Pretty Tough with Maria Sharapova: Chelsea Handler

Summary

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Pretty Tough with Maria Sharapova: Chelsea Handler

Podcast: On with Kara Swisher (Vox Media)
Date: May 25, 2026
Host: Maria Sharapova
Guest: Chelsea Handler
Special Feature: Episode presented by Kara Swisher for Memorial Day

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Episode Overview

In this engaging crossover episode, Maria Sharapova sits down with celebrated comedian, author, and TV host Chelsea Handler on "Pretty Tough." The conversation explores themes of independence, authenticity, personal evolution, relationships, and the ups and downs of forging a career on one’s own terms. Chelsea opens up about her approach to honesty, aging, the importance of laughter, her independent streak—professionally and personally—and the lessons she’s learned along the way, all with her signature humor and unfiltered candor.

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Key Discussion Points & Insights

1. Radical Honesty as a Lifestyle

• Chelsea's Truth-Telling: Chelsea explains her compulsion to be candid—sometimes to her own detriment.
  • "I have to tell the truth because I'm incapable of anything else… I don't lie a lot. I sometimes lie just to, you know, protect people's feelings." (04:43)
• The Cost of Honesty: She notes that this openness often gets her "in trouble," but she's accepted it's simply part of her personality.
  • "The truth always gets me in trouble. Like today, I'm constantly running my mouth." (05:07)

2. Growing into Herself at 50

• A New Perspective: Chelsea reflects on midlife as a period of renewal, not decline.
  • "When I turned 50, I was like, oh, this is a reset… I feel calm, rather than crazy." (06:28)
• Therapy & Growth: She discusses getting serious about therapy in her 40s and finally feeling more optimistic and happy.
  • "Now that I'm 50... I feel very more. I feel much more optimistic and happy in a way that I haven't felt in my life." (06:48)

3. Psychedelics, Control, and Personality

• Experimentation: Chelsea candidly shares her experiences with psychedelics and self-exploration.
  • "I had a little LSD... and then I gave those to my friend when I left and said, would you like the rest of these?" (08:00)
• Control vs. Letting Go: Chelsea feels comfortable being out of control, unlike Maria.
  • "You don't like it?" – Chelsea, about Maria's discomfort with losing control (08:55)

4. Independence in Life and Relationships

• Solo by Choice: Chelsea values her independence, even in relationships.
  • "I will never live with a man. Not full time." (14:02)
  • Prefers long-distance and personal space, despite having a boyfriend ("Cowboy").
• Modern Approaches to Partnership: Both reflect on the shift away from traditional views on marriage and motherhood.
  • "Marriage seems... a bit antiquated. I agree… there's not really a reason to get married anymore." (15:00)
• Advice for Women:
  • "…not to be so desperate to find your quote unquote one or the one. I think that's a load of garbage we’ve all been fed." (15:41)

5. Career Identity & Evolving Purpose

• Still a Comedian: Chelsea still identifies as a comedian, though she sees herself as a multi-hyphenate public figure.
  • "I strongly identify with the term comedian." (18:46)
• Responsibility of Bringing Joy: Chelsea embraces making people laugh as a form of healing.
  • "My responsibility as a comedian [is] to bring joy and laughter and medicine." (19:17)
• Shifting Focus: Both discuss the shift from early-career striving to a more outward, generous view of success.
  • "You’re living for yourself…then as you get older, you go, what am I giving out?" (20:10)

6. Money, Generosity, and Self-Sufficiency

• Freedom via Finances: Chelsea emphasizes making and spending her own money and being generous.
  • "I earned my own money and I like to spend my own money and I like to share money." (21:28)
  • Maria recalls Chelsea supporting her emotionally during tough public moments.

7. Navigating Social Media and Influence

• Adapting to New Media: Chelsea admits she’d be overwhelmed starting out in today’s social media landscape.
  • "Oh my God, I wouldn’t even know where the fuck to begin." (22:57)
• Being an Influencer vs. Creator: She prefers the term "creator" over "influencer," acknowledging the changing landscape of celebrity and personal brand.
  • "Creator doesn't have, to me, as negative a connotation as influencer does. I guess creator's like the new influencer, right?" (25:58)

8. Decision-Making and Work Ethic

• Work Style: Chelsea doesn't plan far in advance; inspiration drives new projects.
  • "I get a hair in my ass, and then I'm like, okay, I got something..." (28:32)
• Writing Process: Her stories start on stage and gradually make it into her books.
  • "If I'm telling a story on stage and it’s really funny…if I really want to get into that story and write about it in a book, I have to get into the details…" (31:14)
• Investment Wins & Losses: A candid confession about investing $250k in a now-bankrupt makeup brand, and her pride in backing a pro volleyball team with Maria.
  • "I invested $250,000 into nude sticks ... and then they went bankrupt." (36:12)
  • Both are investors in the same volleyball team (36:54)

9. Rapid-Fire ‘Pretty Tough’ Questions (39:23+)

• Unlearning: Chelsea had to learn not to insert herself into everyone's problems.
  • "Some people don't want help. Right." (39:36)
• Routines: Daily exercise is non-negotiable for clarity and strength.
• Misconceptions: The belief that she’s "difficult."
  • "Just that opinion about that I’m difficult. Like, I'm not difficult. I'm pretty straightforward. Like, I'm not drama." (40:54)
• Body Image: Despite her confidence, Chelsea is still working on being less critical of her body.
  • "I still don't love my relationship with my body... I just want that narrative to get out of my mind..." (41:15)
• Feeling Tough and Pretty: She feels tough standing up to men, pretty when skiing without makeup, and powerful when dressed up.
  • "Giving it to men straight… Letting a man know, like, don't come any closer and don't fuck with me." (42:24)
  • "When I have no makeup on and I'm skiing… I feel cute, natural." (42:36)
• Leadership: Chelsea prefers not to be the leader, but will step up if necessary.

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Notable Quotes & Memorable Moments

• On turning 50:
  "When I turned 50, I was like, oh, this is a reset. Like, I have my shit together now.” – Chelsea Handler (06:28)

• On independence in relationships:
  "I will never live with a man. Not full time." – Chelsea Handler (14:02)

• On societal expectations:
  "We've been sold this pile of goods that tells you, like, your value as a woman comes from being married and being a wife, being a mother, all of those things." – Chelsea Handler (17:09)

• On creativity:
  "There is a time to plant and a time to harvest..." – Chelsea Handler (28:32)

• On regretful investments:
  "I invested $250,000 into nude sticks ... and then they went bankrupt." – Chelsea Handler (36:12)

• On toughness:
  "Giving it to men straight, you know, eye to eye. Letting a man know, like, don’t come any closer and don’t fuck with me. Makes me feel pretty good." – Chelsea Handler (42:24)

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Important Segments & Timestamps

• Chelsea on honesty & getting in trouble: 04:42–06:09
• Turning 50 & personal renewal: 06:19–07:37
• Psychedelics & control: 07:56–09:04
• Relationship independence: 14:02–16:18
• Female independence & societal scripts: 14:54–17:44
• Career identity and new projects: 18:43–19:01; 28:32–30:19
• Social media, influence & adapting: 22:57–25:58
• Investment success & failures: 36:09–36:55
• Rapid-fire tough questions: 39:23–43:28

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Tone and Chemistry

The tone throughout is lively, irreverent, and intimate, reflecting the strong friendship and mutual respect between Maria and Chelsea. Chelsea’s humor, self-awareness, and candor shine, while Maria’s thoughtful questions and willingness to be self-deprecating create an open atmosphere for meaningful, occasionally vulnerable conversation.

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For Listeners: Why This Episode Stands Out

"Pretty Tough"'s conversation with Chelsea Handler offers not only laughs but thoughtful insights about navigating authenticity, aging, evolving ambition, and defining success and independence for oneself—especially as a woman in the public eye. Chelsea’s advice and anecdotes are bold, relatable, and refreshingly real.

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Transcript

[Kara Swisher]

Hi, everyone. From New York magazine and the Vox Media Podcast Network. This is on with Kara Swisher. And I'm Kara Swisher. Happy Memorial Day. We're off for the holiday, but we've still got something special for you today. We're bringing you an episode of tennis star Maria Sharapova's new podcast, Pretty Tough. It's another great Vox Media podcast that you should be listening to. In this episode, Maria sits down with one of my favorite people, comedian Chelsea Handler. They talk about how Chelsea has managed to maintain her independence over her decades long career and what keeps her going.

[Chelsea Handler]

Now.

[Kara Swisher]

Maria's interviews are as tough as her backhand. And you all know how fun Chelsea is to talk to, so stick around.

[Chelsea Handler]

You are the only person on your team that knows me, so you should be able to handle the situation. Maria, you have a podcast now and you need to start acting like it.

[Maria Sharapova]

I need to be a professional.

[Chelsea Handler]

Yeah, you're a podcast, bruh.

[Maria Sharapova]

Teach me.

[Chelsea Handler]

You're a podcast, bruh.

[Maria Sharapova]

What's the first step as a podcaster?

[Chelsea Handler]

Well, you have to ask lots of questions, which is like, annoying, I know, for you because it's a totally different situation.

[Maria Sharapova]

Well, it's annoying interviewing you because you ultimately lead the conversation. So.

[Chelsea Handler]

But that's going to be a gift for you because it's going to be easier because you're going to be able to ask me a question and then I'm going to be able to expound on it for so long that you don't even have to ask that many questions.

[Maria Sharapova]

Should I just leave then?

[Chelsea Handler]

Maybe.

[Maria Sharapova]

Okay, this is over.

[Maria Sharapova (Podcast Intro)]

My next guest and I are polar opposites. Comedian Chelsea Handler has built a career on saying exactly what's on her mind, whether it gets her in trouble or not. From stand up to best selling books and hit shows, she's never really followed anyone else's rules. She came to watch me play at the Olympics in 2012 and we've been friends ever since. What I've always found so impressive about Chelsea is her independence. She's created a life completely on her own terms and she's constantly evolving, whether that's through therapy, travel, or, yes, even psychedelics. So I had to ask her, after all the success, what keeps her pushing forward? And does she think I should try a little experimenting once in a while? As always, her answers surprised me. This was a fun one, because anytime Chelsea's around, I know I'm in for a funny, unfiltered, an incredibly thoughtful conversation. I'm Maria Sharapova, and this is pretty tough.

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[Maria Sharapova]

First of all, thank you for doing this. It means we like. This is like a testament to your loyalty, so I appreciate it.

[Chelsea Handler]

You're welcome.

[Maria Sharapova]

Yeah, I like to start these segments with a quote. And you've had a lot to say, so it was. It was really challenging pulling a quote from you. But the one that I really favored was I have to tell the truth because I'm incapable of anything else. Is that accurate? Is that a false. You said it on Fallon.

[Chelsea Handler]

Yeah, I.

[Kara Swisher]

Well, that.

[Chelsea Handler]

I wouldn't qualify that as like a quote. You know what I mean?

[Maria Sharapova]

But you said it.

[Chelsea Handler]

Well, I too, tell the truth.

[Maria Sharapova]

Mostly. Let's not argue.

[Chelsea Handler]

I don't. I don't lie a lot. I sometimes lie just to, you know, protect people's feelings. But as a general rule, especially as a woman, I believe it is very important to be truthful A with other women and B, with everyone else.

[Maria Sharapova]

And when. When was the last time the truth got you in trouble?

[Chelsea Handler]

Oh, all the time. The truth always gets me in trouble. Like today, I'm constantly running my mouth. I mean, I'm sure I'll say something in this interview that will get me into trouble or, I mean, at some point today. I have a lot of interviews today, so at some point I will say something that will be like, in the news. Chelsea Handler said this.

[Maria Sharapova]

Okay. And do you like that?

[Chelsea Handler]

No, no, I don't mean to do that. I just. It's my personality, and I've learned to accept it.

[Maria Sharapova]

And the moment you feel it, like you're. The truth is going to.

[Chelsea Handler]

Yes, just be. I just like to be candid. I don't like to be guarded. You know what I mean? Like, you're more guarded because you've grown up, like, having to protect yourself in a way. I've kind of, like, made a living out of just showing, like, being myself, rather, you know, like, having my personality out there. So I forget sometimes that things are going to be taken out of context, or sometimes they're not even taken out of context. I just shouldn't have said it. I shouldn't have been so forthcoming.

[Maria Sharapova]

I mean, most people struggle with being honest, but you don't, because it's just you. That's you. It's your personality.

[Chelsea Handler]

Yes, I think so. I think that's what I've Learned in the 50 years that I've been with myself. I've learned that. That my. That is a big chunk of my personality is to just say what's on my mind.

[Maria Sharapova]

I mean, it's really. It's really admirable that you're 50 years old and you are growing and getting better, and you're aware of it. Like, what are you still searching for?

[Chelsea Handler]

Well, I mean, you say 50, like, it's over. And I would argue that 50, now that I am 50 and I understand life more than I did when I was 30 or 40, is that you get so much more wisdom and you get so much more experience that you actually feel like you're beginning again. Like, when I turned 50, I was like, oh, this is a reset. Like, I have my shit together now.

[Maria Sharapova]

I'm recalibrating in a way that I

[Chelsea Handler]

didn't have my shit together in my 20s, 30s, or even my 40s. In my 40s, I was. I went through, like, a real rough patch in my 40s. And I think it's probably called a midlife crisis, because that's what happens when you turn that age. You start to really think about what's what are you contributing? Like, what's your purpose? Why are you here? Who are you here for? Are you making, like, people feel good? Are you making them feel bad? Like, what do you want to do with your life? So now that I'm 50 and I kind of went through all the ugly therapy part of really getting, like, into the stuff that you don't want to really talk about when you're younger, I feel, like, renewed. And I feel very more. I feel much more optimistic and happy in a way that I haven't felt in my life. Like, I feel calm rather than crazy.

[Maria Sharapova]

That worries me.

[Chelsea Handler]

So I feel like you have a lot to look forward to in all women and men. But I'm a woman, so I'll speak to that. Have a lot more to look forward to. Like, I always looked at 50. Like, oh, I'll be dead by 50. It's like, well, no, no.

[Maria Sharapova]

Because of how much you drink?

[Chelsea Handler]

Well, partly, but also because of all the other shenanigans I get up to, you know, how.

[Maria Sharapova]

How often are you microdosing and psychedelicing?

[Chelsea Handler]

I had a microdose.

[Kara Swisher]

I was.

[Chelsea Handler]

Just Came from Aspen. I was there for three days. I had a little LSD while I was there. That was the last time. And then I gave. I had about 10 little pieces of paper hits that I brought with me. And then I gave those to my friend when I left and said, would you like the rest of these? Cause they lived in Aspen. And I felt like probably now's not a good time to travel with drugs, so I'm just leaving them all over the world.

[Maria Sharapova]

I never thought we'd get to a point where we'd be talking about traveling with drugs.

[Chelsea Handler]

Yes, but here we are. That's why you invited me on this podcast.

[Maria Sharapova]

I mean, knowing what you know about me, do you suggest I try psychedelics?

[Chelsea Handler]

I don't think that you are a drug person. I don't think that.

[Maria Sharapova]

What makes you think that?

[Chelsea Handler]

Well, you're Russian, so you like alcohol. That's just in your genes. That's in your DNA.

[Maria Sharapova]

I do. I like a drink.

[Chelsea Handler]

So that's enough for you. I don't think you're very, like. I don't want to say controlling.

[Maria Sharapova]

Controlling, no.

[Chelsea Handler]

Controlling, yeah. Controlling, yeah.

[Maria Sharapova]

Now I feel it when I'm out of. When I'm not in control.

[Chelsea Handler]

You don't like it?

[Maria Sharapova]

No.

[Chelsea Handler]

Right. I don't mind being out of control because I'm always a little. Even as. As. As high as you can get me. I still know what's happening.

[Maria Sharapova]

I mean, I have a question in my notes because I was listening to a few of your podcasts and I was like, God, she seems so in control. What? Like, is there anything that throws you off?

[Chelsea Handler]

Yes, But I think my experience. First of all, I have a very strong constitution. It takes me a lot of drinks to even, like, catch a buzz or to get drunk. Like, I don't get drunk a lot.

[Maria Sharapova]

I mean, you've practiced.

[Chelsea Handler]

I've practiced since Malcolm Gladwell is, like,

[Maria Sharapova]

really proud of you.

[Chelsea Handler]

If you put in 28,000 hours or

[Maria Sharapova]

whatever it is, I thought, yeah, 28.

[Chelsea Handler]

I don't know, 10,000 hours.

[Maria Sharapova]

I thought it was just 10,000 steps.

[Chelsea Handler]

Well, that's per day. Okay, you're getting those two things confused.

[Maria Sharapova]

I am.

[Chelsea Handler]

So 10,000 hours. 10,000 hours of something makes you an expert. I'm an expert in drinking and drug use.

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[Maria Sharapova]

Hi, I'm Maria Sharapova, host of the Pretty Tough podcast. Each episode I sit down with high achieving women to discuss the pursuit of excellence without apology. This week on the show, comedian and bestselling author Chelsea Handler gifts her tips on independence and aging gracefully.

[Chelsea Handler]

I would argue that 50, now that I am 50 and I understand life more than I did when I was 30 or 40 is that you get so much more wisdom and you get so much more experience that you actually feel like you're beginning again.

[Maria Sharapova]

Check out pretty tough new episodes on Wednesdays. You can watch it on YouTube or

[Maria Sharapova (Podcast Intro)]

listen in your favorite podcast app.

[Maria Sharapova]

You generally seem in control of everything, like the situation, a conversation. When you're on stage, when you're writing a book. Is there anything that throws you off balance?

[Chelsea Handler]

I guess when I feel maybe shunned or invisible, that does throw me off balance. I think if someone, like, knows me and doesn't. Isn't interested in talking to me, that, like if I'm at a party and I'm like, oh, hey. And they're like, not interested. I'm like, oh. You know, like, I get it.

[Maria Sharapova]

So you care?

[Chelsea Handler]

I. Yeah, yeah, yeah, I care. Like, that throws me off where I'm like, oh. But then I don't. I also don't harp on it. I'm like, oh, okay.

[Maria Sharapova]

But in the moment, you're sensitive to the fact that they've moved on before. You wanted to move on.

[Chelsea Handler]

Yeah, yeah. I can read the situation and go, oh, that person doesn't like me.

[Maria Sharapova]

In your last book, you dive into the value of spending a lot of time alone. Are you still spending time alone or now that you have, like, a hot new boyfriend? That's.

[Chelsea Handler]

Yeah, he's taking up a lot of my time.

[Maria Sharapova]

Okay, Is that good or bad?

[Chelsea Handler]

It's good. But he lives in Florida, which I know you love. You spent a lot of time in Florida.

[Maria Sharapova]

I did. Not anymore.

[Chelsea Handler]

Yeah, but you did. And I'll never forget.

[Maria Sharapova]

Okay, that's passed. But now you're spending time in Florida.

[Chelsea Handler]

No, no, no, no, no. I haven't been to Florida.

[Maria Sharapova]

You refuse.

[Chelsea Handler]

I'm not big on Florida. No offense to Floridians. It's not them. It's the government situation.

[Maria Sharapova]

Yeah, yeah, okay.

[Chelsea Handler]

Political situation.

[Maria Sharapova]

But he's okay.

[Chelsea Handler]

He lives in Florida, and hopefully he will not be living there for that much longer because that's not a place

[Maria Sharapova]

that I live into or if who's.

[Chelsea Handler]

No, no, I will never live with a man. Not. Not full time.

[Maria Sharapova]

Okay.

[Chelsea Handler]

No, I'm not interested in that.

[Maria Sharapova]

Even if you're deeply in love?

[Chelsea Handler]

Yeah, if we're deeply in love. You know, like, I like long distance and I like space. So when I'm working, like, I'm here in New York working for the next couple days, I want to be alone. I don't want somebody, you know, a plus one around.

[Maria Sharapova]

Yeah. I mean, you're very independent.

[Chelsea Handler]

Yeah.

[Maria Sharapova]

Yeah. So aside from making your own money, what are the ways that other women can be more independent? Maybe not to your extreme.

[Chelsea Handler]

No, no. Right. I'm not a. Yes, I understand that. I think that a one. One way to. Well, a. Yeah, you should be trying to make your own money, definitely. But also, I think women's outlook towards men has shifted in, like, the last 10 years, at least from what I can tell, where there are many women that, like, are thinking about not being married. You're not married?

[Maria Sharapova]

No, they're.

[Chelsea Handler]

And you have a baby.

[Maria Sharapova]

So I feel like that's beyond. That's. That's marriage plus.

[Chelsea Handler]

Yeah. Okay, great. Exactly. So there's a lot of women that are thinking, like, what you're thinking. And also marriage seems a lot, like, a bit antiquated, and I agree with that. I feel like there's not really a reason to get married anymore, really. You know what I mean?

[Maria Sharapova]

Like, it's just for a big fat party.

[Chelsea Handler]

Yeah. And that's like, I find. I find the need or the. I deal with this a lot on my podcast where people call in for advice. Right. Oh, no.

[Maria Sharapova]

I listened to it. I was like, she's like. She's a sex therapist. A relationship. She's just. She's become a therapist.

[Chelsea Handler]

Yeah, basically.

[Maria Sharapova]

Yeah.

[Chelsea Handler]

Yeah. I took all the things that I learned and gleaned from therapy and then just wanted to spit them right back out.

[Maria Sharapova]

It's really entertaining.

[Chelsea Handler]

I know. Thank you. I like it.

[Maria Sharapova]

It seems like you're enjoying it. Gets deep.

[Chelsea Handler]

It gets quite serious. Yeah. Sometimes I didn't intend for that to happen, so I'm like, but, you know, if somebody really needs help, I want to help them. But I think my advice to women would be, like, to not be so desperate to find your quote unquote one or the one. I think that's a load of garbage that we've all been Fed. And this is coming from someone who's very interested in the relationship that I'm in right now, although I don't look at it attached to the outcome of the relationship. Like, he's here today. He could be gone next week.

[Maria Sharapova]

Does he have kids?

[Chelsea Handler]

No. And I won't be having kids with anyone.

[Maria Sharapova]

Right.

[Chelsea Handler]

So if he does want kids, he's gonna have to do that with his next.

[Maria Sharapova]

I mean, you've made that very clear

[Chelsea Handler]

for a long time. I mean, if he's. Any questions about that, he could just refer to my Instagram.

[Maria Sharapova]

Yeah. Or one of your books. But does he have a name?

[Chelsea Handler]

Cowboy is his name.

[Maria Sharapova]

Okay. That's all you're gonna give me?

[Chelsea Handler]

Yeah. I mean, I'll tell you, but he doesn't need his name out there. I'd like to maintain some sort of privacy for him, you know what I mean? Just since. Since I've been around the block a couple times and realize how I can just destroy people's lives, you know, by dating them, that all of a sudden they're out there. It's a fair point in the public eye. It's not really fair.

[Maria Sharapova]

No, I just.

[Chelsea Handler]

That would be. My big advice, is to stop thinking about, like, that.

[Maria Sharapova]

The urgency. But I think the urgency of meeting a man comes from wanting to have

[Chelsea Handler]

children sometimes, but sometimes it's just about, like, finding the one and not necessarily even taking into account what comes after that. You know what I mean? It's like people want to be. Be in love so badly.

[Maria Sharapova]

Right.

[Chelsea Handler]

And I think that that's.

[Maria Sharapova]

They want the idea of being in love.

[Chelsea Handler]

Yeah. And we've been sold this pile of goods that tells you, like, your value as a woman comes from being married and being a wife, being a mother, all of those things. So I would implore women to really just think about what it is you want individually and then go from there instead of thinking that that's what you're supposed to do because society tells you you're supposed to do it. You can have a full life. I mean, obviously my life is specific and unique, but you could have a very full life if you decide not to have a child without, you know, without all that stuff and being a single woman.

[Maria Sharapova]

Like, no one shares those stories.

[Chelsea Handler]

Yes. Yeah. Right.

[Maria Sharapova]

I just. I want to take a second to acknowledge your posture. It's really good.

[Chelsea Handler]

Is it?

[Maria Sharapova]

Yeah.

[Chelsea Handler]

Wow.

[Maria Sharapova]

Thank you. It seems better than mine.

[Chelsea Handler]

Really?

[Maria Sharapova]

Yeah.

[Chelsea Handler]

Well, you're so tall. You're probably always over, Right?

[Maria Sharapova]

Yeah. I don't want to see any.

[Chelsea Handler]

I have to because My boobies are so big that I have to make sure that I'm not.

[Maria Sharapova]

That they stick out.

[Chelsea Handler]

Yeah, that they stick out. So people know that I'm coming.

[Maria Sharapova]

But now that you have a man, you don't need to do that anymore.

[Chelsea Handler]

Thank you.

[Maria Sharapova]

Or you need to do it more. I don't know. Yeah. Let's. Can we talk about your career?

[Chelsea Handler]

Yeah.

[Maria Sharapova]

Do you still consider yourself a comedian? Like, first and foremost. And I asked that as, like, from a point of view of, like, an identity is when I used to, like, being an athlete was a huge part of my identity, and it only had a certain limit. But the qualities, like the things that I learned in my experience through being an athlete is just continues to run through my life. Like, even when I. Even when I fill out forms and they say, what's your occupation? Even though I don't know what the hell my occupation is at the moment. I still write athlete, but now it's podcaster. Well, whatever.

[Chelsea Handler]

Athlete slash podcaster.

[Maria Sharapova]

What would you write?

[Chelsea Handler]

That's a great. I. I think that every time I'm asked that, and I just settle. I've settled on comedian, because it's like, when am I going to write author? You know? Like, I. I have thought about that, but I don't identify. Yeah, I guess I. I strongly identify with the term comedian.

[Maria Sharapova]

And you're proud of it?

[Chelsea Handler]

Yeah, yeah, I'm proud of it. I mean, I think of myself as more like, I feel like a public figure. Do you know what I mean? Like, I. But that's how I feel like. I feel like it's not one thing or another. I just feel like I'm out there.

[Maria Sharapova]

What do you feel is your responsibility

[Chelsea Handler]

as a comedian to bring joy and laughter in medicine?

[Maria Sharapova]

Because people need more so now than ever.

[Chelsea Handler]

Yeah. I want people to be happy and to remember, like, kindness, the kindness of strangers, to double down on, like, joyfulness and laughter. Like, laughter is really so important and healing and for being able to be, like, a perpetrator of that, to be able to get on stage and make people forget about how crazy the world is for an hour makes me feel very purposeful.

[Maria Sharapova]

Yeah. And I think maybe a few years back it was, like, purely entertainment, but now there's, like, a deeper when we get a chance to go and enjoy someone's performance and feel like it impacts our view or like, if when I was competing and someone's had a really crab day and they watch me have a really crab day on the court, but I figure it out and I win, like, to have that impact. I feel like it's not just a moment, It's a feeling.

[Chelsea Handler]

It is. It's a feeling. And it's like, you find. I guess, you know, for me, I think over the course of our lives, our purpose changes quite often. I mean, we're talking about it right now with you, right? Like, your purpose changes. Like, you're living, I think, for our youth a lot. We're living for ourselves. Like, what can I do? What do I want? What can I get? What. What am I? You know, what? And then I think as you kind of get older, you're like, what am I giving out? What am I? It's not just take, take, take. It's like, okay, let me share.

[Maria Sharapova]

It's hard to acknowledge that in your 20s, 30s, I think that develops over

[Chelsea Handler]

time because you're trying to identify who you are. So then you find your identity and then you, like, burrow into that, right?

[Maria Sharapova]

And you want to feed it and

[Chelsea Handler]

you want to be as successful as possible.

[Maria Sharapova]

Right?

[Chelsea Handler]

And then sometimes.

[Maria Sharapova]

And then you have successful and you're like, well, what is it?

[Chelsea Handler]

Yeah, what is this? And then you're like, is this enough? Is this good enough? Is this enough of a contribution? And then you kind of recognize the selfishness in which you've led your life. Or for me, anyway, that's how I felt. Like, oh, I'm. I'm pretty selfish, you know, like, what, I just need another big house? Or like, what do I need more money? Like what? You know, and so that. Then you start to kind of self

[Maria Sharapova]

examine, what's your relationship to money? Like, how do you.

[Chelsea Handler]

I like it.

[Maria Sharapova]

Yeah. I mean, you've always liked it from a young age. Like, you flew first class since you were. Yeah, I mean, you earned it.

[Chelsea Handler]

Yeah, I earned my own money and I like to spend my own money and I like to share money.

[Maria Sharapova]

You do?

[Chelsea Handler]

I'm very generous and I.

[Maria Sharapova]

You're a generous tipper.

[Chelsea Handler]

Thank you. Always.

[Maria Sharapova]

You're always. You're also very generous emotionally. Like, I remember. Yeah. No, I. At the time, like, when I was really struggling in my career and I had a tough moment and I had the suspension, you called me every single day and you checked in on me and you were like this. Wrote this bad piece about you, but then There was like 10 others that were really positive. So I think today we're doing okay to have someone check in. So you're. You give.

[Chelsea Handler]

That's nice.

[Maria Sharapova]

Thank you. No, it's true. It's. It's when anyone speaks about you and because they always, like, people always see talent and, you know, famous figures in a light that they want to. They have an idea, and that's what they associate with that idea. And I'm sure when I say, oh, I'm interviewing Chelsea Handler, like, something comes up, right? And whether it's positive or negative, like, they already have an opinion, whether it's about me, whether it's about you. But the first thing I say is how generous you are.

[Chelsea Handler]

Oh, that's so nice. Thank you.

[Maria Sharapova]

No, it's true. You've come up in a very different media era, very different to how it is now. Like, with social media, if you were building. If you were starting to build your career today, how would you do it differently?

[Chelsea Handler]

Oh, my God, I wouldn't even know where the fuck to begin. I wouldn't know how to do any of this because I've lived through, like. And I mean, you two, even though you're younger than me, like, we've lived. I lived. I got my first phone. Like, the Internet came out when I was, like, 19 years old, so I have my original email address. Like, I have an AOL account.

[Maria Sharapova]

So what was your password?

[Chelsea Handler]

0253.

[Maria Sharapova]

Mine was love and peace.

[Chelsea Handler]

Well, mine still is 0253, so please don't get into my account. I've been hacked. I've lived through the technology age. Now we're dealing with AI. Like, I don't even know. It's too much of a whirlwind. I guess I would just start recording videos of myself, you know, it's probably not too much.

[Maria Sharapova]

In your underwear and bra.

[Chelsea Handler]

Yeah. And start telling jokes or telling funny stories in the way in which I am known for now. And I would just be outspoken and. And probably just do what everybody else was doing. I don't know that I would have some great, grand idea, or I might just be so overwhelmed by it that I wouldn't even talk.

[Maria Sharapova]

Do you feel like you constantly have to feed this. This algorithm? Like, just constantly providing content?

[Chelsea Handler]

Um, it's pretty natural for me to provide content, so I don't feel, like, desperate in a sense. I just feel like, oh, that's easy. Let me make it. I like these kinds of videos. These are the reason, you know, like, let's do.

[Maria Sharapova]

Are you strategic about it?

[Chelsea Handler]

I mean, I have a social media team, and I, like, kind of, like, good for you. Them handle things.

[Maria Sharapova]

I need a little bit of that.

[Chelsea Handler]

Yeah, probably. It's. I mean, because I don't want to be.

[Maria Sharapova]

So what, you have an actual calendar of, like, when you're going to post something they do.

[Chelsea Handler]

I mean, I don't have a calendar, but I mean, but like, you know, I'll be like, oh, I do this thing. Kids are not that great on my social media. So I'll film like five of those and then they'll put em out, you know, over the course of six months.

[Maria Sharapova]

What do you mean kids are not that great on your social. Like, you don't have to. I do.

[Chelsea Handler]

Like a video, like a psa. Like, hey, you could be like, you could have a life.

[Maria Sharapova]

Like, you could be a parent.

[Chelsea Handler]

Like me, I get up and I smoke a joint and I get to have a cocktail at noon and then I get to take a Xanax at 3. Kids, they're not that great, you know, like silliness like that. Okay, so I have like things like that that I do.

[Maria Sharapova]

But so you are thoughtful. So my point is like, I don't think 20 years ago you're really like curating a calendar and acknowledging who this content is for.

[Chelsea Handler]

No.

[Maria Sharapova]

Whereas now we, we know.

[Chelsea Handler]

Yeah, but you. I also have a lot of help. Like I'm not trying, you know what I mean? I don't want to make it sound like I, I'm coming up with these things.

[Maria Sharapova]

I think most people do.

[Chelsea Handler]

Yeah. I mean, most people have like a social media person and. Or a strategist or whatever just to keep you, you know, relevant and as, as pathetic as that, you know, can sound. I mean, just when I said it, I was like, oh, but that's true. That's what it is.

[Maria Sharapova]

It's true. What, what do you, when I say influencer, what do you think of like,

[Chelsea Handler]

what I think of just like someone who's selling themselves in a good way or bad way. I mean, it has a negative connotation, but it's the light. Like it's the reality of where we live or the world we live in, I should say. I mean, I would be considered an influencer if I weren't a celebrity by now. You know what I mean? So I get it.

[Maria Sharapova]

Selling author or.

[Sponsor/Ad Voice]

Or.

[Chelsea Handler]

Right.

[Maria Sharapova]

I would probably do that comedian.

[Chelsea Handler]

But it definitely does. It doesn't have a positive connotation like the word creator. Creator doesn't have to me as negative as a connotation as influencer does. I guess creator's like the new influencer, right? Is that the new, like.

[Maria Sharapova]

I think it's the vanilla version of it.

[Chelsea Handler]

I think creator sounds a little bit more profesh.

[Maria Sharapova]

Like so when you're like thinking of brand deals or investments where you have to, you know, you have these, like, lists of deliverables, and you have to act like an influencer. Are you up for that? Yeah, as long as they pay you well.

[Chelsea Handler]

Whatever I do, I have a good attitude about it. If I don't have a good attitude about it, then I don't do it. Like, if I can't get behind it and be like, okay, I'm gonna do this. I'm only gonna say something. Say yes to something that, A, I really like, or B, that I'm gonna have fun doing. So if it's just, like, for money and a paycheck, I usually don't do stuff like that.

[Maria Sharapova]

You know, I don't like, for a lot of money. Wouldn't.

[Chelsea Handler]

Well, it depends how much money and it depends what it is. Yeah, I'm not really like, you know.

[Maria Sharapova]

But it has to make sense.

[Chelsea Handler]

It does have to make sense. I definitely have done things that don't make a lot of sense.

[Maria Sharapova]

Like what?

[Chelsea Handler]

And I've regretted them. I mean, I've done things for big paychecks.

[Maria Sharapova]

Yeah.

[Chelsea Handler]

Can I name them?

[Maria Sharapova]

I mean, like a brand or a private event? What?

[Chelsea Handler]

Any of the above. Like, for instance, like, as a comedian, you get asked to do a lot of corporate events, right. And they pay you a lot of money. Casinos pay you a lot of money. More money than you make at a theater. So you can say yes to those things and get a nice, fat paycheck. Or you could be like, that's miserable. And I don't like the vibe there. Like, for me, a lot of casinos don't have the right vibe. Like, I perform at the Cosmo in Vegas.

[Maria Sharapova]

You're at the casino all the time. Why does that not make sense? Seems like such a natural connection.

[Chelsea Handler]

I have a residency at the Cosmo in Vegas. That makes sense. That's something my friends can come to.

[Maria Sharapova]

Well, you can do that, and then you can go like. And then I gamble half million dollar check and.

[Chelsea Handler]

Yeah, well, I make, you know, I like that. But, like, going to a casino in the middle of Minnesota where, you know, it's not the greatest environment and it's not fun for me, or it's not going to be, you know, like an elevated situation. No, I don't want to do that, and I don't want to have to do that.

[Maria Sharapova]

You said in your book that you're not a big planner, right? That you don't. You don't approach your career looking like five years ahead. But, like, how do you. When you think of your career, I mean, There must be a strategy. Is there?

[Chelsea Handler]

No.

[Maria Sharapova]

No.

[Chelsea Handler]

I don't plan for things. It's.

[Maria Sharapova]

It's basically, how do you plan for your next book? How do you plan for your next show?

[Chelsea Handler]

I.

[Maria Sharapova]

How does that start?

[Chelsea Handler]

It's just. It's just get. I get a hair in my ass, and then I'm like, okay, I got something. Like, I have. Like. I believe very strongly that there is, like, a time to harvest, and, like, there's a time to plant, and then there's a time to harvest. And sometimes you're just planting and. Or sometimes you're just waiting in the middle. You're not doing anything. You're just like, if I can't force myself to come up with material if I'm not inspired, usually it's sparked by me going on some crazy trip and I come back or being in a

[Maria Sharapova]

relationship and breaking up.

[Chelsea Handler]

Yeah, right. That's inspiring. Like, how do you change?

[Maria Sharapova]

Or not when you want to write

[Chelsea Handler]

about it, but it could be inspiring to other people. Like, that's what I mean to circle back to. Like, you know, one of my books was, like. It was off the back of me breaking up with Jo Koy, and I was like. I was about to. I was supposed to write a book about falling in love, and then we broke up, and I was like, I had this book deal, and I'm like, all right, forget it. I'm not writing a book about break. You know?

[Maria Sharapova]

Wait, so they paid you for this book deal, and then you started writing, and then you broke up? Mm.

[Chelsea Handler]

And then I said, okay, here I'll be.

[Maria Sharapova]

We're pivoting.

[Chelsea Handler]

I said, I'll give you the money back. Like, I'm not writing a book about being in love. We just broke up. And they said, why don't you write a book about breaking up? I said, I'm not writing a book about breaking up. That's not inspiring. So then I said, give me six months, and let me see if I have something in me. And so I took six months, and I thought, do I have something? And I started writing things. And then it turned into my last book, which had a couple of chapters about my relationship with Jo Koy. Or the breakup, I should say. But it wasn't about a breakup. It was about how to pick yourself up after a breakup. And the book was about much more than that. So I think I always just. I can't do something fraudulently. Like, I have to have feel it, and I have the luxury of being able to do that in my life where I Don't have to take money. So I know not everybody has that luxury, so I recognize that every single fucking day of my life, believe me.

[Maria Sharapova]

You're also a workaholic. Like, you don't stop.

[Chelsea Handler]

I do work a lot.

[Maria Sharapova]

Yes, you work a lot.

[Chelsea Handler]

I tour. So right now I'm here for three days, and then I have, like, three shows, then I go home, and then I work for five days, you know, Like, I have lots of shit going on.

[Maria Sharapova]

You're in it.

[Chelsea Handler]

So I like that. I don't know that I. I mean, I like the. My lifestyle, and I like to afford a certain lifestyle, so. So there's definitely that element, you know, But I'm not.

[Maria Sharapova]

Is it a pressure of maintaining that lifestyle?

[Chelsea Handler]

I mean, I definitely have grown accustomed to my lifestyle, and I would like to keep things rolling,

[Maria Sharapova]

so. So you're keeping it up?

[Chelsea Handler]

Yeah, so I'm keeping it up. But I don't dislike working. I like working. So I don't think, you know, so it's definitely. There's going to be a time where I get and be like, okay, how much do I want to continue working this hard?

[Maria Sharapova]

Yeah, you work hard.

[Chelsea Handler]

Yeah. Thank you.

[Maria Sharapova]

You write a lot. Like, what is it like when you. When you have a book deal and you know there's something that needs to be delivered? What is your process?

[Chelsea Handler]

Like, my standup and my writing, it's like they kind of go together and overlap a lot. So, like, if I'm telling a story on stage and it's really funny, and that's usually, like, the funniest parts of the story. Cause it's standup. But if I really want to, like, get into that story and write about it in a book, I have to get into the details and set the scene and talk about all the characters that are part of that story. And that is, like, a nice little avenue of exploration for me. Like, as a creative person, I like to do that. Because then you're, like, assigning. You have characters, and it's like, oh, my brother and sister were there, and let me give them lines. And then, like, what did they say? And who else was there? Like, for example, there was a story in my last book about going to the Bush compound, Kennebunkport in Maine. We were renting a house there for a month, and I. And I'm friends with the Bush sisters, and they were like, oh, I'd heard I was in the area. And so they invited us over to pickleball. Play pickleball.

[Maria Sharapova]

I know that should have been your first Sign.

[Chelsea Handler]

Well, I was not interested in going. Just on the record. I was not interested in going to Kenny Bunkport. I did not wanna be seen with George W. Bush. I didn't even wanna meet George W. Bush. They guarantee. I said to them, sissies, I will. Everyone at my house wanted to go over there. I had about 10 people with brothers, sisters, friends that were staying with me. They were like, do not take this opportunity away from us because of your political bullshit. And I'm like, listen, my back was out. I was not in the mood. I hate pickleball. I had no reason to go over there, but yet I did it for the group, right? So we get there, and Barbara Bush promised me. She said, sissy, I said, I do not want to meet your father because I do not want to disrespect your father. And I don't know that I can trust my personality in this moment. I have outbursts. And she promised me that I would not meet her father. And within five minutes of landing at their house and pickleball game starting, guess whose father I met? Hers. George W. Bush.

[Maria Sharapova]

So did you control yourself?

[Chelsea Handler]

I did. I had lots of edibles that day because I knew I was going somewhere where I did not agree with them. And I did not want to do that. I didn't want to behave badly in someone else's house. That's terrible. You know what I mean? So I had a lot of drugs. My brother said to take two edibles. My sister said take three. So I took three. That subdues my personality. And I was able to go over. What was the question again? How do. Oh, oh, oh. This is. I remember we're talking about writing. So, like, that story is full of ridiculousness. Like, my brother came over. My brother didn't even recognize him at first. So he was like, oh, my God, is that the president? We're like, yeah, you idiot. How do you not know who one of the presidents was, is? And there were a lot of funny things about that story. Sophie was with us. Our mutual friend. She was with us at that.

[Maria Sharapova]

So do you go home that evening and just start writing?

[Chelsea Handler]

No, it just marinates in my brain. And we start telling the story, and then I start repeating the story. And then I start realizing how funny it is. And people are laughing at this part and that part. And then I emphasize things, and I exaggerate little things here and there for the purpose of storytelling. And then I'm like, all right, I'm gonna put this in my. Stand up.

[Maria Sharapova]

So you're testing the material before you put it in writing.

[Chelsea Handler]

Yeah, I test it in and then by virtue of that. Thank you. By virtue of doing that, then that usually leads to me putting it in my book, like, or vice versa. Like, I'll put it in my book and be like, okay, this'll be funny for standup, but I have to make it truncated and make it much shorter. So. But most of my books, like, I mean, you know, are inspired by things that have actually happened. You know, the stories are true. They're not made up. You know, some of them are embellished or put together, like as one story. Even though they were two separate stories,

[Maria Sharapova]

some of them should be embellished. Is there. Is there something that you haven't achieved yet that you'd want to achieve?

[Chelsea Handler]

Well, I'm. I just. We just sold a show to Hulu where I will be playing a washed up reality star whose daughter comes back. She has is estranged daughter, and she comes back into her life. This woman does not want to be a mother. There's a lot of similarities between me and this woman, and it's based on the kind of culture of growing up in the time that I did with reality television, like the outset, you know, the onset of reality television and all these kind of hot messes that come along with reality television. And so I would be acting and starring in the show. I will be acting and starring in the show. So I haven't done that yet.

[Maria Sharapova]

Did you pitch the show yourself?

[Chelsea Handler]

Yeah, I did, with the writer.

[Maria Sharapova]

Did you write it?

[Chelsea Handler]

No, a writer named Zoe wrote it.

[Maria Sharapova]

So how does that work?

[Chelsea Handler]

You.

[Maria Sharapova]

You come together with a writer, you have an idea, she puts it on paper and then you sell it.

[Chelsea Handler]

Yeah, yeah, we. We basically kind of like work together for a few months, preparing the pitch, preparing the idea. Then you go out to all the networks, the platforms, and you pitch the show, and then whoever buys it, buys it.

[Maria Sharapova]

The best bidder.

[Chelsea Handler]

Yeah. Do you want to pitch a show?

[Maria Sharapova]

Not yet. Oh, okay.

[Chelsea Handler]

Well, that seems like it might be next for you.

[Maria Sharapova]

Who knows?

[Chelsea Handler]

Yeah. You're good with investments, though.

[Maria Sharapova]

I think so.

[Chelsea Handler]

I think so.

[Maria Sharapova]

You're also. No, no. You've made some bad ones.

[Chelsea Handler]

Yeah, I've made some bad investments.

[Maria Sharapova]

Can I hear of one bad one?

[Chelsea Handler]

Yeah, I invented 200. I invented. I invested $250,000 into nude sticks, the makeup brand, and then they went bankrupt.

[Maria Sharapova]

How. How soon after your investment?

[Chelsea Handler]

About seven years.

[Maria Sharapova]

Oh, well, at least it was like a slow burn.

[Chelsea Handler]

Yeah. Yeah. So that was misguided and, you know, I wouldn't have done I don't know why I did that. That wasn't really thought out. I just thought somebody asked me if I'd invest, and I was like, sure, yeah, no problem.

[Maria Sharapova]

I mean, 250 is quite a big check for something that you're not familiar with.

[Chelsea Handler]

So that's.

[Maria Sharapova]

You learned your lesson?

[Chelsea Handler]

I think so. I think I learned my lesson about that.

[Maria Sharapova]

What's been one of your best investments?

[Chelsea Handler]

I just invest. Well, it hasn't been yet. I mean, but it is already because I invested in love, Volleyball, the team.

[Maria Sharapova]

I'm an investor in the team. Oh, yeah, you are. Oh, great.

[Chelsea Handler]

Yeah.

[Maria Sharapova]

Okay.

[Chelsea Handler]

So that's a great advice.

[Maria Sharapova]

Can we go to a game together?

[Chelsea Handler]

Yeah, absolutely. I'm dying to go to a game.

[Maria Sharapova]

Okay, let's go.

[Chelsea Handler]

Yeah, we'll do that.

[Kara Swisher]

Hi, Kara. Here on my podcast, I spend a lot of time talking to people at the top of their game, but there's a whole set of stories we don't hear nearly enough about. That's why I want to tell you about a new podcast at the Vox Media Podcast network. It's called and mom, and it's hosted by WNBA star Skylar Diggins and reporter Cassidy Hubarth. The show dives into what it actually looks like for women to perform at the highest levels of their careers while also navigating motherhood. Something I know a thing or two about. Not polished, not sugarcoated, and on their own terms. It's the kind of honest, complicated conversation we need more of, especially in sports. The first episode of and mom is out now. Especially special guest Shawn Johnson. Check it out on YouTube or wherever you get your podcasts.

[Sponsor/Ad Voice]

Why is this? It's still, like, burning inside of me

[Chelsea Handler]

that I feel like I am missing something.

[Sponsor/Ad Voice]

I prayed so hard for my girl. I prayed, like, every night.

[Chelsea Handler]

Prayed, prayed, prayed.

[Sponsor/Ad Voice]

And when I lost my babies, it was so hard.

[Chelsea Handler]

So that when I had them, I

[Sponsor/Ad Voice]

thought that was going to be the thing.

[Chelsea Handler]

Like, I am finally getting the thing

[Sponsor/Ad Voice]

that I prayed for, and it's going to fulfill me. And this is everything I want and more. And it was.

[Chelsea Handler]

But it was also something missing. I'm Ravin Arson, and this is the remix from Project Swagger. This series is about defining our own versions of motherhood. I am bringing in a mama I adore and admire.

[Maria Sharapova]

Meyer, my friend, fellow peloton instructor Kirsten Ferguson.

[Chelsea Handler]

Listen now at Project Swagger.

[Sponsor/Ad Voice]

Where exactly do US China relations stand? The Chinese side came in feeling as if they had figured out how to work both with and against Trump. He was inclined to try to create Moments of crisis. And then if they stood up to him, they were almost uniquely capable of making him back down. I'm Preet Bharara, and this week, Evan Osnos of the New Yorker joins me to discuss the Trump Xi Summit, which he reported on from Beijing. The episode is out now. Search and follow. Stay tuned with Preet. Wherever you get your podcasts.

[Maria Sharapova]

I only have a few questions left. Actually, these are five pretty tough questions.

[Chelsea Handler]

Oh, okay. Are you gonna ask me to spell something? Cause I'm ready.

[Maria Sharapova]

No, I'm not gonna ask you. No. What is something you've had to unlearn?

[Chelsea Handler]

To not insert myself into everyone's problems and try to help everybody. Some people don't want help. Right.

[Maria Sharapova]

And you're not Mother Teresa, and I'm not Mother Teresa. Definitely not.

[Chelsea Handler]

So stop it and let people ask for help if they want it accurate.

[Maria Sharapova]

What's a routine that's helped shape your success? What?

[Chelsea Handler]

Working out every day when I wake up.

[Maria Sharapova]

It's funny, so many women have that same answer, because it just makes you

[Chelsea Handler]

feel strong and, like, the frame of mind, clarity of mind, like, sweating in the morning is the best thing you can do.

[Maria Sharapova]

So true.

[Chelsea Handler]

And it sounds, you know, kind of, like, obvious, but it's just a great way to start your day. I like this because if you don't

[Maria Sharapova]

accomplish anything else, at least you did

[Chelsea Handler]

something I like to. I like to do that I love. Yeah. I've actually really grown to love working out, which is a sentence I never thought I would say.

[Maria Sharapova]

I know. I see your workouts. You're like.

[Chelsea Handler]

Yeah. Hardcore.

[Maria Sharapova]

Yeah.

[Chelsea Handler]

Yeah.

[Maria Sharapova]

I think you're, like, stronger than I am.

[Chelsea Handler]

I bet I am. I bet I could beat the shit.

[Maria Sharapova]

You're a better skier. You're. You're better. You're stronger. What's a common misconception about you?

[Chelsea Handler]

I mean, who knows? You tell me. You tell me. I would. You would know more about misconceptions than I would know about myself.

[Maria Sharapova]

No, but what's one that you've heard because you like to like you. You're not afraid of reading other people's.

[Chelsea Handler]

Just that opinion about that I'm difficult. Like, I'm not difficult. I'm pretty straightforward. Like, I'm not drama. I don't have any drama. I mean, I do. You know, there's drama in all of our lives, but I'm not. I'm not difficult. I don't. I'm not trying to, like, play games or be cagey, you know?

[Maria Sharapova]

No, you're definitely not. What is your relationship to Perfection.

[Chelsea Handler]

I'm not a perfectionist. I'm pretty. Like, I'm pretty. I. I still don't love my relationship with my body. I still am very judgmental about my body, even now. Yeah, I love my body. I love what? Like, I like the way I look. I'm glad that I put so much effort into it. But I still am very aware. Aware of. Oh, if I feel like I haven't worked out in a couple days or I feel bloated, like, I just want that narrative to get out of my mind. Because I would never want any woman I know to feel that way. So I could get better on that.

[Maria Sharapova]

How are you going to get better?

[Chelsea Handler]

My body image. I don't know. I just have to keep trying. And one day you get there.

[Maria Sharapova]

Okay.

[Chelsea Handler]

How's your body image?

[Maria Sharapova]

Not as good as it was when I was playing.

[Kara Swisher]

Really?

[Maria Sharapova]

Yeah. Oh, well, because I was, like, strong.

[Chelsea Handler]

Right. And you don't feel strong?

[Maria Sharapova]

Not as strong as I did, no.

[Chelsea Handler]

Yeah.

[Maria Sharapova]

Not physically, I guess.

[Chelsea Handler]

Women. I've also had a kid. Yeah, right.

[Maria Sharapova]

It's just like your body, no matter what you do, your body is never the same.

[Chelsea Handler]

Oh, yeah. Yeah.

[Maria Sharapova]

I know. You don't know that.

[Chelsea Handler]

I don't know.

[Maria Sharapova]

Okay. What makes you feel tough?

[Chelsea Handler]

Giving it to men straight, you know, eye to eye. Yeah. Letting a man know, like, don't come any closer and don't fuck with me. Makes me feel pretty good.

[Maria Sharapova]

What makes you feel pretty?

[Chelsea Handler]

When I have no makeup on and I'm skiing, you know, then I feel cute, natural. Like, I feel cute when I'm, like, not dolled up and stuff. Like, when I get dolled up, I start to feel powerful. I put on my heels professional. Okay. You have to be in the control seat. You're the driver. Like, I really like not being the driver. Like, I was saying this to my friend the other day. Like, I will always lead in a situation that requires a leader, but I'd rather not be the leader. I'd rather somebody more capable. But if there is no one more capable, then I'm totally down to do it. But I'd rather not do it.

[Maria Sharapova]

But. Which happens most of the time.

[Chelsea Handler]

But I'd rather not lead because you can't help yourself. I know, I know, but I just. I feel like it's just more efficient sometimes, you know, to get myself in there and start steering the ship. I just feel like, let's go. Come on.

[Maria Sharapova]

This is all I have for you. This was okay. Okay. We did all right.

[Chelsea Handler]

This was successful. Okay.

[Maria Sharapova]

This was very nice.

[Chelsea Handler]

Goodbye.

[Maria Sharapova]

Bye.

[Kara Swisher]

Thanks for listening to this special episode of Pretty Tough. Happy Memorial Day. We'll be back with a new episode of on with Kara Swisher on Thursday.