Kylie & Chelsea Handler on Embarrassing Vegas Nights, Flip-Flop Aversions & Bikini Skiing | Ep. 12

Summary

Podcast Summary: Not Gonna Lie with Kylie Kelce – Episode 12: "Kylie on Embarrassing Vegas Nights, Flip-Flop Aversions & Bikini Skiing with Chelsea Handler"

Release Date: February 27, 2025

In Episode 12 of "Not Gonna Lie with Kylie Kelce," host Kylie Kelce engages in a candid and entertaining conversation with the renowned comedian and author, Chelsea Handler. This episode delves into a variety of topics, including personal anecdotes, modern parenting, authenticity, and empowering discussions about women's choices. Below is a detailed summary capturing the essence of their dialogue, enriched with notable quotes and timestamps for reference.

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1. Opening Segment: Personal Updates and Fun Topics

Kylie Kelce kicks off the episode with light-hearted stories and personal updates:

• Benny's Birthday Fiasco (00:15): Kylie shares a humorous incident where her daughter, Benny, struggled to blow out birthday candles, leading Kylie to creatively assist her.
• Philadelphia Sports Passion (03:22): Kylie expresses her unwavering support for the Philly Fanatic mascot, lauding its personality and antics.

Notable Quote:

Kylie Kelce (00:15): "When she tried to blow out her candles, she only kept blowing her bangs. I got a large piece of paper, asked her to try again, and quickly waved the piece of paper to blow out the candles."

2. Introducing Chelsea Handler: A Long-Awaited Guest

As the episode progresses, Kylie transitions to introducing her special guest, Chelsea Handler:

• Chelsea Handler's Background (12:53): Kylie highlights Chelsea's achievements as a Grammy-nominated stand-up comedian and New York Times best-selling author, setting the stage for an insightful conversation.

3. In-Depth Conversation with Chelsea Handler

a. Celebrating Milestones and Personal Stories

• Chelsea's Birthday Celebrations (14:04):

  • Topless Skiing Tradition: Chelsea shares her unique birthday tradition of skiing topless, emphasizing female empowerment and sisterhood.

  Notable Quote:

  Chelsea Handler (14:16): "This year I already filmed my birthday video. It's going to come out tomorrow on my birthday. It's the energy of female sisterhood, togetherness. Let's get this and let's stick together and be empowered by each other."

• Embarrassing Vegas Tales (38:11):

  • Hotel Room Mishap: Chelsea recounts a humorous yet embarrassing incident where she accidentally peed in her shoe during a Vegas trip.

  Notable Quote:

  Chelsea Handler (38:11): "I fell into the actual Hudson river. I felt like I was making a joke to my boyfriend at the time. I slipped, fell off the helicopter... and then Chunk jumps out after me into the Hudson River. That's true love."

b. Authorship and Influence

• Impact of Chelsea's Books (19:14):

  • "Thunder Down Under": Kylie praises Chelsea's ability to authentically address topics women often hesitate to discuss, highlighting the relatability and humor in her writing.

  Notable Quote:

  Kylie Kelce (19:14): "You can hear you saying it like, you can hear you telling the story, which is so much fun to read."

• "My Horizontal Life" Success (22:57):

  • Chelsea reflects on the unexpected international success of her candid memoir, emphasizing the importance of authenticity.

  Notable Quote:

  Chelsea Handler (22:57): "Being authentic yields success. You can't argue with someone who's really being themselves."

c. Choosing Not to Have Children: A Bold Decision

• Defending the Choice (40:53):

  • Chelsea articulates her decision to remain child-free, challenging societal expectations and advocating for personal authenticity.

  Notable Quote:

  Chelsea Handler (40:53): "If you're not cut out for motherhood, you're doing your child a favor. Your unborn child a favor. The world doesn't need any more neglected or screwed up children."

• Empowering Women (43:10):

  • Kylie commends Chelsea for being a role model, especially for women who choose paths outside traditional roles.

  Notable Quote:

  Kylie Kelce (43:10): "It's so important as women to recognize that is a valid decision, that it doesn't make you any less of a woman."

d. Personal Relationships and Lifestyle Choices

• Flip-Flop Aversions (33:02):

  • A playful exchange about flip-flops and personal style preferences between Kylie and Chelsea showcases their camaraderie and humor.

  Notable Quote:

  Chelsea Handler (34:10): "For any man I'm dating, I provide footwear for them so that they can't cross me."

e. Vegas Residency and Gambling Adventures

• Chelsea's Vegas Tales (35:28):

  • Discussing her Vegas residency, Chelsea shares amusing stories, including a flawless gambling streak at the Cosmopolitan Casino.

  Notable Quote:

  Chelsea Handler (36:04): "We have an amazing track record. I believe that I have touched the Cosmopolitan Casino and that I have given it good luck because I have not lost a penny there."

4. Conclusion: Celebrating Authenticity and Empowerment

As the conversation wraps up, Kylie expresses heartfelt appreciation for Chelsea's openness and influence:

• Mutual Respect and Inspiration (43:10): Kylie lauds Chelsea for paving the way for women to embrace authenticity and personal choices without societal pressure.

  Notable Quote:

  Kylie Kelce (43:10): "You have paved the way and have had these conversations and written the books that you've written and that you continue to not only be incredibly self-aware but always grow."

5. Final Promotions and Sign-Off

The episode concludes with Kylie promoting upcoming content related to Peppa Pig, highlighting collaborations and exclusive announcements, while seamlessly transitioning out of the main content.

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Key Takeaways:

• Authenticity Matters: Both Kylie and Chelsea emphasize the importance of being true to oneself, whether in personal choices or professional endeavors.
• Empowerment Through Choice: The discussion underscores empowering women to make choices that align with their personal happiness and fulfillment, free from societal judgments.
• Humor in Vulnerability: Sharing embarrassing stories and personal anecdotes fosters a sense of relatability and connection with the audience.

This episode serves as an inspiring testament to embracing one's true self, making bold life choices, and supporting fellow women in their journeys toward authenticity and empowerment.

Transcript

[Kylie Kelsey]

Get the Angel Reese Special at McDonald's. Now let's break it down. My favorite barbecue sauce, American cheese, crispy bacon, pickles, onions, and a sesame seed bun, of course. And don't forget the fries and the drinks. Sound good? Ba da ba ba ba.

[Ryan Reynolds]

I participate in restaurants for a limited time.

[Kylie Kelsey]

Not gonna lie. Benny's birthday was this past weekend. And when she tried to blow out her candles, she only kept blowing her bangs. She kept going. I got a large piece of paper, asked her to try again, and quickly waved the piece of paper to blow out the candles. Good news is after that happened, she said, I did it to Jason. So nailed it. Let's get this podcast started. Welcome back to Not Gonna Lie, a wave original brought to you by Peppa Pig Pig. Changes are coming. I'm your host, Kylie Kelsey, communications major Philly fanatic. Fanatic. And my husband will tell you I have some very weird eating habits. As you guys can see. I am not in my home studio today. The entire Not Gonna Lie team took a field trip to New York. Coming up on today's episode. The Academy Awards are coming up on Sunday. But I'm about to have four kids under the age of five. No, five and under. You get what I'm saying? I haven't seen an adult movie in months, potentially years. It's all kids movies. So I'm going to honor the kids movies that have taken over our lives. And after that, I'll be joined right here on this very set by someone I've admired since I was a teenager. An iconic comedian and best selling author, Chelsea Handler. That is so on brand. But before we get into all that, I want to give you guys an update on the name of the NGL fan base on More Shit Monday, I narrowed down the finalists to the outliers, the not gonna liars or ngl ers. And the real ones. And the final name is now up to all of you. You can vote right on Instagram and Twitter. Follow us Gl withkiley. I'm gonna reveal the winner on next week's show. What are the odds that we did this just to arrive back at NGL ers decent? I'd say at least 90% chance we're gonna end up back with nglors. But wouldn't that make for some cute merch? We should do it. Vote for ngl ers. I don't think we're gonna add any additions to the poll because there's few things I love more than walking into a restaurant and it being a single page because I like to not have too many choices, so I'm gonna do the same for you. Three choices. One, two, three. That's all you get. I have faith that we can pick the best one. Ngl ers. That's it. Next up, doom scroll of the week. Phillies spring training is now up and running down in Clearwater, Florida. That's right, Clearwater. The Philadelphians have taken over. And my for you page hit me with a perfect TikTok to sum up the annual transition from Eagles football to to Phillies baseball. Let's see it. Queen Emma. An outstanding outfit of Eagles merch.

[Chelsea Handler]

And.

[Kylie Kelsey]

The natural swap out. The green shoes are away. The Eagle's earrings are put on the hooks. The red, white and blue. She's back, baby. Yes. Those fightin fills. She absolutely nailed this. There is a natural progression from Eagles football season which we were lucky enough that it. It got very close to spring training, which is nice because then we don't have this terribly long gap. So thank you again to the Eagles for making this a softer transition. But now spring training is underway. It's some people's excuse to get down to Florida, hit some warm weather, get some sun before the Jersey shore really amps up. So it's a great time to really ease in into baseball. Everybody knows at this point, hopefully if you don't, the Philly Fanatic, the best mascot. It's not up for debate. I'm really sorry, Swoop, but the Philly Fanatic is the best mascot on the face of the planet. And I will die on that hill. He is handsome, funny, scruffy, and we all know that's how I like my men. He can do like a very nice bring it around town with his belly. He drives a four wheeler and most importantly, he fucks with the opposing team's dugout in a way that just brightens your day. I love him. I really like. I cannot emphasize that enough. I love him deeply. Like an embarrassing amount. And I'm okay with it. He. He did surprise me at the Late Show. I was genuinely shocked. I had no idea what was happening. And that was a. I'm not a surprise person. I don't care for surprises. But my husband nailed that. My favorite Phillies players of all time would probably have to be the team that won the World Series because we were deeply invested that whole season. It is so much fun to watch highlight clips of Ryan Howard digging the ball out because he would swing so low and just absolutely knock it out of the park. Jimmy Rollins was so much fun to watch. He was so Quick. Both fielding the ball and running the bases. Chase Utley with. We're world fucking champs. Say less. That was just a really fun team to see and the first championship parade that I got to experience. I was a junior in high school, and we came in, they did not give the school the day off, but they did give us excused absences. So we just came in, dropped our note in a box, and then literally left whenever we wanted. It was one of the strangest things I've ever experienced and as a rule follower, very difficult for me. That does it for Doom scroll of the Week. And now, with the Oscars just a few days away, it should come as no surprise to anyone here that I've seen maybe one of the films nominated for Best picture. But you know what? I have seen roughly 42 times this year alone. I'm talking in 2025. Frozen. With three, almost four little ones. I thought I'd take this time to honor the movies that dominate our life with a mini award show I'm calling the Screen Time Awards. We are not opposed to screen time in our house. I really do my best to. To limit it, but not in a strict way. I will pretend that I set a timer and I will tell them one more. And then if my task that I was trying to complete is not finished, I will say, you guys were so well behaved, I'll let you watch one more. Our girls have tablets, but they only get them on planes and very rarely in the house. And they are not allowed to touch phones. That has been a rule from the very beginning. Occasionally they will borrow someone's phone and take pictures. Why? It's really into taking selfies right now. Dad's thrilled about that one. All right, let's get into these awards. The first category is. If I put this on, will you stop crying? The nominees are Frozen. The Granch. I said it. I didn't say the Grinch. I said the Grinch. Because that's the only way Benny will request it. We have finally gotten out of that. It took us about a month after the Christmas holiday to get out of watching the Grinch, Tangled and the Little Mermaid. And the winner is, you guessed it, the Grinch. Because when the little birds ski down the snowy mountainside, she will start to. She, being venny, will start to narrate the entire movie. And when the carolers follow the Grinch, she also tells you that it's very cute. You should really experience a Benny Grinch narration. Next up, the award four. Okay, the music in this actually hits, and your Nominees are. Encanto. We don't talk about Bruno. Frozen, Moana, which has been vetoed by Ellie. So aggressively because Taka is scary. That's the Lava Monster. She's out. Won't even let me turn the movie on. And wish. And the winner is. Encanto. They actually won't let me turn it on anymore. But the songs in that are so good. Our third category is. Are you fucking kidding me, Jason? They can't watch this. There aren't even nominees for this one. The winner is. Rrr. If you haven't seen it, proceed with caution. Do not put it on while kids are in the room. The opening scene alone is enough to have me ask my husband. Are you fucking kidding me? You know what I mean? The next category is Best Picture. Played on an iPad, on a plane. Like I said, it's one of the only times they get tablets. The nominees are Finding Nemo, Alice in Wonderland, Wreck It Ralph, and Toy Story. And the winner is. Wreck It Ralph. There's always some degree when they're younger of thinking that Ralph is like dad, which we love. He's like a softy, but a strong man. I see the correlation. And now the award for. Why am I crying at this? As a 32 year old woman, you know these movies, you know, they hit you right in the feels. The nominees are the Lion King Up, Charlotte's Web, and Homeward Bound. And the winner is up, of course. Are you shitting me that you made that storyline? You want to open it like that? Poor Carl. What a guy. And now there's one more special category, and that is of course the lifetime achievement award. I know we're talking about movies today, but this TV show was also made into a movie, so it technically still counts. It's been on the air for over 20 years now. The first ever lifetime achievement award goes to. Peppa Pig. The girls love this show. They tell me about Peppa and what they did in the show and then ask immediately if they can do it. I'm here for it. I love a little imagination to wrap these awards up. Not gonna lie. These cards are all blank. All of them. They're all blank. There's not a single word written on these cards. Why is that? Because we were going with our gut. Sometimes it's best to do that. And I firmly believe we've chosen the best winners. So look at us. Go Queen Emma. Nailed it. As I just mentioned, we love us some Peppa Pig in the Kelsey House. And I'm so excited to share that Pig changes are Coming for Peppa Pig and family. That's right. Today, Hasbro revealed that Mummy Pig is pregnant. And I felt honored that Mummy Pig joined. Not gonna lie. To make the big announcement. Look at us on NGL Breaking news. You can check out Mommy Pig's pregnancy reveal on my YouTube channel right now. And for all the NGL ers who are also Peppa fans, the family's exciting expansion will be showcased in the Peppa Pig the Big announcement episode premiering on March 31st on Nickelodeon. As the new family dynamic develops, Peppa will have many opportunities to show George the ropes alongside viewers who may be adapting to changes and big feelings in their own families. Again, to hear Mommy Pig's announcement, check out my YouTube channel, GL with Kylie. You don't want to miss it. She's the hilarious Grammy nominated standup comedian, New York Times best selling author six times over, about to be seven. And she's a woman I've looked up to since I read the first page of my horizontal life as a freshman in high school. Chelsea Handler, welcome to Not Gonna Lie.

[Chelsea Handler]

Thank you, thank you. Happy to be here.

[Kylie Kelsey]

I am so excited to get to sit down and talk to you. When we first did our briefings of people that I would wanna, you were, I think, the first name we put on the list.

[Chelsea Handler]

Oh, I love that. Thank you.

[Kylie Kelsey]

I don't know if it's the close proximity of like Philadelphia, Jersey. I know you're North Jersey, but also I've read every single one of your books. Because the way that you write in sort of that short story, it just keeps you so engaged that otherwise. I don't read books.

[Chelsea Handler]

Yes. I have a lot of people that say that to me. They say they don't read. I'm the only books they've ever read. Which is concerning. Damn near which is concerning. But you know what?

[Kylie Kelsey]

I'm better for it.

[Chelsea Handler]

Yes. As long as you're reading something, it really doesn't matter what.

[Kylie Kelsey]

That's it.

[Chelsea Handler]

That's my attitude.

[Kylie Kelsey]

That's it. Before we get into anything, Happy birthday.

[Chelsea Handler]

Thank you.

[Kylie Kelsey]

Right?

[Chelsea Handler]

Yes. Yes.

[Kylie Kelsey]

You've celebrated the past five years by going skiing.

[Chelsea Handler]

Mostly topless, sometimes with tops on, but yes, a topless bikini. Sometimes I have something covering my nipples.

[Kylie Kelsey]

Sure.

[Chelsea Handler]

For, you know, decency, modesty.

[Kylie Kelsey]

Yes.

[Chelsea Handler]

For my nephews.

[Kylie Kelsey]

What was your favorite version of that so far? And are you going to recreate it this year?

[Chelsea Handler]

This year I already filmed my birthday video. It's going to come out tomorrow on my birthday. I'm just editing it right now. This would be My favorite one, because it's not just me. I got a whole bunch of women to ski in bikinis with me, and I rented a mountain to so that we could ski down and do as many takes as necessary without running from the ski patrol, which is normally how we have to do it, especially when I'm topless. But my nephews have made a request a few years back and said, can you please not be topless, like, on Instagram, because we're going into college and our friends talk about you? And I was like, that's awesome that they're still talking about me and they're in college. Like, that means me. I'm still hot. And they're like, that's not how we're seeing it. And I said, okay, fine, I can respect that. But another reason why I didn't have children, and now I'm forced to adhere to my brothers and sisters children's rules for me. Do you know what I mean?

[Kylie Kelsey]

Yeah.

[Chelsea Handler]

So they're attacking me, I feel like. But I did it this year, and at a certain point, you should put your top on, probably. So I decided. But this year, it was all a bunch of women, and we all skied together, and I was in the lead, and it was really just. The energy is exactly the kind of energy I want to demonstrate for women everywhere. And it's the energy of the book, which is like, female sisterhood, togetherness. Let's get this. And let's stick together and, you know, be empowered by each other.

[Kylie Kelsey]

One of the ones I loved was the dog in the backpack.

[Chelsea Handler]

Oh, yeah, that was a. That was a. That was a cute one. Every time I see that picture, I have these pictures on my phone that rotate. And every time Bernice comes up on my backpack, I was holding Doug, who was my new dog at the time, who was £70. And then I had Bernice, who was £30 on my back. So by the time I got done with that shoot, I had lost, like, six pounds in water weight from sweating in the snow.

[Kylie Kelsey]

Yes.

[Chelsea Handler]

Yeah.

[Kylie Kelsey]

That's outstanding.

[Chelsea Handler]

Thank you.

[Kylie Kelsey]

Well, speaking of your birthday, I love how positive you are about getting older as a woman. What is your overall excitement about turning 50?

[Chelsea Handler]

I feel like 50 is a reset. It's kind of like a rebirth, a restart, a fresh. I feel so positive about my life and the way that it's turned out that if I could talk to myself as a little girl and be like, oh, my God, it's gonna be okay. You're not gonna end up, you know, indigent or on the street or become, you know, being. I was so scared when I was waiting tables that I would end up waiting tables for my whole life. Not that there's anything wrong with that, but I wanted a different kind of life. And I was just like, oh, God, if I'm so. I'm so excited that I have this lease on life. I'm so excited that I have so many women in my life to share this kind of birthday and milestone with. And I'm so excited at my energy level. Like, I remember being young and thinking 50 was old, and now that was 40 years ago, you know, when your parents were 50. And you're like, ew. And now I'm like, it's true. You're more confident. You're sexier. I'm having the best sex of my life. So I have all of these things that are happy around me, and I'm happy. Like, I'm the happiest I've ever been in my life. So there's a lot to look forward to, ladies.

[Kylie Kelsey]

And does it not feel like as you age, you sort of even further embrace the idea of, like, fuck it? Like, it just. It's sort of like. Like, in terms of aging and the way that people always want to put, like, this stigma on that you're getting older, especially as women, and then you just sort of. Like you said, you're having the best sex of your life. Is it not just like a. Like, yeah, fudge it. I can have the best sex of my life at 50.

[Chelsea Handler]

There's a definite fuck it attitude, for sure. I mean, I think I was born with a fuck it attitude that kind of never escaped me. But I did go through a period of insecurity and, like, destabilization in my 40s where I didn't feel as positive and confident as I did. And then I did the work necessary to kind of power through that, which is therapy, which is reading a ton.

[Kylie Kelsey]

Which you talk about a lot in your new book, right?

[Chelsea Handler]

Doing a ton of work and reading a bunch of books about, you know, why you do the things you do and. And really actually wanting to become the most, you know, the best version of yourself. Like, wanting to be kinder and gentler and not losing the great parts of your personality. And so while I always had a fuck it personality, now I'm. Once I kind of got through that murky area. I'm more grounded and more stable than I ever was. I went through my 20s and 30s with this, like, kind of false confidence, you know, like, you just kind of Put on this armor. And you're like, I could do anything now. It's real. Now I'm like, no, you. You really can't touch me like I'm a tree and you can't push me over.

[Kylie Kelsey]

Yeah.

[Chelsea Handler]

So I feel like I've done the work and I get to enjoy this phase more so than the kind of bravado that I was experiencing earlier in life.

[Kylie Kelsey]

Let's back up a little bit into your books. I said in your intro, I got to know you through your first books. I, like I said, have read every single one of them. My absolute favorite chapter out of any of your books was about thunder.

[Chelsea Handler]

Thunder Down Under. That was Vegas.

[Kylie Kelsey]

I mean, just the. It just was one of those where I was like, I'm really like, you wrote this, and it is exactly what you needed it to be. Like, laugh out loud funny. I mean, and I must have read it over 10 years ago, and I still like. It resonates that. That you were writing about your life experiences, specifically writing things that women don't necessarily always feel they have the freedom to speak about, because usually it's the idea that we don't have the right to talk about it because it's not. It's classless or it's all of these other ideas that, like, men can talk about it in a locker room, but we can't talk about it openly because it's crude, I guess. Right. But to be able to read that book and to see you embracing that and being like, yeah, I fucking did. That was so refreshing and so much fun to read. And I've. I've felt that through the way that you tell stories, that it's in an unapologetic way, but in. It's so pure and authentic. And you can hear you. You saying it like, you can hear you telling the story, which is so much fun to read. Did you realize while you were writing, especially those early books, that you'd become an icon for young women and how we then have progressed forward and how we can talk about things more openly?

[Chelsea Handler]

No, I didn't. No, I didn't think that. I. I think I. I've always been really true to who I am. I've never tried to pretend or to be something that I'm not. And that's what I want for every woman. You know, that is so important to me, especially young girls and. And young boys, everyone. I want them to be who they are. And I didn't realize the power in being truthful about things that most people were shying away from when I went around and pitched that book, My Horizontal Life, no American publishing company would publish it. An English company, Bloomsbury, bought the rights to it. And then they sold it in, like, 67 countries. And so I had all this success, and eventually it became a New York Times bestseller. But I had all of this success internationally. Like, America was, like, so sanctimonious. Like, a girl talking about one night stands. I'm like, half of them didn't even come to be one night stands. I would, like, skedaddle before, you know, once I saw somebody's penis or the whole night, I'd be like, I got to get out of here. I got to find my Invisalign or something. I once told a guy I had my Invisalign in my car and, like, left him in his underwear and said, I'll be right back. He's like, you have to get it now. I'm like, yes, yes. Especially if we're gonna do what you're.

[Kylie Kelsey]

Thinking we're gonna do.

[Chelsea Handler]

Yeah. If we're gonna get intimate, I want Invisalign. So I never set out to do that. No. But I definitely feel I have felt the love over the years from so many women and about being open and about saying the thing that we're told we're not supposed to say. And I don't think there is any shame at all in women being open about their sexual experiences. Yes. Do you need to get graphic? I don. That's your choice. But we have the choice. And so the choice is up to you. You know, you can do whatever you want and you can have success. And I think being authentic, I think it's a perfect lesson to demonstrate how authenticity yields success. Because you're not going to argue with someone who's really being themselves. You can choose not to like it, but you can't argue with it. So I love that I did that when nobody really wanted to do that and everyone thought it was kind of icky. I was like, no, no, no, this is good.

[Kylie Kelsey]

Right? It settled it. It was. It hit. It was very good.

[Chelsea Handler]

Actually. I have to say something about Thunder because I do a residency in Vegas and I. At the Cosmopolitan Hotel, and they wanted some of the guys from Thunder down under to walk me out on stage on the first night. And I was like, can I see their pictures first? Because I was like, I've actually slept with one of those guys and I want to make sure it's not him, so. So luckily it wasn't. But that was a concern, and that was Just recently. I'm like, is he still fucking working there? My God, he must be like almost 50.

[Kylie Kelsey]

Anyway, now your new book, I'll have what she's having. I loved it. I had sticky noted it. I was deep in it. My favorite chapter was the letter to your nieces and nephews. Because it, in raising children right now was one of those things where I was reading your bullet points of like, hey, get your shit together, pick up after yourself. Like the people in this house aren't here to pick up after you. And to read that. I'm like, how do I issue this letter to my own children? It was basically like a letter of like respect, like be respectful. But I also love that you did it in a tactical way where you explained, like it's not about the fact that I, I didn't get to the point of yelling at them. Right. Like I decided to be a little more gentle and kind about it. And still you came at it firm. It was so good. Thank you. What led you there? Like, I know that they came and lived with you and all that, but like when you arrived at that destination, were you just like, I gotta let them know.

[Chelsea Handler]

I had been on many vacations with my family. I'm a family girl. I have a huge family. My brothers and sisters can't stop procreate. Kind of like you, you know, they just want so many babies. And so I'm like, I'm. I really take a lot of pride in being a kick ass aunt. You know, I'm the one that's gonna provide the edibles. I'm the one that's gonna provide the adventure. I'm here for you, you know, and, and so I have taken. We had been on so many family vacations and then we were on this vacation and just the boys were hiding beer bottles. You just find beer bottles everywhere. Cause they were secretly drinking from my sister in law, she's Russian and you know, so everyone's just sneaking everything. And there was stuff being hidden and just belligerent and just kind of no one making eye contact with any of the people who were coming into our house to help clean or any of the food delivery people. And I just got. Had such a, such an ick feeling, you know, leaving that vacation. I just kind of felt so A, taken advantage of and B, I knew I had a responsibility in it because I was the one taking them on these.

[Kylie Kelsey]

Sure.

[Chelsea Handler]

Taking them on these lavish vacations and paying for everything and paying for housekeepers to come and clean up after them. No wonder they didn't know how to clean their rooms because they didn't think they had to when they were with me. But seeing my sisters clean up dishes, like, seeing the kids eat and leave their plates, you know, in the living room, and then my sister's going and picking that stuff up and just seeing the whole behavior of that week. We were on Martha's Vineyard that week, and I remember just at the end of the vacation, I was in one of my. Like, I just had gotten pissed, you know, and I got quiet, and my sisters are like, oh, she's about to blow. You know, like, this is. Here we go. Here we go. It's always, like, good until Chelsea flips out. And I'm like, no, I'm not going to flip out. Like, I'm going to figure out a right. The right way to deal with this. It's not yelling and screaming. It's hard to get anything done with yelling and screaming. I didn't learn on that until I was 40. And that's. It's really nice to be able to make a point or have an argument without losing your temper. And so I just thought long and hard, and I wrote that letter and revised it and revised it, and then I sent it off, and it felt fucking awesome. They didn't love it. They did not react. You know, they weren't pleased. And it took a while, but eventually every single one of them came around. At first it was funny because people were like, that's not me. That's not me they're talking about. Everyone else did that. And I was like, no, no, it's all of you. And it's also all of you. To my siblings, I'm like, you're the reason that your children are acting this way, too. I'm taking my responsibility. But you're all responsible for your children's behavior, too. And so then they were included in the let. Like, oh, no. And. And then slowly, everyone was like, we're sorry. Like, you made a good point.

[Kylie Kelsey]

But it led to better vacations, right?

[Chelsea Handler]

Yes. It led to a lot more respect and a lot more appreciation. There's really nothing as disappointing as rude children. And not that any of them are rude, but just not considerate enough at that point. Yes. Do you know what I mean? I want to please and thank you to every person you meet. When we go out to a restaurant, look at the fucking waiter in the eye. Don't lie down at a restaurant. Get up and look at that person and order your food. Don't look at your mother. You're 14. Decide what you want to eat and then fucking say it.

[Kylie Kelsey]

Yes.

[Chelsea Handler]

So all of those things, you know, it was either that or I wrote a book called Hot Parenting Tips and then that would have been like passive aggressive, you know?

[Kylie Kelsey]

Sure. Just go straight for it.

[Chelsea Handler]

Yeah, yeah.

[Kylie Kelsey]

You don't strike me as the type of person who would try and do the passive aggressive route.

[Chelsea Handler]

No, I'm not passive aggressive.

[Kylie Kelsey]

Why invest the time in the passive aggressive route when you can just be aggressive?

[Chelsea Handler]

That's it. I like aggressive aggressive, not passive aggressive.

[Kylie Kelsey]

It's way more enjoyable.

[Chelsea Handler]

I don't have the personality for that.

[Kylie Kelsey]

There's no questions. Then you're not. There's no confusion. It is what it is. Like, this is what I'm asking of you and then you. You do it. Yeah, I like that better.

[Chelsea Handler]

Yes, absolutely.

[Kylie Kelsey]

Yeah. I'm back and interrupting your regularly scheduled programming to talk to you about more exciting programming. My family loves Peppa Pig. Like I mentioned, Pig changes are coming for Peppa Pig and family now that it's been revealed Mummy Pig is pregnant and due in June. And now that you know Mummy Pig is pregnant, I'm sure you can't help but wonder, is Peppa going to be meeting a new little brother or a little sister? I always can tell right away, but Mummy Pig did not share that with us. So we'll have to wait and see. You won't have to wait too long to find out because Walmart will be exclusively revealing the gender on April 25th at 9am Eastern time in the U.S. all new baby toys will be available only at Walmart on June 1 and nationwide in August. In the meantime, Walmart is a great place to shop for all things Peppa Pig. Your essays make it clear that you've always known you were going to be successful. One of the stories that you've told, not only in interviews, but in the book, is when you walked past first class and then you promptly fixed it and ended up in a first class seat on one of your later flights. What would you consider was your actual, like, first big break?

[Chelsea Handler]

I was on a show called Girls Behaving Badly. So that was kind of a break. I mean, it wasn't like big money, but it was. I was on TV and I was on a show that was fun and it was four other girls with me and we laughed a lot and we had a great time and I was being paid to be funny, so I loved that. And then after that, I think I had had a couple development deals where they give you like a hundred thousand dollars and they're gonna develop a TV show. And so I got a couple of those deals, but that wasn't like a huge break. That was like potentially could be something and then potentially falls apart. And then I think Chelsea Lately came around right after Girls Behaving Badly led to. Then I did my horizontal life. And then I did a show called the Chelsea Handler show on E. That was only one season. And they said, we love you. This show isn't working. We'd rather. We'd like to put you on a late night show. So Chelsea Lately. And then my second book kind of came out at the same time. And then that became the big thing that became when people started to know who I was.

[Kylie Kelsey]

And Chelsea Lately, I will say this just because I have to. There's never been a dog that I've seen that I wanted to pet more than Chunk.

[Chelsea Handler]

Oh, have you seen Doug, my new dog? He's more pettable than Chunky.

[Kylie Kelsey]

Is he? Because I grew up with shepherds, and Chunk just gave like that shepherd, like. And he would just like casually walk behind you on set. And I was like, I wanted to be there. I want. That's what I want. I want a set dog like that.

[Chelsea Handler]

Chunk was such a student, he once jumped out of a helicopter after me. I fell out of a helicopter once by accident. I was tipsy at the time.

[Kylie Kelsey]

But was it on the ground?

[Chelsea Handler]

No, it was over the Hudson river, thankfully. So I fell into the actual Hudson river. And guess what? I felt I was making a joke to my boyfriend at the time. And I stepped out of the helicopter and I made this big gesture and slipped. Fell off the helicopter in a pea coat and knee high leather boots. It was Thanksgiving weekend. I fell into the Hudson river. And I was panicking because I was like, you know, it's so cold. It was November.

[Kylie Kelsey]

Take your breath away.

[Chelsea Handler]

And I'm like. And I start swimming and paddling in this big pea coat that I had. And then my foot kicked the ground, and I realized I was only in 2ft of water, swimming like an asshole. And then I look up and Chunk jumps out of the helicopter after me into the Hudson River.

[Kylie Kelsey]

That's true love.

[Chelsea Handler]

I mean, when he did that, I was like, I'm gonna marry a dog. Like, I couldn't believe the commitment and the love. Like, it was so unbesmirched love, you know, like, so pure. I. I just. I loved that dog so much.

[Kylie Kelsey]

Yeah, you could tell. And he knew, I think.

[Chelsea Handler]

Yeah. Yeah. He was my first rescue. So he made me a mother. And I've been. And now I've had I don't know how many rescues in my life.

[Kylie Kelsey]

But that was all chow mixes, right? Yeah.

[Chelsea Handler]

I love chows.

[Kylie Kelsey]

Yeah. Yeah.

[Chelsea Handler]

They have an attitude. I like that.

[Kylie Kelsey]

I would love to get into your stand up career. In your last Netflix special, you went off on straight men who wear flip flops.

[Chelsea Handler]

I know your husband wears flip flops.

[Kylie Kelsey]

I'm married to one.

[Chelsea Handler]

Yeah, I've seen that.

[Kylie Kelsey]

Uh huh.

[Chelsea Handler]

How do you feel about them?

[Kylie Kelsey]

So I, I don't mind that. I'm just so used to it.

[Chelsea Handler]

Right.

[Kylie Kelsey]

That I.

[Chelsea Handler]

That's what happens.

[Kylie Kelsey]

Yeah. It's almost like I've been desensitized to the fact that he wears flip flops and wears them everywhere. This is not like, like so much so that when he goes somewhere with actual shoes on, people like, holy shit, he wore shoes. Which to me says we might need to reevaluate that to that degree. But we, we very much have leaned into like, he just wears flip flops.

[Chelsea Handler]

In the winter time too.

[Kylie Kelsey]

Everywhere.

[Chelsea Handler]

Wow. Wow.

[Kylie Kelsey]

It's a full commit almost to the extent where like you can almost a little bit appreciate it because you're like, you're not wavering at all.

[Chelsea Handler]

Right.

[Kylie Kelsey]

The commitment is there.

[Chelsea Handler]

That's one way to look at it.

[Kylie Kelsey]

But at the same time, at the same time, he recently got a pair of boots and he's been wearing them for the last week. And I've been like, oh my God, I haven't seen your toes. And are you okay?

[Chelsea Handler]

And do you like the boots?

[Kylie Kelsey]

They're fine.

[Chelsea Handler]

You don't care either way what he's wearing. You don't care. Yeah. You have children. We don't care.

[Kylie Kelsey]

It's also why, like, I didn't care before we had kids. I. It's why we work out well. Like, neither of us are very stylish. We leave that to the other sibling in his family. Yeah. It just.

[Chelsea Handler]

I, So I, I had a guy come and meet me over the summer in Mallorca. We were on vacation and he was coming to meet me and I told him, please don't bring flip flops. Like, I know this is a beach setting and you're, you're going to be confused, but I'll have shoes for you when you get here. So what I like to do for any man I'm dating is provide footwear for them so that they can't cross me.

[Kylie Kelsey]

What is the alternative to a flip flop in a beach setting?

[Chelsea Handler]

I don't mind a Birkenstock.

[Kylie Kelsey]

Okay.

[Chelsea Handler]

I'm not Opposed to that.

[Kylie Kelsey]

I think maybe we'll try out some Birkenstocks this summer at the Jersey Shore.

[Chelsea Handler]

Yeah, Birkenstocks are hot. They would look cute on Jason. Birkenstocks. That would be a hot look.

[Kylie Kelsey]

I'm gonna order them the minute we walk out of here and see if they don't. If they don't work out for him, because we do. We spe a lot of time at the beach, so we need an alternative.

[Chelsea Handler]

But most guys that like flip flops are opposed to Birkenstocks. I wonder if Jason would care. Does he care what's on his feet? Clearly not if he's wearing flip flops.

[Kylie Kelsey]

Right.

[Chelsea Handler]

So there we go.

[Kylie Kelsey]

You mentioned briefly your Vegas residency coming up. Are you a Vegas person?

[Chelsea Handler]

I am not a Vegas person.

[Kylie Kelsey]

Okay.

[Chelsea Handler]

But I have. I do a residency, which means I go once a month for the next two years at the Cosmo. It's at the Chelsea Theater. So I get to perform inside myself, which has always been a dream of mine.

[Kylie Kelsey]

Delightful.

[Chelsea Handler]

And I bring a group of friends and we gamble. I perform, and everyone gets to come, and we get a bunch of rooms, and then we gamble every time. I love gambling. I love gambling. It is so much fun. And I always.

[Kylie Kelsey]

What's your game of choice?

[Chelsea Handler]

Blackjack.

[Kylie Kelsey]

Okay.

[Chelsea Handler]

And so I bring everyone, I give everyone money, and I'm like, okay, this is our time here, and this is all the money we have. And so far, no one has ever walked away without more money.

[Kylie Kelsey]

Really.

[Chelsea Handler]

We have an amazing track record. I believe that I have touched the Cosmopolitan Casino and that I have given it good luck because I have not lost a penny there.

[Kylie Kelsey]

That is so interesting that you say this, because last year we went to Vegas. It was the first time I had ever been in Vegas.

[Chelsea Handler]

Oh, wow.

[Kylie Kelsey]

I 32 years old. I was 31. I almost. I. I felt like I had a long streak going that I had to keep it, but they had the super bowl there and my brother in law was playing, so we naturally had to get out there. But it's funny. We stayed at the Cosmo, and my husband left with significantly more than he started with.

[Chelsea Handler]

Wow.

[Kylie Kelsey]

And he was very excited about it. So maybe we. Yeah, we worked in on that luck that you got.

[Chelsea Handler]

Maybe. Maybe you started the luck.

[Kylie Kelsey]

No, I don't know about that.

[Chelsea Handler]

And the Cosmo is actually a fun hotel. I didn't know much about it before the casino, but the selling point was that they have the Chelsea Theater. And I was like, well, okay. I mean, this makes a lot of sense.

[Kylie Kelsey]

So they Basically walked you right into it.

[Chelsea Handler]

Yeah. Yeah. So I did it. And. Yeah. But I'm not a Vegas person. I understand. It's.

[Kylie Kelsey]

It's.

[Chelsea Handler]

It's pretty depressing in the daytime that.

[Kylie Kelsey]

You know, we were there from Tuesday to Sunday, which I found out very quickly is not what you do. No, no. You need to get in and get out.

[Chelsea Handler]

Yeah.

[Kylie Kelsey]

The number of people who I saw there, and they were like, we flew in this morning. We're leaving tonight, or we're leaving tomorrow morning. And I'm like, why am I staying for a week?

[Chelsea Handler]

Like, you're tricked me into this.

[Kylie Kelsey]

Yeah. Who tricked me into this?

[Chelsea Handler]

You're a businesswoman at a conference.

[Kylie Kelsey]

I swear, I did not see the sun for three days, and that really messed me up. I can't. I'm. I'm good.

[Chelsea Handler]

Yeah.

[Kylie Kelsey]

That was enough. Vegas.

[Chelsea Handler]

Yeah. There is something. Yes, I understand what you're saying. I'm with you on that 100%.

[Kylie Kelsey]

Yeah. Now, what is the most ridiculous thing that's ever happened to you in Vegas? Because I feel like being there a week that I lived, like, a whole life while we were there.

[Chelsea Handler]

So many things have happened in Vegas. So many embarrassing things. So many hookups, so many. Well, this is really embarrassing, but I'll tell it. I mean, why not? I once was with. This is when I was in my early 20s and I was with my girlfriend, and I got up in the middle of the night to try to use the bathroom, but I couldn't. It was so dark and black that I couldn't find it. And I was banging on the walls, trying to find a door so that I could urinate. And eventually I gave up and peed in my own shoe. That was a low point for sure. And my friend who woke up in the middle of the night because she heard my stream of urine hitting the bottom of my shoe and ricocheting out of it. I didn't know it was my shoe. I thought it was just. I was like, okay, here's a receptacle. You know, other than just peeing right straight out on the floor. And I remember in the morning, there was another girl that had hooked up with a guy, and she came back, and she's like, why is there water everywhere? And we're like, it's not water. And it was just disgusting. Just a night of just debauchery. And I thought to myself, I should never spend the night here again. You know, I blame the city. I don't blame myself. Character. You know, I don't usually pee in sneakers or Hotel rooms on the ground. But that was a low point for sure. And that hasn't happened again, you know, So I think that's a victory.

[Kylie Kelsey]

That's growth is what it is.

[Chelsea Handler]

That's maturity and growing up. And I'm sure that headline is going to be all around town, so we can all look forward to reading that together. Chelsea Handler Urinates on Vegas Hotel room.

[Kylie Kelsey]

Floor Something else that I absolutely love about you is that you're very open about the fact that you have chosen to not have kids and that you don't take shit from people about it. Like, you just own it completely unapologetically. That is the decision that you've made. And you come across so settled in that decision that it's like you don't even give people the opportunity to question it. I love that because even though I have chosen to just litter my house with children, I think that it's so important as women to recognize that that is a valid decision, that it doesn't make you any less of a woman, and that ultimately you don't need anyone else to validate the fact that you've chosen to focus on yourself and the loved ones that are already around you instead of having children for whatever reason. People choose not to. Why do you think people constantly feel the need to challenge women and also you on the fact that you've chosen not to have kids?

[Chelsea Handler]

Well, I think that. I mean, it's pretty obvious that people want women in their. Their natural role and which is an antiquated role for all women. You know, now we're coming to a place where women and I talk about this a lot in the book because it's so important to know if you have what it takes to be a mother. I don't have that. What I do have is a huge bandwidth because I don't have my own family to take care of. I don't have four or five children or even two children that I have to focus on. And what that opens me up and gives me the availability to do for other children in my life is really amazing. Like, I'm able to send kids to college that I've never met. I'm able to take my friend's kids to New York and to Hawaii and to Mallorca. I'm able to do so many things that if I had my own children, I wouldn't do. So, like, it's not. You can't speak about the benefits enough. If you're not cut out for motherhood, you're doing your child a favor. Your unborn child a favor. And you're doing the world a favor. We don't need any more neglected or screwed up children. We don't need that in this world. The world is crazy enough. So I am always excited to talk about all of the wonderful things that can be yielded when you choose to understand what your capabilities are like. I have a million capabilities. Being a mother isn't one of them. I'm a really good stepdad and I thrive in that zone. I want to spoil kids. I want to show them anything is possible. That the world is, you know, endless with, and filled with possibilities if you are really authentic and understand who you are and you get after it. You know what I mean? You have a really great work ethic. You know how to work hard and you know how to be a sister to everyone and love people up. And I think that's the biggest thing that I've learned from not having a child. It's made me even more sensitive to just being a sister to the world, you know, without sounding like corny in that sense. Like sisterhood, being a woman and being there for other women and showing up and being honest and telling the truth, all of those things are really valuable and, and I take them really seriously.

[Kylie Kelsey]

That's incredible. I cannot thank you enough for coming to sit down with me today. It is such an honor to get to talk to you. And ultimately, I have to say, not only in the way that you have been a role model for myself, but I am so happy to be raising four daughters in a world that you exist and that you have paved the way and that you have had these conversations and written the books that you've written and that you continue to not only be incredibly self aware, but always grow. Like you talk about your growth and how you're constantly trying to like, be better and all of that in conjunction with the way that you lift other women in the way that you've talked about today and in your book about that sort of sisterhood is absolutely amazing. And I cannot thank you enough for, for using your voice for that and that you've, you've done that with your life. So I really appreciate it so much.

[Chelsea Handler]

Thank you. Congratulations to you on everything because this is. It's really nice to see the success that you're having.

[Kylie Kelsey]

Thank you.

[Chelsea Handler]

It's really nice. So congratulations.

[Kylie Kelsey]

Thank you. Thank you so much again to Chelsea Handler for joining me today. Make sure you check out her book. I'll have what she's having available now. You can find even more clips from our conversation on my YouTube channel on more Shit Monday. And that's a wrap on another episode of Not Gonna Lie. I'll be back next Thursday with a brand new episode. Listen and subscribe wherever you get your podcast. Follow the show on all social media at NGL with Kylie. Not gonna Lie is a wave original brought to you by Peppa Pig Pig things are chang. No. Pig things are coming. Pig changes are coming. That's changes. They're pig changes cuz it's gonna be another piggy. Should we leave that?

[Ryan Reynolds]

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[Chelsea Handler]

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[Kylie Kelsey]

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[Chelsea Handler]

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