The episode’s main theme explores being a “late bloomer” in life and career, working motherhood in Hollywood, owning your quirks, and offering real and empowering advice to listeners on everything from parenting to pursuing dreams in adulthood. The conversation blends personal stories, behind-the-scenes Hollywood anecdotes, and heartfelt (often hilarious) listener advice.

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Main Discussion & Episode Highlights

1. Life and Career Milestones (03:51 – 13:05)

• Chelsea shares the joy and surprise of feeling better at 50 than at 35.
  “Every woman that is listening to this, you need to know how much better everything keeps getting.” [03:51]
• Kaitlin reflects on 20 years of It’s Always Sunny in Philadelphia, the odd longevity of the show, and the blessings it brought—including meeting her husband, Rob McElhenney.
  “It's the best thing that ever happened to me. But also, you don't want to overstay your welcome.” [06:28]

Behind-the-Scenes Romance & Family

• Kaitlin details how she and Rob McElhenney began their relationship in secret on the set, humorously describing flirting and “hammering him with it” [06:52].
• She discusses her home birth experiences—going to a baseball game while in labor for her first child and enduring a tough 2.5-day at-home labor for her second. “Three days into that… I fucking hate myself. I hate midwives. I hate babies. I hate everyone.” [10:52]
• Chelsea reacts to the ordeal:
  “Oh my God, what a nightmare. Two and a half days of labor. You were laboring at home for two and a half days before you had the baby?!” [11:25]

2. Characters and Lessons from TV (12:03 – 16:46)

• Kaitlin talks about her role as DJ in Hacks and how sometimes tough parents can serve as a model for parenting by contrast:
  “She’s just going to look at whatever Deborah did and do the opposite.” [12:03]
• Balancing multiple shows: Kaitlin credits the flexible schedule of Sunny but admits “it's starting to get to me” [13:05].
• Memorable moments on set: Kaitlin says the most fun Sunny episodes are the insane ones involving stunts, like being set on fire or drowning in a bog [13:34].

Vanity and Family

• On who’s more vain (her or Rob):
  “Me. He's not that vain. There are other men on my television show that are a little bit more vain.” [14:33] (Names Glenn Howerton)
• Parenting: Her older son (15) is obsessed with Sunny and started sneaking scripts at a young age. Kaitlin says she’s the funnier parent, Rob’s the smarter one [15:34].
• Humor at home: Kaitlin delights in her sons’ wild antics, reflecting on the difference between her sons’ personalities and penchant for naked trampoline escapades [15:51–16:46].

3. Insights on Relationships & Neurodiversity (17:03 – 18:45)

• Kaitlin discusses Rob’s neurodivergence and how it explained quirks in their relationship (like Rob going silent mid-conversation):
  “There's so much going on in his brain at all times.” [17:25]
• On the challenge of balancing work and home, Kaitlin confesses enjoying being a part-time “dream mom” while Rob shoulders heavy lifting at home:
  “Anybody can be a really excellent parent for three hours at a time. Rob's really doing the heavy lifting right now.” [19:03]

4. Pets, Parenting—and Chunky Babies (19:38 – 22:41)

• Chelsea and Kaitlin swap pet stories, with Kaitlin’s two dogs and a mellow, floppy cat who integrated seamlessly.
• The duo bond over preferring chubby babies:
  Chelsea: “I want a big nugget. If you have a baby on a plane...the chunkier the better.”
  Kaitlin: “It's like a twig. It's too fragile.”
  Both lament skinny babies as not “scrumptious.”

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Listener Advice Segment

5. Keeping Your Ex’s Last Name (29:03 – 30:32)

• Listener Nicole is recently divorced, wants to have another child via sperm donor, and wonders if she should keep her married name for the child.
• Advice:
  • Chelsea and Kaitlin firmly encourage keeping the last name:
    “That's not an engagement ring, right? That's your last name. And also, who cares about the ex in laws? Keep the name.” (Kaitlin, [29:59])

6. Late-Blooming DJ Fears (31:10 – 38:38)

• Listener “Redneck Kitty” (31) feels like a late bloomer as a new DJ and battles self-doubt and comparison fears.
• Key Advice:
  • Kaitlin: “My 30s were way better than my 20s…You're just getting started.” [34:13]
  • Chelsea: Write down all you’ve accomplished to remind yourself of your growth—“You're not letting life happen to you. You're happening; you're making your life happen for you.” [35:00]
  • Redneck Kitty shares her first EP release.
    “You made a song—that’s number one on your list!” (Chelsea, [37:53])

7. Parenting a Strong-Willed Daughter (39:45 – 42:17)

• Listener Jen struggles with rewarding her strong-willed 7-year-old daughter, who demands treats for good days.
• Advice:
  • Teach financial responsibility by going through receipts, offering non-monetary rewards like attention or board games, and making treats special rather than routine.
  • Kaitlin: “Come up with little jobs for her where she can save money…and then when she saves up enough…go to Starbucks.” [41:48]

8. Navigating Friendships as an “Old Soul” (43:32 – 51:22)

• Listener Kristen, 23, feels disconnected from peers her age and better relates to older women.
• Advice:
  • Chelsea: “Go where the light is.” Friendships can cross decades.
  • Kaitlin: Don’t obsess over being ghosted.
    “Just figure out what friendship means to you…and enjoy it, even if it’s with older women for a time.” [47:20]
  • If bluntness is your nature, embrace it.
    “Don’t edit your personality. Being blunt and being direct—you’re gonna find your people.” (Chelsea, [51:22])

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Memorable Quotes

• Chelsea Handler [03:51]:
  “Every woman that is listening to this, you need to know how much better everything keeps getting.”
• Kaitlin Olson [06:28]:
  “I have zero mixed feelings about it. I met my husband. I've got two kids. It's the best thing that ever happened to me.”
• Kaitlin Olson [12:03]:
  “DJ…is gonna end up being a real good mom. ‘Cause she’s just gonna look at whatever Deborah did and do the opposite.”
• Chelsea Handler [35:00]:
  “You're not letting life happen to you. You're happening; you're making your life happen for you.”

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Advice Segment Timestamps

• Advice on keeping your ex’s last name: [29:03 – 30:32]
• “Late Bloomer” DJ Question: [31:10 – 38:38]
• Parenting a strong-willed daughter: [39:45 – 42:17]
• Friendship and being an ‘old soul’: [43:32 – 51:22]

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Notable Moments

• Kaitlin and Chelsea's playful banter about female aging, vanity, and beauty standards (03:51–05:37, 14:33–15:30)
• Kaitlin’s candid and comical take on tough home birth:
  “Let me be very clear. It was terrible. Bad idea.” [22:38]
• Both women encourage listeners to live authentically, take risks, and unapologetically own their quirks for personal fulfillment.

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Final Thoughts

The episode strikes a blend of empowerment, humor, and vulnerability. Kaitlin Olson shines as a guest—offering wisdom about starting late, parenting without shame, and pushing through daunting career transitions. Chelsea Handler and Kathryn Law support listeners and each other with warmth, wit, and sharp, loving honesty.

For anyone feeling “late” in life or doubting their unique path, this episode is a pep talk from wise, hilarious friends who’ve seen it all—and say it’s never too late to find happiness and fulfillment.

Transcript

[Chelsea Handler]

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[Kathryn Law]

I can Hear your Voice, Ms. Critics Choice Award host. You absolutely crushed it.

[Chelsea Handler]

Oh, thank you. I had such a good time at the Critics choice Awards. I can't believe how. I can't believe my dresses and my tux and the way I looked. I was like, what? I saw pictures of myself. I'm like, oh, my God. I can't believe that I'm 50 years old and I look better than I did when I was 35. Every woman that is listening to this, you need to know how much better everything keeps getting. Like, oh, my God, my body, my face. Everything looks better. I'm so pleased. And I have to tell you, I love the way you look in a tux.

[Kathryn Law]

You know this already, but, like, I love it.

[Chelsea Handler]

That was my nod to Diane Keaton, but I loved it, too. I felt like a real fucking bitch in that tux.

[Kathryn Law]

That's the best way.

[Chelsea Handler]

Yeah, it was super fun. I'm here in New York City getting ready to do some press. I'm doing Kelly Clarkson and I'm doing Jimmy Fallon tomorrow night to promote my high and mighty tour. Tickets are on sale, people. Get your tickets. The tour job's off in D.C. in February, so get your tickets. And we have a fun guest today. You know her from it's always Sunny in Philadelphia hacks and her new show, high potential. So please welcome Caitlin Olson.

[Kathryn Law]

Hi.

[Chelsea Handler]

Oh, look who's here. Hi, Caitlin Olsen.

[Kaitlin Olson]

Oh, my God, I can't believe I've never met you before. This is crazy.

[Chelsea Handler]

I know. I was watching you in high potential the other night doing your detective work. I'm like, have I met her and not remembered? And I'm like, no, I would remember your energy because I love your energy. Every time you're in a scene in any of the things that you do, you light up the room. And that is just like. That's so sweet. No, I mean it. I mean it. You're just so light filled and I just love that about you. So congrats on being light.

[Kaitlin Olson]

Oh, my. Thank you very much. I've never been congratulated on that before and I really appreciate it.

[Chelsea Handler]

Well, there's a lot of things that are going to happen today that have never happened to you before.

[Kaitlin Olson]

I can't wait.

[Chelsea Handler]

First of all, I can't believe that's always Sunny has been on for 20 fucking years. Or 20 seasons. Is it?

[Kathryn Law]

20 years, right?

[Chelsea Handler]

20 years.

[Kaitlin Olson]

20 years, yeah.

[Chelsea Handler]

So you. That's crazy. That's like two lifetimes of television.

[Kaitlin Olson]

It's getting weird. Like for a few years ago, it was exciting. We're like, oh, we're breaking records. And now it's like, well, now we're just old and weird.

[Chelsea Handler]

Yeah, it is. It's probably. I mean, I'm not saying it is getting weird, but I can understand what you're saying about it getting weird. I mean, I think the main reason you have to be always grateful to that show is because you met your husband. So, like, if. If it weren't for that, then you can't have any mixed feelings about that.

[Kaitlin Olson]

I have zero mixed feelings about it. I met my husband. I've got two kids. It's the best thing that ever happened to me. But also, you don't want to overstay your welcome. You know what I mean? So at what point am I like, I should probably Irish exit? Should I just leave the show and not tell anyone?

[Chelsea Handler]

Oh, I didn't know if you're talking about your marriage or the show, but copy that.

[Kaitlin Olson]

Either way. Either way. They both would be very exciting and a fresh start.

[Chelsea Handler]

You guys met the first year and you obviously hooked up right away. Is that right? Or you tell us what happen.

[Kaitlin Olson]

I mean, in the scheme of things, it was right away, but it felt like a lifetime. He loves the story that I definitely was interested in him and took every opportunity to be at a party where there was alcohol, to find myself, like, touching him with some part of my body, just getting really? In his space. And he was like, okay, this is unprofessional. And I was like, excuse me, I'm flirting with you. And I didn't understand it. And then I just hammered him with it. You know, I just.

[Chelsea Handler]

And then you hammered him on the alcohol, right?

[Kaitlin Olson]

Yeah, and then I hammered him. Well, he hammered.

[Chelsea Handler]

He hammered you in the end.

[Kaitlin Olson]

He hammered me. Let's just be very clear. There was a flip that switched.

[Chelsea Handler]

My friend said that to me the other day, and I was staying with my friend Kat, and she's like, did you ever bang that guy? I go, what? Who talks like that? I go, first of all, I go, bang him. And she goes, yeah, you never say bang. I go, no, I don't. I don't ever say that. By the way, you're the one getting banged. I'm not banged. She goes, that depends how you look at it. I'm like, well, I'm definitely not banging men.

[Kaitlin Olson]

When I have sex with them, they're banging me. Thank you very much.

[Chelsea Handler]

So your husband's Rob McElhenny, right? But he goes by Rob Mack now. Did he. Did he change his name?

[Kaitlin Olson]

Yeah, he made a big thing about it. He changed his name, and now he's Rob. Mac and I have two kids who are stuck with McElhenney, so we don't talk about.

[Chelsea Handler]

Well, he was actually, originally Rob McElhenny III. So your kids. Right. Isn't that his real name?

[Kaitlin Olson]

There's a whole thing. His name has been a subject of great grief for him our entire marriage, and I think his entire life. There's a lot of misunderstanding, I think on his birth certificate, it's just Robert McElhenney, but they put a space between the Mac and the Elheny, I think, accidentally. And so that's been really fun for me, trying to figure out what my. Cause I have that technically as my last name. I don't use it, but it's, like, on my passport and stuff. But then his dad and his grandpa were Robert, but they have middle names and he doesn't, so he's not technically a third. But I don't care anymore is the point. I just bored myself for the last 30 seconds trying to. Who cares? Rob Mack. That's his name. It's easy. He's great. Again, we're stuck with McElhenny, but that's a subject for another time.

[Chelsea Handler]

So how did you keep it a secret from the other cast members until you decided to go public with your relationship?

[Kaitlin Olson]

Well, we were just in our trailers a lot And I don't know, we thought for sure that they were gonna find out because we thought it was really obvious because we were being very flirty and we travel for work back then. This is before we had kids. So we would be staying in hotels in Philadelphia and New York, and we'd always end up in each other's hotel rooms and, like, getting off on the wrong floor with two cups of coffee and be seen by them and be like, I don't know. I. I'm not great with floors. I. I don't know. We. They. They had no idea, though. We kept it secret for a whole season.

[Chelsea Handler]

Wow. Well, that's impressive, especially in Hollywood terms. You know what I mean? I mean, those things are pretty obvious.

[Kaitlin Olson]

Staying together for a whole season is impressive.

[Chelsea Handler]

Well, staying together for 20 seasons is even more impressive.

[Kathryn Law]

I know.

[Chelsea Handler]

I read that you went to a baseball game while you were in labor.

[Kaitlin Olson]

Well, I was planning a home birth. That's. Listen, I apologize already. This is gonna be irritating. I was planning a home birth. So my midwife was like, you're gonna go into labor. You're gonna go for a walk. You're gonna go grocery shopping. You're gonna be in public so that you can't have a meltdown. You're pull your shit together, and you're just gonna walk around. We're not gonna lay down on a bed. And so I started feeling like I was having contractions. And we were supposed to go to this game. And I was like, you know what? I'm supposed to go on with my life. Let's go to the game. So we climbed in, I folded myself into his. He had that original Tesla that looked like a little toy car that was like six inches above the ground. I folded my body into that, and we went to the game. And I think I made it seven innings. Something like, I don't even remember. But at a certain point, I was, like, throwing up and having diarrhea in the bathroom. And I was like, probably time to go.

[Chelsea Handler]

And then what happened? Did you have the home birthday?

[Kaitlin Olson]

I did eventually. Yeah. At some point the next morning, did you have two.

[Chelsea Handler]

Do both of your kids are home births?

[Kaitlin Olson]

So I got pregnant the second time, and I was like, oh, no, I should. I probably have to do that again so that they don't, like, find out. And that turns into a therapy thing. Like, well, why'd you have me at home and then go straight to the house? So I decided to do it again, not. Cause I wanted to. And three days into that, when I was like, I fucking hate myself. I hate midwives. I hate babies. I hate everyone. And I did. I had him at home.

[Chelsea Handler]

But three days into. What? What do you mean?

[Kaitlin Olson]

Three days into was like two and a half days of labor. It was a lot. It was a long time. The second one I thought was gonna slide right out.

[Chelsea Handler]

That's what I was promised. But oh, my God, what a nightmare. Two and a half days of labor. You were laboring at home for two and a half days before you had the baby?

[Kaitlin Olson]

Yeah. At one point we drove over the canyon behind garbage trucks. Cause it was garbage day in the backseat of my midwife's Prius to go to the gynecologist to check something out just to make sure. And everything was fine. So then we drove back over the can. It was. A lot happened in those two and a half days. Not a baby coming out.

[Chelsea Handler]

Wow, wow, wow. Tell me what playing the character you play on Hacks has taught you about being a parent. Or what has it taught you not to do about being a parent?

[Kaitlin Olson]

Yeah, I don't know that I take any advice from dj. I love her, but listen, dj, I think is gonna end up being a real good mom. Cause she's just gonna look at whatever Deborah did and do the opposite.

[Chelsea Handler]

Which is always a good pointer. When you have great parents, it's impossible to replicate that exactly. But when you have bad parents, it's almost a natural instinct to do the opposite of what they've done.

[Kaitlin Olson]

Yeah. What a blessing to have a horrific childhood, you know? Cause then you know exactly what not to do.

[Chelsea Handler]

That's a great. That's a great way to look at it. I wanna know how you managed to be on. Starring in two shows also on Hacks. How do you. Who's your agent? How did you. How are you able to negotiate these kinds of deals?

[Kaitlin Olson]

The good thing about Sunny is that we don't have a set time of year that we shoot it. We kind of shoot it whenever everyone's available. So we can move that around and sort of make it work. It's only been. This is my second year of kind of working literally every day nonstop. It's starting to get to me. I'll be. I'll be honest.

[Chelsea Handler]

It's a lot of work.

[Kaitlin Olson]

You know what it is? It's. It's a lot of work. And it's working through now a second spring break and a second summer vaca break for my kids. So I kind of feel like I should probably be going on vacation with you guys at some point in the next Couple of years, right?

[Chelsea Handler]

Absolutely, Absolutely. Especially because High Potential is essentially a procedural. So that's a lot of hours.

[Kaitlin Olson]

It's a lot of hours, yeah.

[Chelsea Handler]

I want to know about, like the most fun memory or the most fun day of shooting that you ever had on It's Always Sunny.

[Kaitlin Olson]

People ask this, and first of all, I can't even remember all the episodes, but anytime I'm like, lit on fire or I'm addicted to drugs or I've been thrown off a building, those are always the really fun ones. You read it. I love when people are like, do you ever read anything and be like, absolutely not, I'll never do this. I was like, no. Who's that asshole? If they write me, like, big funny stuff, I'm so excited. There's a lot of fun, like, stunt stuff that I get to do on Sunny. Oh, you know, there was the one where we Dee drowns in a bog. That was horrible. That was at like 2 o' clock in the morning. Yeah, anything like that. That's insane.

[Chelsea Handler]

Yeah. Well, I think that's what comes true in your. When I'm talking about your ebullience, I'll use that word, my favorite word.

[Kaitlin Olson]

Ooh. I don't know what it means, but I just inferred and I think I get it.

[Chelsea Handler]

Yes. That comes through in your willingness to just kind of be silly and outrageous. You know, like, it's when people take themselves too seriously, you don't see that kind of shine through.

[Kathryn Law]

Effervescence.

[Chelsea Handler]

Yes, an effervescence.

[Kaitlin Olson]

Thank you.

[Chelsea Handler]

You're so welcome. Who's more vain, you or Rob?

[Kaitlin Olson]

Me. He's not that vain.

[Chelsea Handler]

No.

[Kaitlin Olson]

There are other men on my television show that are a little bit more vain.

[Chelsea Handler]

Do you want to name names?

[Kaitlin Olson]

Glenn.

[Chelsea Handler]

What about your kids? Do you let your kids watch any of your shows or are they too little?

[Kaitlin Olson]

No, they're not. They're 13. My older one just turned 15 and he has been sneaking Sunny scripts since he was about 7 or 8. We'd find him in bed reading Sonny scripts and we were like, well, this is bad. And then a few years ago, he started. Like, we would start, we would show them different chunks of episodes and he's just obsessed with it. And now it's off the rails. He's like, he's seen every episode. He thinks it's amazing. And I love that because it is a really funny show. But when you're 15, you gotta kinda fine tune that. I mean, I'll pause things all the time. He'll say stuff all the Time where I'm like, whoa, that's not funny. And then we have to have those conversations in time. He's going to be a very, very funny young man who's.

[Chelsea Handler]

Yeah, who's funnier, you or Rob in the family dynamic?

[Kaitlin Olson]

I'm funnier.

[Chelsea Handler]

You're funnier.

[Kaitlin Olson]

And he'll tell you that. Yeah, he's smarter. He identifies himself as more of a writer, producer. He loves acting. But he would say that I'm funnier.

[Chelsea Handler]

Okay, well, that's good. That's smart. And which one of your children is more like you? Is there one that's more like you and one that's more like him?

[Kaitlin Olson]

Yes. The older one who's sneaking sunny episodes is more like him, and the younger one is more like me. And he legitimately cracks me up. The other day, I got home, they had all had dinner. They're gonna kill me. They'd had dinner, and they were outside. We still have a trampoline in the backyard. My older one was spraying down my younger one, who was jumping on the trampoline naked doing flips, while Rob was taking slow motion video of him flipping makeup.

[Chelsea Handler]

That's why I went to my dermatologist the other day, and she was showing me her group chat between. You have two boys? Yeah, yeah. She was showing me her group chat. She has four kids, three boys and one girl. And she was. I was like, this is so disgusting. Like, the way that boys talk to each other, the way that they drag each other. The nudity, the farting, the flat. Yeah. The famous drag. It's all about assholes and penis. All about assholes and penis all the time.

[Kaitlin Olson]

There's so many balls. There's so many balls that I see on a daily basis. My little one, Axel, was chasing him with something, and he was like, don't do it. You do it. I'll strip. I'll strip. I swear to God, I'll strip. Cause my older one's a little bit more prudent. Leo's like, I'll just take all my clothes off. They crack me up. Balls are funny, you guys.

[Chelsea Handler]

Yeah, balls are funny until they're not. I think Rob talked about being. Finding out he was neurodivergent. Like, when you found that out. I always find this to be fascinating. Did any of his. The aspects of his relationship, or, I mean, aspects of his personality within your relationship.

[Kaitlin Olson]

Click, yes.

[Chelsea Handler]

Like what? What kind of stuff?

[Kaitlin Olson]

I remember going, oh, that's why, like, we would be in the car, just the two of us, like, talking about something, and then he would just go silent, like, even while we were dating. And I was like, does he know I'm still in the car with him? Like, he could just be completely in his own world. And I'm like, I'm not good with silence. I'm a person who has to, like, fill it, or let's have a. Or turn the music on or something. But what are we doing sitting here not talking? And I was like, oh, there's so much going on in his brain at all times. Like, he can easily be in a conversation with me and then just absolutely shut me out. And I'm, like, trying to pick up the pieces of what just happened. That was one thing. There's a million of them, though. But he's also, like, very prolific. He's super, super smart. And he's constantly coming up with ideas or business ideas or show ideas or doing things a way they've never been before. It's. It's pretty fascinating. It's very impressive. Yeah.

[Chelsea Handler]

He probably misses you. Doesn't he want more time with you with all of your responsibilities? He does.

[Kaitlin Olson]

They all miss me. It's very sweet, but it's one of those things, too, where it's like, he loves me a lot these days because I'm not around. I'm like, this totally works. I'm off doing my thing. Our relationship is great. You're missing me.

[Chelsea Handler]

Yeah.

[Kaitlin Olson]

But, yeah, it's exciting when we get to see each other, but I'm home, to be fair. Like, I only work. They have me for 11 hours here, so plus drive time. Like, I'm home for evening, so we spend time together at night.

[Chelsea Handler]

Well, then maybe it is the perfect schedule.

[Kaitlin Olson]

Yeah.

[Chelsea Handler]

You know?

[Kaitlin Olson]

Yeah, it's great. I just need a vacation every once in a while, and we're fine.

[Kathryn Law]

Yeah.

[Chelsea Handler]

And then you get to get all your kinks out on set, like, get all of your energy out. And that way you can be, like, you know, a full, complete mother when you get home, you're not there all day dealing with them. I like that schedule.

[Kaitlin Olson]

I love it. Yeah. Anybody can be a really excellent parent for three hours at a time. Rob's really doing the heavy lifting right now. I come home, and I'm just a dream. Like, the best mom ever.

[Chelsea Handler]

Yeah. That's the spirit. I always think about, like, mothers and how people handle stuff, especially in this business, because there's so much to deal with, you know? And I could barely take care of my dog. I don't even really take care of my dog, to be honest. Today he Had a limp. And I just was like, who do I text about this? You know? I'm like. And then they're like, did anything happen yesterday? I was like, well, I was wrestling with him, so I'm probably the culprit, but I've always just.

[Kaitlin Olson]

I love your dog, by the way.

[Chelsea Handler]

Oh, thank you, Doug. He's so beautiful. He's so. And he's got these big, beautiful brown eyes. It really makes me appreciate brown eyes because as a blue eyed person, everyone in my family has blue eyes. So I always think of it's this weird childhood thing where I always look at blue. My parents both had blue eyes and all my siblings have blue eyes. And so I always looked at everyone with blue eyes like, that's home. And now that I have a dog that has these beautiful brown eyes, I'm like, that's home?

[Kristen]

Yeah.

[Kaitlin Olson]

You're like, there's some soul there. What's this?

[Chelsea Handler]

Yeah, he's definitely soulful. I feel like his voice, if he could talk, would be like Luther Vandross.

[Kaitlin Olson]

Absolutely, absolutely. And that big thick tongue.

[Chelsea Handler]

Yeah, yeah, yeah. And they have purple tongues. Chow chows. You know that they have those purple tongues. So everyone always wants to see that. And you know what's so sweet about Doug, actually? He's so sweet with children, which is something that, like, you know, it's such a nice feature for a dog. He knows when to be gentle with small children. Not with small animals, unfortunately.

[Kaitlin Olson]

That's okay.

[Chelsea Handler]

Do you guys have pets?

[Kaitlin Olson]

Yeah, we have two dogs and a cat. And they're all really good friends. Obsessed with animals.

[Kathryn Law]

Yeah.

[Chelsea Handler]

I always wonder how cats get along with dogs, but I guess it's happened. I guess I grew up and we always had our cats and dogs completely separate. Other people seem to be able to integrate, but.

[Kaitlin Olson]

Well, I think it depends on the cat. Rob didn't think he was a cat person for this reason. He's like, cats are all like, finicky. This cat, I rescued him and brought him home, got him neutered and defleed and all that. And we had like him in a room and he came out of the room and saw the dogs came running towards him and he was like, hey. And flopped on his back and was like, smell me. So I don't know, he just decided he was fine with that. Now they all play together. It's the best.

[Chelsea Handler]

And is it a fluffy cat or is it a skinny cat?

[Kaitlin Olson]

He's a white fluffy cat with a big fat, fluffy tail.

[Chelsea Handler]

Oh, yeah. Does he have a fat face? A fat Fluffy face.

[Kaitlin Olson]

Yeah, he's like, he's like, he's all fluff. He's like a big giant. And if you hold him like this, he just like flops on either side. He's fine with whatever, which I like. I need that. I need you to be fine with me manhandling.

[Chelsea Handler]

Yeah, yeah, yeah. I like to put animals on their back and then just kind of molest them, you know, I want the bodies. I like the fur and I like the meat. The bigger, the better the puffier.

[Kaitlin Olson]

Yeah.

[Chelsea Handler]

All of it.

[Kaitlin Olson]

Yes, all of it. Don't give me a skinny. I don't want to have to be fragile. I got to throw you over my shoulder and you're coming with me.

[Chelsea Handler]

That's how I feel about babies too. I prefer them to be oversized, you know, like I want a big nugget. If you want, if you have a baby on a plane or like, you know, then like the chunkier the better. If you see a skinny baby, it's like I'm not drawn to that. And I mean, we already know how I feel about children, but babies obviously get a pass because they can be so luscious and just scrumptious, you know, but when they're thin, I don't like that.

[Kaitlin Olson]

It's like a twig. Like it's, it's too fragile. I'm not, I don't want to be responsible for it.

[Chelsea Handler]

Did you have big babies?

[Kaitlin Olson]

Yeah, Big fat babies.

[Chelsea Handler]

I feel like thin people. I know you're very thin because even on camera you look thin. I feel like thin people have the fattest babies. It doesn't make any sense.

[Kaitlin Olson]

I don't know how it happened, but yeah, they were both almost nine pounds.

[Kathryn Law]

Oh God, these are big babies.

[Kaitlin Olson]

Yeah.

[Chelsea Handler]

That is a big baby. With your home birth, with your two and a half day home delivery system.

[Kaitlin Olson]

Yeah, yeah. Let me be very cleared. It was terrible. Bad idea.

[Chelsea Handler]

We're going to take a break and we're going to be right back with Caitlin Olson to get some. Take some callers. Fleur de Mal is a women owned fashion brand offering luxury lingerie, ready to wear dresses and body suits with a seductive, cool and refined design approach. They focus heavily on high end materials such as silk, French laces and modern technical fabrics designed to look elegant while remaining wearable and comfortable. One of their most popular pieces is the flared corset knit dress which has been worn by celebrities including Taylor Swift. It is known for its soft knit construction and corset inspired seaming that shapes the waist, making it a versatile option for daytime social events or evening outings. Their lingerie assortment includes seamless everyday bras as well as more fashion forward lace designs. The Seduce you plunge bra has gained notable attention and is frequently described as offering a boob job in a bra effect. Due to its shaping and lift, Florida Mal is positioned as a premium luxury brand with retail locations in SoHo, Williamsburg and West Hollywood. The full assortment of lingerie dresses, bodysuits and ready to wear can be [e-mail] for the first time ever, there has been a truly beautiful medical breakthrough. One shot makes you hot, but with terrifying consequences. In the new original series FX's the Beauty, the glamorous world of supermodels turns deadly as mysterious deaths draw in FBI agents and a shadowy billionaire who will stop at nothing to protect his empire from executive producer Ryan Murphy. FX's the Beauty premieres January 21st on FX, Hulu and Hulu on Disney for bundle subscribers. This episode is sponsored by BetterHelp. The new year doesn't require a new you, maybe just a less burdened you. And therapy can help more easily identify what is holding you back. Getting a fresh, unbiased perspective can help you better understand your relationships, your motivations and your emotions. Kind of like when people write into this podcast, Obstacles are bound to arise in everyone's life. It might be something as simple as trying to be perfect all the time or doubting your full potential, but working through these emotions with a therapist can keep them from putting your life on hold. You don't have to settle for feeling stuck. Give the therapists at BetterHelp a try. BetterHelp is one of the world's largest online therapy platforms, having served over 5 million people globally. And it works with an average rating of 4.9 out of 5 for a live session based on over 1.7 million client reviews. BetterHelp makes it easy to get matched online with a qualified therapist, so sign up and get 10% [e-mail] DearChelsea that's better. H-E-L-P.com DearChelsea. You know how some people meal prep their dog's food? That's not happening in my house. I can barely prep my own meals that don't involve tequila. Enter JustFresh from Just Food for Dogs. It's real food. No fillers, no preservatives. And the best part? It's shelf stable. That means it doesn't hog my fridge space and I could travel with it like it's a Carry on cocktail. Doug thinks he's eating filet mignon. And honestly, he may as well be because here's the thing. I would never put ultra processed garbage in my body, so why would I give that to him? His coat looks shinier, he has more energy, and honestly, he eats better than half the guys I've dated. And you know what? I'm fine with that. Just fresh from JustFood for Dogs is the only thing that makes sense for me. Being busy and unwilling to cook for anyone but my dogs. You can try it right now with 50% off your first [e-mail] no code needed. Convenience, fresh food, and one less thing for me to screw up. Hi guys. I have some very exciting news. I am always looking for companies to support that are ethical. And let's be honest, the phone companies we've all been stuck with are not that. You know, I travel constantly and supposedly I have international free roaming on Verizon, yet my phone bills are still 300, 400, and even $500 a month. It makes zero sense. So I switched to a company with actual ethics, Noble Mobile. And they pay you for staying off your phone. The more you unplug, the more money you save each month. And the most you'll ever pay is 50 bucks. Unlimited coverage when I need it, cash back when I don't. It was started by people I know and trust. So if you trust me and want to join my mission to stop being a phone addicted zombie, come along. Go to noblemobile.com Chelsea right now and try it for just 10 bucks. That's noblemobile.com Chelsea and we're back with Caitlin Alston, who is the she's on hacks. She's the star of high potential and she's on It's Always Sunny in Philadelphia. So you really can't miss her. Caitlin, what was the best? Before we take a caller, can you think of the best career advice that you've ever been given?

[Kaitlin Olson]

You know what? The best audition advice, which is basically career advice for me, was to make it your own and stop reading all of the character descriptions so perfectly and trying to be exactly what you think they want. Cause they don't even know what they want. Just read the material, make the material as good as you can in your own voice and switch it up. Just make it your own and then go in and have fun. And that was honestly, that was very freeing. Once you stop caring about like, oh, I wonder if they're gonna want this. They don't know what they want. They just want you to come in and be good that was the best audition advice I got, and I still do it.

[Chelsea Handler]

Yeah, yeah. You have to own what you're doing, right? You have to make it your own, and you have to make it personal to you. And that's really kind of the only way to set yourself apart in any sort of creative, I feel like any sort of creative medium, I think it.

[Kaitlin Olson]

Absolutely it. You can use that across the board. Just. Just do what you want to do. Be the best version. People like it great. If they don't, great, it wasn't for you anyway. You can't cram yourself into a box.

[Chelsea Handler]

Okay, Great.

[Kathryn Law]

All right. Well, are you ready to give some advice?

[Kaitlin Olson]

Yes.

[Kathryn Law]

Excellent.

[Chelsea Handler]

Excellent.

[Kaitlin Olson]

Always.

[Chelsea Handler]

Always. Me too. Me too, sister.

[Kathryn Law]

So our first question. This one's just an email, but this comes from Nicole. She says, dear Chelsea, I'm writing in with a bit of a unique circumstance and would love some guidance on this. I'm recently divorced and it's as amicable as it could have been. We share tween twins and co parent.

[Kaitlin Olson]

Great.

[Kathryn Law]

I kept my married last name because I hated my maiden name. I'm a veterinarian and everyone in town knows me as doctor Ex husband's last name. That name is my kid's last name, too. My ex was totally fine with me keeping the name and using it how I wanted, even in our separation agreement. Now comes the tricky part. My ex never wanted more kids, but I do. I'm in the process of freezing eggs and hope to use a sperm donor before I'm all dried up and my clock is ticking. I just turned 41. My ex is supportive of this, but do I give the potential new baby from donor sperm the last name of me and my kids? I feel weird. Not that my ex will mind too much, but I'm also thinking of his very traditional family who may find it offensive that I'm giving their name to a child that's not biologically theirs. That said, I want this child to share my current last name and the name my kids all have. Any advice, Nicole?

[Chelsea Handler]

I mean, that is your last name. When people divorce, does the husband have to give it back? Permission to give your name, to keep your name?

[Kaitlin Olson]

Like that's not an engagement ring, right? That's your last name. And also, who cares about the ex in laws? Keep the name.

[Chelsea Handler]

Exactly. Who cares about the ex in laws? I was gonna say you could ask them, but then I thought, no, wait, why even bother asking them? Who cares a shit?

[Kaitlin Olson]

We're never talking to them again.

[Chelsea Handler]

Yeah, and you also want your kids to all have the same last name.

[Kaitlin Olson]

Yeah. Yes. They're siblings.

[Chelsea Handler]

That's your argument for that? If anyone comes to you or comes for you, I should say about. About passing that name along.

[Kathryn Law]

Yeah.

[Kaitlin Olson]

Especially if the ex husband is okay with it.

[Kathryn Law]

Yeah, yeah, yeah.

[Chelsea Handler]

That's easy.

[Kaitlin Olson]

All good. That's an easy one.

[Chelsea Handler]

Problem solved, guys. That was easy.

[Kaitlin Olson]

You're welcome.

[Kathryn Law]

All right, Nicole. Good luck, baby dust. Our next question comes from Redneck Kitty. She says, dear Chelsea, my name is Rachel, but my DJ, producer, entertainer name is Redneck Kitty. I'm 31 and I started DJing when I was living in Australia at the start of COVID I was a Covid dj. It's a thing. I'm single with no kids. Nine years ago, I lost my brother and partner and that cracked me open in a very YOLO way of living. I traveled the world, stripped to fund my dive trip and went on skiing and climbing adventures, Went from mansions to dumpster diving and had all sorts of wild adventures in between.

[Chelsea Handler]

Wow.

[Kathryn Law]

Therapy eventually reminded me that I might live longer than tomorrow. So maybe I should plan a future after being at my soul's end with stripping. Last year, I was messaging ChatGPT about switching careers, but decided first to consult mother Aya. And she was very clear. Music is my path. So I gave up stripping after nine years to pursue music. Luckily, I've saved smartly. And along the way, I met a couple sugar daddies who believed in me enough to give me some cushion to focus on my art. Now I've moved across the country to study under a legend in the electronic music industry. I'm in school and I love what I'm learning. But here's the problem. There's still this gremlin in my head screaming, who are you at 31 to suddenly decide you want to be a DJ? You're too old. It's a stupid choice. You'll never make it. You'll be a broke, struggling artist forever. I should have started 10 years ago. Pursuing art feels scarier than free climbing a cliff without ropes. And I'm terrified. So here's my question. How do you draw from that deep well of self belief and confidence? How do you drown out the gremlins when your heart knows what it wants, but your head just wants certainty? Is this a stupid idea? How do you trust yourself when your path isn't normal? Any advice on pushing past the fear and owning my space would mean the world. Redneck Kitty.

[Chelsea Handler]

Hi, Redneck Kitty. How are you?

[Redneck Kitty]

Hi, I'm good. I'm actually just like, so Excited right now.

[Chelsea Handler]

This is our special guest today. Caitlin Olson is here.

[Kaitlin Olson]

Hi.

[Chelsea Handler]

Hi, Caitlin.

[Redneck Kitty]

Nice to meet you.

[Kaitlin Olson]

You too.

[Chelsea Handler]

Oh, I love your story. What a nice, adventurous life you've lived. And you're only 30. You have a whole. You have two thirds of your life left to go. And by the way, maybe more than that, because they say if we make it through the next 10 to 15 years, you can extend your life to. Until you're 150. I don't know who the fuck wants.

[Redneck Kitty]

To do that, but maybe it'll tap out before then.

[Chelsea Handler]

Yeah, I know. I mean, who could afford to do that? I think. Listen, we all have those voices in our head, right, Caitlin? I mean, we all kind of don't know what we're doing or not certain of what we're doing. The proof that you have is that you're here and you got the choice to do what you wanted to do, and you got yourself all this way so far. You're 31 years old. You're not too old for anything. This is the beginning of a new adventure. You've got yourself in a situation where you can actually choose what you want to do. That is so powerful.

[Redneck Kitty]

I think it's just like. I don't know, I kind of get in, like, the comparison space, which I know is, like, comparison is a thief of joy, but, like, I compare myself to all these, like, musical prodigies who, like, started when they're 18 and I'm. Or even you, like, you know, you kind of, like, knew since you came out of the womb that you were, like, destined for greatness. Like, you were like, I'm above all of you guys, you know? And I was like. I kind of like a late bloomer in this of, like, I don't know, realizing my path. And so I kind of, like, get in my head about it because I didn't know sooner that it's not right. And I. I don't know, that's just kind of like, what I get in my head about. And, like, you talk a lot about wanting women to know they have, like, this deep well of resilience and strength and confidence that they can call on, and I'm just, like, curious, maybe, like, more practical tips on how you actually do that.

[Kaitlin Olson]

But don't you, when you look back on your life, go, oh, my God, look at everything that I have accomplished and lived through, and here I am. And everything took you one step closer to where you are right now. And I think that you. I get that feeling at 31, felt really old to me, too. I started doing Sunny when I was 29. And, like. And then I always say my 30s were way better than my 20s, which I thought was gonna be impossible. And then my 40s were way better than my 30s. You're just getting started. And I think practically, when you look back and you go look at everything I've survived, I'm sure you've been through a lot more than what you have written out in your email. So you rely on that stuff, and you go, look at me now. And you also, you're so charismatic and beautiful, and what do you have to lose? You know?

[Redneck Kitty]

Yeah. Thank you. That's really nice.

[Chelsea Handler]

Yeah. And also, you know, off of what Caitlin just said, a great exercise. And this is in that book David Hawkins wrote that I always talk. Letting go is writing down all of the things that you have accomplished. Writing down where you came from, what you went through, how you, you know, all of the things you listed in that letter alone. I'm sure there's a zillion other things, but writing down as a reminder. And every once in a while, like, when I read that book, I'm reminded to do that, like, all of the milestones I've reached, all of the accomplishments that I've had. Even if you just go back a year and think about the biggest moments that you've had in the last year, as a reminder of your tenacity and as a reminder to yourself of how powerful you are, you're choosing to make a decision. You're not letting life happen to you. You're happening. You know what I mean? You're making your life happen for you, and there's a lot of power in that. And there's so many people who call into this podcast who don't have half of the confidence that you have and who haven't made those choices or haven't had the strength of mind to make determinations about what they want to do in their future. And you're already doing that. So, like, I would say when you get off of this call, to literally just write down everything you've accomplished in the past year, and then you're gonna see it in writing and you're gonna understand how far you've come. And if you could do that every few months and as a reminder and, like, set it in your calendar and your phone as a reminder to really reflect. Because this is the problem that I find is that we go so fast sometimes, and Caitlyn's life is just as busy as anybody's. Like, you forget you know, you forget to sit there and actually take a moment and be like, wow, you just got through all of this stuff, and you just did this, and you did this and you did. You know, I made this decision, and I made this decision. I got out of that relationship. I'm into this. Like, all of the things that make you a person are really important to constantly think about instead of just zipping through life with no time to enjoy what you've done.

[Redneck Kitty]

No, you're so right. Like, even just hearing you talk about it, like, when I moved to Australia, I had, like, 500 in my pocket, and now here I am even just saying that, I'm like, yeah, damn. Yeah, I have done done it. Yeah, that's cool.

[Chelsea Handler]

So hang up from here and do that, will you?

[Kaitlin Olson]

I will.

[Redneck Kitty]

I'm gonna make my list.

[Chelsea Handler]

Okay, great, great. And then put it on your refrigerator and kiss it every morning.

[Kaitlin Olson]

Yes. In a mirror.

[Redneck Kitty]

Different color lipsticks.

[Chelsea Handler]

Yeah, exactly. That's right.

[Redneck Kitty]

That's the spirit.

[Chelsea Handler]

That's the spirit.

[Kathryn Law]

And then also, if you have, like, a SoundCloud or something, send me the link and we'll put it in the description so people can check you out.

[Kaitlin Olson]

Oh, nice.

[Chelsea Handler]

Yes.

[Redneck Kitty]

I have a new EP coming out. Bootylicious Bootlegs. It's basically a bunch of remixes to, like, the Crunk, Dirty south hip hop. I was raised on made into, like, tech house, so if you're into that kind of stuff. Yeah, I'm excited. It's my first songs I've made. I made a song. I'm so excited. There you go.

[Chelsea Handler]

You made a song that's number one on your list. I made a song.

[Kaitlin Olson]

I can't.

[Chelsea Handler]

I can't believe it.

[Kaitlin Olson]

I know.

[Redneck Kitty]

This podcast is amazing. I feel like I'm having a moment. Like, my best friend, she saw you in Vegas, and she had, like, a moment where she, like, touched her hand and had a full anxiety spiral for three days that I had to talk her out of because she was like. I felt like I met God.

[Chelsea Handler]

Oh, my God. Oh, poor thing. Well, tell her I said hello, and she has not met God, and none of us ever will.

[Kaitlin Olson]

As far as I'm concerned, she's the.

[Redneck Kitty]

One who put me on this podcast, and I haven't even told her that I was going on oh, my God.

[Chelsea Handler]

And hear it.

[Redneck Kitty]

And so shout out you know who you are.

[Chelsea Handler]

I'm not going to say your name.

[Redneck Kitty]

Because she'll get pissed, but, yeah, she.

[Chelsea Handler]

Loves you so much.

[Kathryn Law]

All right, thanks so much.

[Chelsea Handler]

We'll talk to you soon.

[Kathryn Law]

Okay.

[Chelsea Handler]

Thank you guys.

[Redneck Kitty]

Have a great day.

[Kaitlin Olson]

Bye bye.

[Chelsea Handler]

Look at how healing you are. Caitlyn with this is two, two home runs back to back. I mean that's that good light energy. That's ebullience.

[Kaitlin Olson]

Exactly. We're really doing it. We are really saving everyone. I love this way to hop on.

[Chelsea Handler]

The train and get the party started.

[Kathryn Law]

So our next question comes from Jen. She says, dear Chelsea, I have a 7 year old daughter who's a spitfire. She's wonderful and loving and kind, but also she's exhausting. She challenges every single thing. When she doesn't get her way with her negotiation skills. She'll be an amazing lawyer or hostage negotiator someday. I don't spoil her. And she's very upset about that. She feels that each day after school, if it was a good day, we should go to Starbucks or Target or somewhere and get a treat. I tell her no and that we're going home. She throws a fit and whines and cries that she had a good day and she just wants a treat. I get it girl, but we can't support a Starbucks habit for the both of us. How do I help guide her to be a respectful person who listens to me and trusts me, especially as she gets into her teenage years, yet not extinguish her fire that I know will someday change the world. Jen.

[Chelsea Handler]

Well, somebody said to me the other day, I always love to ask people about their kids, like if they have favorites. I love to ask this question to men cause men always have a favorite and it changes and it moves around. But somebody said, you know, the kid that gives you the most trouble is gonna be the most successful. So that's something to hang on to. A way for your children to teach your child about responsibilities and money like is to actually break, go to Starbucks one day, go get those treats and then break down the receipt with her when you get home and show her exactly how much everything costs. I mean I got something at Starbucks the other day that was $17 and it was one thing, I don't remember what it was, but it's absolutely ridiculous. So I think just kind of getting in there early and teaching them the value of money and maybe she can do little things around the house and you have to kind of reprogram her. It sounds like just cause she had a good day, that's a reward in it of itself. You don't get a reward for a reward. You know, her having a great day is great, but that's not something to be. But also I'm not a parent. Caitlyn, do you wanna chime in here with any parental advice you might have?

[Kaitlin Olson]

Well, you should be. Cause that was perfect. And this just happened the other day. Rob took one of our kids to a doctor appointment. And so he was like, if you get up early enough, we'll go to McDonald's. I'm like, why? Why? It's a doctor appointment. You're a teenager. You go to a goddamn doctor and then you go to the dentist sometimes and then you go to the. Or like that's just, that's part of life. You don't get McDonald's every time you have to do something out of the ordinary. But because I think it's like there's no like reward for having to just deal with like life stuff. But I love what you said about come up with not basic cleanup after yourself. Cause I don't think you should pay children for cleaning up after themselves. We all live here, we're all cleaning up after ourselves. But come up with little jobs for her where she can save money. And then when she saves up enough money, she can go to Starbucks and spend it on something. I think that's great. But I totally agree with like it was a good day. So everybody fawn all over me for not. You're what in second grade? Like it should be a good day.

[Chelsea Handler]

Yeah. And also there's other ways to reward that, you know, like. Oh, like non monetary ways to go home and play. Okay, well you know, on special days, on special occasions, we'll go home and we'll play a board game together for an hour. I'm gonna give you a my sole attention and we'll do something like that together. Or we'll plan something this weekend, just you and me, and we'll do something. Like there's other ways to make it special other than, you know, going to Starbucks or to any of those places after school. And also I just think like I remember my parents financially struggling growing up and I understood about money very early that if I wanted it, I was gonna have to go get it. Like I, you know, and I was resourceful enough and this girl sounds like she's going to get to that point. I know she's only seven, right? Is that what she said? She's seven. But you really just want to impress upon her how much things cost the world we live in. And the reality, like that's something you do once a week on a Friday, you know, to celebrate the weekend. Okay, we'll go to Starbucks, you know, you know and there's no reason to do that all the time. So that's my parenting advice for today's episode.

[Kathryn Law]

All right, our next question comes from Kristin. She says, dear Chelsea, my name is Kristen and I'm 23 years old. I'm currently a mail carrier for USPS and I'm fully independent. I live by myself and fully support myself and my animals. I'm finding it hard to relate to people my age and connect with them. I live in a college town at the moment, so most of my friends are in college or fresh out, and I'm having a hard time keeping friends. I feel like I don't really relate to people my age and they're all immature and I quite frankly can't stand them. They're very self centered and weirdly mean. I'm not sure if it's me or why I'm struggling to keep female friendships. Please help Kristen, and she'll be joining us here in a moment.

[Chelsea Handler]

How old is she?

[Kathryn Law]

23.

[Chelsea Handler]

23. Hanging out with college kids that are what, 18 to 21 or like just.

[Kathryn Law]

Out of college sort of thing.

[Chelsea Handler]

Did you go to college, Caitlin?

[Kaitlin Olson]

I went to the University of Oregon.

[Chelsea Handler]

Oh, that's fun. I love Oregon. It's so pretty to live.

[Kaitlin Olson]

Yeah. I wanted to be. I wanted to be close to my parents. I really, I didn't want to leave them. It was a. A very late bloomer. Went home on the weekends.

[Chelsea Handler]

Caitlin, were you a late bloomer in other ways or in every way?

[Kaitlin Olson]

In every. I was a late bloomer in every way. I never snuck out of my house. I was like, why would you do that? My mom would be upset if she, like, if I was missing. I. All I wanted was boobs. I still kind of do, but not as much as before. Didn't have a boyfriend all through high school. Very, very late bloomer. I was like a little kid for a very long time.

[Chelsea Handler]

Got it. Hi. How are you, cutie pie?

[Kaitlin Olson]

How are you?

[Chelsea Handler]

You're so cute. Look at you on your job, sitting on your. Oh, that's okay, honey. We're all sweaty. I'm going through menopause, so I'm sweating too. So you're hanging out with younger people or people your age?

[Kristen]

Yeah, I hang out with a lot of older people. I just turned 24.

[Chelsea Handler]

Okay.

[Kristen]

And I can't seem to keep friends my age.

[Chelsea Handler]

What happens?

[Kristen]

I don't know. They ghost me. I just had a friend recently. She just un. Added me on everything and I don't know why and I don't want to Reach out because she clearly doesn't want to be talking to me. So I'm just not sure why. I connect with older women a lot better. Like 50s, 60s, I just get along with them better and it's easier to maintain relationships. But I want friends my age to like, hang out because I'm the same age as their kids and that's just not what I'm looking for.

[Chelsea Handler]

Well, okay, it's not what you're looking for, but go where the light is. Like, if you're having relationships that are respectful and like, and you're getting something out of it, it doesn't matter how old those women are. I have tons of older. I just went to dinner last night with like three 70 year old women. They're way older than me. But like, I have friends that are 20 years younger than me. I have friends that are 20 years older than me. Wherever the light is, wherever those friendships, like you're gonna make other friends in your life. This woman obviously, or this young woman that ghosted you, don't worry about her. Like, I understand that hurts your feelings. It hurts all of our feelings when we get ghosted, but just move on with like the intention of being open to friendships, whatever shape or age or size they come in. You know what I mean? Because when you have that attitude, I feel like that, that has more of like a magnetic attraction and it brings people who are more like minded into your kind of sphere. And in the meantime, hang out with these older women. That's fine. That's not gonna be the rest of your life. You're going to make other friends. You're so young, you're 24 years old. Like, like you're going to meet other people and you're gonna figure out how to maintain friendships for longer periods of time. It might not have anything to do with you, quite honestly. Is there anything you can think of that you would have done to end any of these friendships or.

[Kristen]

Well, the last one, she asked for money and I said, I can't give you money. So that's why I was like, she un added me on everything. And I thought it was because of money, but I'm like, there's no way she would unadmy just because of money.

[Chelsea Handler]

Well, I mean, that's.

[Kaitlin Olson]

Who cares? Listen, Chelsea's so right also, I think you need to just focus on what it is that you want in a friendship. And then you're gonna find that in, in good friends, it doesn't matter how old they are. And like she said, it's that this is all temporary. Who knows? Listen, girls can be really awful to each other and I like to think it's typically around like 6th, 7th, 8th grade, but it's truthfully, sadly, can be much longer than that. And that's just not something you need to be around. The second you get a weird energy or you get ghosted, then happily let that go. Just figure out what does friendship mean to you and what is it that you're looking for. And if you're finding that in older women for this small period of time, then enjoy it.

[Kristen]

I'm worried that it is something I'm doing because I continuously have these friends that I'll be with for one to two years and then randomly they just ghost me. So I'm worried I am doing something. And I've been trying to note that, but I'm not sure how to like, keep track of it.

[Chelsea Handler]

I hear what you're saying, but also, like, a friend isn't just gonna ghost you after one to two years for. I hate when, you know, when I was growing up and I had problems with, like, socially or whatever, those things don't go away. There's always people in your life that are gonna not be there permanently. But like, sometimes it really doesn't have anything to do with you. I'm not saying you're completely absolved of anything. You know, maybe you, maybe you are doing something. But also people, when, as you get older and more mature people know that you're not gonna get a hundred percent of everything you want out of every friendship, you kind of have to be willing to make mistakes or, or have people see all of you and still want to be friends with you, like that's the sign of a strong friendship. So if somebody is fickle enough to kind of ditch you after something like, you know, it is important to have self awareness and be aware of the kind of friend you are and not maybe, you know, not be too needy. I don't know if these are any of the qualities that you might recognize in yourself. Not be too needy, not be too demanding, you know, not be putting so much weight on every friendship. Just kind of go at it with a more ease. Like just think of it as more of like it's an audition. It's not permanent. You know what I mean? And just to kind of think of it in that way, like building blocks. It takes a long time to build a really solid friendship. It doesn't happen over six months. You know, that's kind of like a. Almost like love bombing. But with friendships so Just give yourself a little grace. And the women that you are friends with, ask them if there's anything odd about you or weird about you that they might recognize because they sound like real friends. Maybe they have some feedback because they know you better. But I wouldn't focus on your shortcomings. I would really focus on just your attitude towards friendship.

[Kaitlin Olson]

Yeah.

[Kathryn Law]

And even like this friend who asked for money, like, it's likely not that she's mad at you for not giving her the money. She might be, let's say, embarrassed that she asked and, you know, those sorts of things that she doesn't want the reminder. And I also just think this, like, 22 to 27 friendships are gonna be changing. You know, it's not an easy thing to go through. But some of my best friends I didn't meet until I was like in my late 20s, and they're some of my closest people. But sometimes the people you meet in your 20s, like, they're. They're kind of in and out for a couple of years. It's just. Just sort of a transient time, friendship wise.

[Kristen]

Okay.

[Kathryn Law]

Yeah.

[Kristen]

Yeah. That's just. I get told I'm weird and off putting a lot. I am very blunt and I say what I mean and I don't know, I'm not always unkind in the way I say things. So I'm worried that could be it too. I just. I feel like that's why older women get me, because it's like they say what they want, they say what they mean. They don't take anyone's bullshit. And that's how I am. That's how my mom raised me to be. And so I feel like those friendships don't last because I can be too. Like, this is what I want, this is what I don't want.

[Chelsea Handler]

Right.

[Kaitlin Olson]

Well, do you like that about yourself?

[Kristen]

I do.

[Kaitlin Olson]

Great.

[Kristen]

People think I'm way older than I am because of how I am.

[Kaitlin Olson]

Listen, there's nothing wrong with being upfront about what you want and blunt about what you think. You would recognize if you were being unkind, I think. Don't you?

[Kristen]

Yeah, I would. I think I'm sorry.

[Kaitlin Olson]

I think so too. And listen, don't be sorry. I think it's a dangerous game to start micromanaging and really putting such a microscope on every single thing that you're doing and trying to figure out what you're doing wrong. I think you need to just know what kind of person you want to be and seems like you're a pretty kind person who knows that you want friendships and knows that you're going to be honest about how you feel about things. There's nothing wrong with that. So I don't know. I don't think you should be scouring every move to be like, did I do something wrong? Did I do something wrong? Because that's not a way to live. Just be. Figure out what your intentions are and focus on what it is that you do want. And then enjoy the friendships that you have. And then they'll just kind of keep. Keep coming.

[Kristen]

Okay.

[Kaitlin Olson]

Yeah.

[Kathryn Law]

Thank you.

[Chelsea Handler]

Don't edit your personality. Being blunt and being direct. You're gonna find your people, I promise you. Yes, you will.

[Kathryn Law]

And we like your energy.

[Chelsea Handler]

Yeah, I'm into it.

[Kristen]

Maybe we'd be friends.

[Chelsea Handler]

Yeah. You're Chelsea Handler approved.

[Kristen]

Exactly.

[Kathryn Law]

All right, Kristen, we'll talk soon.

[Chelsea Handler]

Okay?

[Kathryn Law]

Check in with us. All right.

[Kristen]

Okay, thank you. Bye.

[Chelsea Handler]

We're gonna take a break, and we'll be right back to wrap up with Caitlyn Olsen. Fleur de Mel is known as an it girl brand for luxury lingerie dresses and bodysuits with a seductive chic and elevated aesthetic. Their fabrics include real silk, refined French lace, and modern stretch materials designed to feel soft, smooth, and wearable. One of their most popular pieces is the flared corset knit dress worn publicly by Taylor Swift and recognized for its flattering waistline and versatility. From brunch to evening events, their bodysuits come in cotton, lace and fashion forward materials. The full collection is available at fleur de mal.com for the first time ever, there has been a truly beautiful medical breakthrough. One shot makes you hot, but with terrifying consequences. In the new original series, FX's the Beauty, the glamorous world of supermodels turns deadly as mysterious death. Draw in FBI agents and a shadowy billionaire who will stop at nothing to protect his empire from executive producer Ryan Murphy. FX's the Beauty premieres January 21 on FX, Hulu and Hulu on Disney plus for bundle subscribers. You know how some people meal prep their dog's food? That's not happening in my house. I can barely prep my own meals that don't involve tequila. Enter just fresh from just food for dogs in it's real food. No fillers, no preservatives. And the best part? It's shelf stable. That means it doesn't hog my fridge space, and I could travel with it like it's a Carry on cocktail. Doug thinks he's eating filet mignon. And honestly, he may as well be, because here's the thing. I would Never put ultra processed garbage in my body so why would I give that to him? His coat looks shinier, he has more energy and honestly he eats better than half the guys I've dated. And you know what? I'm fine with that. Just fresh from JustFood for Dogs is the only thing that makes sense for me. Being busy and unwilling to cook for anyone but my dogs. You can try it right now with 50% off your first [e-mail] no code needed. Convenience, fresh food, and one less thing for me to screw up. Hi guys. I have some very exciting news. I am always looking for companies to support that are ethical. And let's be honest, the phone companies we've all been stuck with are not that. You know, I travel constantly and supposedly I have international free roaming on Verizon, yet my phone bills are still 300, 400 and even $500 a month. It makes zero sense. So I switched to a company with actual ethics, Noble Mobile. And they pay you for staying off your phone. The more you unplug, the more money you save each month. And the most you'll ever pay is 50 bucks. Unlimited coverage when I need it, cash back when I don't. It was started by people I know and trust. So if you trust me and want to join my mission to stop being a phone addicted zombie, come along. Go to noblemobile.com Chelsea right now and try it for just 10 bucks. That's noblemobile.com Chelsea dump skincare companies that make billions by making us feel like getting older is a bad thing. It isn't. I'm 50 years old and guess what? I love it. I have earned this face. That's why I wanted to talk to you guys about froia Organics, a company that actually gets it. They know they're not going to magically make you look like you're 20 again. And honestly, you need acid washed jeans and crimped hair to do that anyway. And I'm not looking to look like I'm 20 again. What they will do is work with your skin to make it look and feel the healthiest for your age. They do this by using wild arctic plants that survive in some of the harshest environments on the planet. Plants like arnica and sea buckthorn are packed with antioxidants and omegas that increase collagen production while repairing the skin's natural barrier. It's like the equivalent of going vegan for your face, minus the pretension and hemp bracelets. No fillers, no bullshit, just natural ingredients that your face will love. Go and check out froyaorganics.com now and get 40% off. And we're back with the magical Kaitlin Olson, who is so good at dishing out confidence to young, young girls today. I love it.

[Kaitlin Olson]

I love these young ladies.

[Chelsea Handler]

Come on. I know we have to build them up.

[Kaitlin Olson]

I needed this.

[Chelsea Handler]

I know. I needed it, too.

[Kaitlin Olson]

I know I needed this when I was that age. Yeah.

[Chelsea Handler]

Thank you so much for coming on. Congrats on all of your success. I wish you the best. I can't wait to meet you in person one day.

[Kaitlin Olson]

I can't believe we haven't met. I love you so much. I can't wait to meet you, too. Thank you for everything you do. Very inspirational.

[Chelsea Handler]

Thank you. Take care.

[Kaitlin Olson]

Thank you.

[Chelsea Handler]

Bye Bye.

[Kaitlin Olson]

Bye guys.

[Chelsea Handler]

I just announced all my tour dates. It's called the High and Mighty Tour. 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.

[Kathryn Law]

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 Kathryn Law. And be sure to check out our merch@chelsea handler.com.

[Chelsea Handler]

Fleur de Mel is known as an It Girl brand for luxury lingerie dresses and bodysuits with a seductive, chic and elevated aesthetic. Their fabrics include real silk, refined French lace, and modern stretch materials designed to feel soft, smooth and wearable. One of their most popular pieces is the flared corset knit dress worn publicly by Taylor Swift and recognized for its flattering waistline and versatility from brunch to evening events. Their bodysuits come in cotton, lace and fashion forward materials. The full collection is available @fleur de mal.com it's time to dump skincare companies that make us feel bad about getting older. I'm 50 years old and guess what? I'm loving life. Froia Organics is completely different. They know they're not going to magically make you look 20 again. And honestly, who wants that anyway? But they do use arctic plants like arnica and sea buckthorn that hydrate, repair and protect your skin's natural barrier, giving you healthy, radiant skin at any age. No fillers, no bullshit, just natural ingredients that actually work. Visit froiaorganics.com now to get 40% off a BetterHelp ad.

[Kathryn Law]

The new year doesn't need a new you in 2026. Maybe it's not about doing more, but carrying less before rushing into resolutions. The real move is to clear space. Therapy can help you do that. BetterHelp makes it easy to get matched online with a qualified therapist who can help you see what's been heavy and what you're ready to release. You can't step into a lighter version of yourself without leaving behind what's weighing you down. Sign up and get 10% [e-mail] that's.

[Chelsea Handler]

Betterhelp.Com youm guys, I have some very exciting news about an ethical phone carrier I just switched to Forget about all these other phone companies. Forget about Verizon, forget about att, forget about T Mobile. There's this new carrier called Noble Mobile and they actually pay you to stay off your phone. You can earn real money up to 20 bucks back every month just for putting your phone away. If you're like me and you're tired of feeling controlled by your phone, social media, or just disgusted by those screen time alerts, this is the answer. Go to noblemobile.com Chelsea and try it for $10. That's noblemobile.com Chelsea this is Julian Edelman.

[Kaitlin Olson]

From Dudes on Dudes with Gronk and Jewels.

[Chelsea Handler]

Sunday mornings I've got my game day.

[Kaitlin Olson]

Ritual, coffee, lucky socks and now new Morning Uncrustable Sandwiches.

[Kathryn Law]

It's all about that 12 gram protein.

[Chelsea Handler]

Boost with the new Uncrustables Bright Eyed Berry or Up and apple flavors. Bright Eye Berries got a feisty receiver energy up an apple.

[Kathryn Law]

Your classic do it all tight end.

[Kaitlin Olson]

Soft, pillowy, packed with protein and easy.

[Chelsea Handler]

Enough for Gronk to grab from the freezer.

[Kathryn Law]

Whether you're on the couch, driving to the tailgate or heading to the locker room, New Morning Uncrustable Sandwiches are the MVP of snacks.

[Kaitlin Olson]

Your new Sunday kickoff ritual starts here with New Morning Uncrustable sandwiches packed with 12 grams of protein.

[Chelsea Handler]

This is an I Heart podcast. Guaranteed human.