Off The Vine with Kaitlyn Bristowe - Chelsea Handler | 50, Fearless & Giving Zero F*s!

Episode Date: February 27, 2025

#819. Chelsea. Freaking. Handler. The legendary comedian, best-selling author, and unapologetic queen of telling it like it is joins the pod, and NOTHING is off-limits. Chelsea gets real about turning 50 (and why she finally has the body she wanted at 20), what led her to write this new book and why men have never been the center of her story. She spills on sexting a certain governor, how stacking small wins (and rejections) led to her break in comedy, and her love of… well, you’ll have to listen. Plus, her brutally honest thoughts on cancel culture, the biggest “oops” moment of her career, and why she refuses to fit into society’s mold of what a woman should be. Get a copy of Chelsea’s new book, I’ll Have What She’s Having, available now at chelseahandler.com/book. This one is hilarious, raw, and SO Chelsea. Buckle up! If you’re LOVING this podcast, please follow and leave a rating and review below! PLUS, FOLLOW OUR PODCAST INSTAGRAM HERE! Thank you to our Sponsors! Check out these deals! Audible: Go to Audible.com/Chrissypodcast or wherever you get your podcasts and start listening today. Boll & Branch: Get 15% off, plus free shipping on your first set of sheets at bollandbranch.com promo code VINE15. Nutrafol: Find out why over 4,500 healthcare professionals and stylists recommend Nutrafol for healthier hair! Nutrafol.comSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Code Vine. I'm Caitlin Bristow. Your session is now starting. And why it will be? Welcome to the... Hey everybody. Welcome to Off the Vine podcast. I'm your host, Caitlin Bristow.

Another legendary guest I got to have on the podcast today. She has been someone I've always looked up to. Somebody who inspires me, she did that on this podcast. She's hilarious. just truly the most authentic version of herself who gives zero you guessed it, it's Chelsea Handler. So you don't drink a lot of water either?

I don't. I don't like water. I find it to be a real buzzkill. You know, like, I have to doctor my water up with so many electrolytes. And then at that point, I'm like, can I just snort the electrolytes? If I'm just looking for the electrolytes, why do I even have to put them in the water?

That's a good point. Do they work if you put them in ginger ale? Because I would rather do that. I've never tried, but I will say yesterday at the airport, I went to put electrolytes in water not realizing it was fizzy water and it exploded on the counter and there's a huge line behind me and everyone was annoyed. Yeah. I have elementi, you know, those cans. Yes. So that those are carbonated. Those are good. And they're electrolytes. So it's like all of my favorite things

colliding. Like carbonated water with electrolytes. Yes. I love those. And it's so salty too and they're delicious. Yeah. Yeah. Very salty. Which is perfect because they're a sponsor on this podcast. So I'm so glad we said that. okay tell me about this book you're releasing it on your 50th birthday yes it's my gift to the world for my birthday happy birthday to all of us not just you yes yes that's what i was i was informed that it was going to be released on my 50th birthday no that's not fair they asked they gave me two dates two options and i thought i might as well just blow it out you know what i mean on my birthday 50 is such a fun one are you doing anything crazy i think so i mean i have lots of different kind of like different groups of people and parties planned throughout the year.

So I'll fold that into like my book launch. I'll do something in New York. I'll do something in L.A. I always do a ski video each year. I know I'm obsessed with your ski videos. So I'm going to do that before my birthday this year. I have like a real shoot planned for that. So that'll be a nice festive thing.

Where is your favorite place to ski? I'm going to Beaver Creek at the end of the month. Oh, you are? Yeah. Oh, fun. I'm so excited. I ski and Whistler because I have a place there. You have a place.

I lived in Vancouver for 11 years. Oh, Canadian. Yes. Right. And Whistler is one of my favorite places on earth. Yeah, me too. I love Whistler. It's like my little village life when I go there.

I have like this little, I love it. I have all my friends that are Canadian up there, my ski buddies. Yes. Do people leave you alone or are they chill or do they bother you? I mean, people generally just say hi. Yeah. No one's stalking me. Well, I disagree.

Some girl, I don't know if you saw this, but I was scrolling TikTok last night and some girl freaked out that she was at the same airport as you in Vegas. Oh. Did you hear about this? Was I at an airport? When? Were you not at an airport? I don't know.

Maybe. It doesn't sound right. Stop. I would die if she was just trying to get your attention or something because this person, like, was going, I think she has a podcast too that's like does. Yeah. What's her name? Tanna, something.

I'm losing my mind. I'm losing my mind. I'm living about to start sobbing. I have to walk outside. Hold on. Oh, my God. I literally had to come outside for like a breath of fresh air. I'm in the air.

right now. I'm dead alone in this tiny Vegas airport. And I sit down and I look up and Chelsea Hamler is like 10 feet for me. Is that jet suite? Maybe. Oh, okay. Yes. Yes. That makes sense. So she was losing her noodle and she could not bring herself to go say hi to you. And apparently you've changed her life and she's such a fan. You know what? I love when people appreciate me that much. And then also don't approach me. Like what, that's like a jackpot situation. Because I'm not a, I'm not a bitch when people approach me. I'm always, you know, very nice. And I'm always, as long as I'm not with my family sitting down at a dinner

table when someone approaches and asks me to get up to take a picture. Yes. I'm pretty you know. Approachable? Approachable. Yeah. So that's why there's not, I mean, I appreciate that attitude and reaction. Yeah. But no, there's not like, yeah, it's not like I

walk around being like, don't talk to me. Well, at airports it's so tricky because, I mean, you saw Mel Robbins was just here. I'm obsessed with her and I try so hard in airports. I'm like, let them because I just find everyone so irritating. Not seeing people who come up or what. I'm just saying people in general. Just the airport is irritating. Airport. In general. So anything on top of that is a double irritant. Exactly. So I'm always just like shaking being like let them. Like last night a guy was

literally picking his foot beside me on an airplane. Yeah. I'm really done with men and their feet on planes and also having them exposed. Why would you ever think that you could touch your foot in a public area your bare foot why would you take your foot out of your shoe it's cover keep your feet covered and who wears no socks to an airport and sandals and then takes them off to walk through security oh what about people who walk to the bathroom on a plane with their shoes off into the urine soaked bathroom floor that's waiting for them the amount of times I see that happen on a plane blows my mind I just feel like there's so many I used to do a segment on my podcast called can you not and half the time it was about airports and just the

disgusting humans who fly these days. Yeah, people are, people, I, my sister was telling me a story about someone who's sitting next to her on a plane who brought spaghetti with clams on the plane. No. Yeah, with the shells. And then, and then what? Like, and then what happens to the shells? I was once on a plane where somebody brought oysters onto the plane.

Oysters. That's like bringing hard boiled eggs and tuna. And then, yeah, hard boiled eggs, don't get me started. My, my producer on my podcast has a hard boiled egg problem. And I told her, first of all, if you're going to bring hard boiled eggs and hard-boiled eggs anywhere, you need to swallow them whole. You can't take bites out of hard-boiled eggs and then just expect the rest of the people to deal with that. Agreed. I agree. There's a lot of food out there that if people bring on planes, hard-boiled eggs should be illegal. Yeah, they are so foul,

you know? Hard-boiled eggs. It's like I wouldn't even eat that in my own kitchen if people were there. Like, I wouldn't do that. You know what? I was traumatized in the fourth grade. My mom packed hard-boiled eggs for me at school and all the kids laughed at me and wouldn't sit next to me. And I've just some traumatized by hard-boiled eggs now. Yeah, yeah. My mom used to make me cream cheese and jelly sandwiches. Pardon? I was like, it's peanut butter, you dumbass.

Cream cheese and jelly. I would open my lunch and there would be like a half-eaten apple. My parents, I was the youngest of six, so they were just over it. You know what I mean? My dad would take a bite out of an apple, put it in a lunch box, like my little smurfette, little egg that I had. And then I'd open up and then it would be like an egg that it would be like a not hard-boiled actual egg in my lunchbox.

That's how over medium. Talk about neglect. I mean, yeah. Wait, you have five siblings? Yes. Wow. Yeah, I'm the youngest of six, which is exactly the place I want to be in my family because I'm the youngest, but I'm also in charge.

Fair. I know what's up and that, you know, they have to listen to me. Otherwise, it's a wrap. I'm only the youngest of two and that makes a difference. If there was six. Right, right. Six is different. That does shape who you are.

I think so many people, like you are one of my favorite people to follow on Instagram, just the skits you do about just men or. politics or anything you bring humor but so many facts and like good points and you're my favorite person to follow for that kind of thing and I imagine your book is going to be similar to this tell me about it well my book was I was I got this book deal when I was I was I had fallen in love with Joe Coy publicly very publicly okay this guy that I dated he was a comedian and we were like you know head over heels and love and blah blah and this editor reached out and was like well I would love to hear the Chelsea Handler version of a love story because you're obviously in love

this is very unexpected that you're singing from the rooftops of Instagram talking about your love and I was like yes I am in love I want to write about it I can't believe I get this to you in this life like I feel so grateful and fortunate already with everything that I've been able to do and I'm not

somebody who's ever wanted to be married or have children so like men in my life have never been the epicenter do you know what I mean? It's a side piece like it's you're part of the they're not my story you're part of the story yeah so when I fell in love with Jo Koi, I was like, oh, God, you know, I have so much to say about this.

I was like, my whole heart opens up, you know? And then we broke up, and I was like, oh, whoopsie-doodle. Like, I don't know what this book is going to be about? And then my editor's like, what about writing about your breakup? Because I had handled it in a more graceful way than I had ever handled a breakup before. You know, I wasn't telling anyone what happened. I didn't throw anyone under the bus. I didn't kind of publicly embarrassed or do anything like that.

Did you want to? No, no. I just, I'm older and you're more mature now, and I'm more, you know. I just don't need to do that. I just, I don't want to do that. That's a bad habit, you know, that I've done enough. Although there is a little shout out to him in my comedy special, my Netflix special, which will be out next month.

But not a shout out to him, but, you know, a kind of a joke about him. Yeah. But anyway, other than that, I was trying to remain, you know, just really mature and loving and not to slam the door shut, you know, and never look at, like, to keep the door open in an act of love and compassion and understanding for the other person. and as a just nice act of maturity on my own behalf. Right. And then I was like, I don't want to write a book about that

because, again, he's part of my story. He's not my story. Yep. So I just kind of set, like, let it, you know, I just left it alone for a few months, like about nine months. Like, you know, I was having a pregnancy idea at party. Like, I was like, okay, I have to impregnate myself with an idea for a book. And then I just was inspired by the idea of what my life is.

and the life that I've created for myself by being truthful, by being honest, by never pretending to be something that I'm not, by taking so much shit from men my whole life because I don't fit into the mold, you know, that you're told is of value, which is to be a wife and to be a mother and to be quiet and to be pretty and to be thin.

You know, all of those things, I was always just like, fuck you. I'm not going to do what any man tells me to do. Like, anytime men tell me to do something, I almost want to do the opposite. I feel that. And in many times I do. You know, when I bought my house in Majorca, I bought this, this beautiful house, which is one of the best things I've ever done in my life.

I talk about this in the book. And I bought it in Majorca and I had consulted with my business manager about it. I was like, oh, I found this house. I'm going to redo it. It's right on the water in myorka. This is like a really bad decision. You know, you can't. The Spanish economy did it. I'm like, forget about that. Yeah. This is what is happening right now. And the more you tell me no, the more I'm going to do it. Meanwhile, the Spanish economy turned around in a year. The whole place I bought turned around. around in a year. Like, I bought this house. I did it. It's fabulous. And then the whole port that I live in all kind of judged their houses up. And so like the property value has increased. I've written two books at that house. I've supplied so many of my friends and family with amazing vacations there. And like I, you know, that was an example of just like grabbing life by the balls. I just finished Chelsea lately. I'm like, I deserve a present. I've worked my ass off for the last eight years.

And I want a gift to myself. And the book is about that. It's about getting after it. And like, being the best version of yourself, being responsible about your self-awareness and your growth and your evolution, but also being a sister. Being a sister to all women and anyone who does not feel seen, showing up in ways that, you know, people aren't necessarily expected to do unless you're a family member. And what that kind of yields in life when you are loving and generous, like generous, when you are, I was going to say, munificent. And then I was like, that's too big of a word for right now in this moment, I think. Sometimes I throw out these words and people like,

who the f*** do you think you are? I'm like, do you understand how much reading I do? Like, you know, when you host a podcast, I have to read like three books a week. I mean, Mel Robbins, you just had her on. I have her coming on my podcast. I watched two TED Talks. I read, I watched a documentary.

Yeah, you go to your research. I'm like, oh, God. I feel like I live with her. You know what I mean? How do you feel about turning 50? because I feel like 50 is such a cool milestone, 40, I'm excited. I'm 39 and everyone gets freaked out to turn 40. I'm not because I look up to women like you who are just like owning where they are at.

I'm not married. I don't have kids. I don't know what my future holds. But I'm just like, it doesn't matter because I'm just going to be true to myself and not follow the path that other people think I should follow. So does 50 feel even better than 40? I mean, I'm stronger than I was when I was 40 physically. like stronger like you are strong I go at it at the gym in a ways like I have the body that I wanted when I was 20 now that I'm 50 I have that body like I'm not you know so that that aspect of things on the material side of things is good I feel like I look great I'm healthy I take very good care of myself and it's not bullshit what everybody says about aging and how you become more confident like you know having sex you do what you tell people what you want and then they do it you know what I mean like when I was 20 I didn't know how I was faking orgasms I was like wait oh oh

Is he okay? Like, such a dumbass, you know? Same. And then you think you're supposed to be doing what they do in the porn? So you're just like making wild noises and like thinking you need to be like contorting to these just to, you don't know what you're doing. Yeah, no, you don't know what you're doing. So for me, I think the celebration, I have no problem aging.

I'm totally down with it. 50, I don't go, uh, yeah. I can't believe I'm old. I'm like, oh my God, this is awesome. I'm redefining what 50 is for me. Like, I didn't think this was going to be what 50 was. I'd be retired and you know I'm touring all the time I'm on my set this is my seventh book holy my seventh book like I think the thing that I get prideful about with regard to my own growth

is again just the fact that I've never let people tell me how to behave yeah where does that come from how do you get that I don't know but I I want to infuse any woman I can with it because it's I think I was just born that way with this like kind of false confidence and then it becomes real And you're like, I am confident. Why, I have no reason not to be confident. Right. I have this really fun life, this life that I dreamed about when I was a little girl. And the book starts out with like an essay that I wrote.

I didn't write it when I was a little girl, but it was like this daydream I had about, I would daydream about the kind of woman I wanted to be when I grew up. And I wanted to be loud and brave and stand up for things. And I wanted to have lots of lovers. And I wanted to have lots of adventures. And I wanted to speak another language. And I wanted to travel the world. and all those things are true.

And I am about to lead, like I've been in Whistler for a month skiing, and I am about to, you know, have a really big year commemorating this milestone birthday. So I'm pretty happy about life, my life. And I want other women to feel, you know, like anything is possible when you really work hard and you are thoughtful about what you're doing and you're intentional. Yeah. about being brave and being you know bold yes I think the real true like meaning of like our purpose and our life is to be truly who we are like yeah who are you yeah get like real with

yourself and find out what your personalities what do you like like when I discovered I love skiing I'm like I'm going to get so good at skiing yeah like I'm going to make sure I'm going to pay someone yeah to make me like the best skier I can be and that like became this now I have a house and whistler I go there you know for three months sometimes a year i need to find a canadian man i have one and i mean hello what do you think i'm doing around here i this is i'm already telling you what kind of life i'm needing and you have to have one for the mountains you have to have one for the city you have to have one for the beach there are all sorts of men flying around no shortage of that that is amazing is he canadian the mountain man by the mountains is yeah he's Canadian yes love that that's so fun and would

you say this book is I think I heard you say that it's a tribute to your fans it's a true yeah it's a tribute to yeah totally everything I do is a tribute to my fans yeah they gave me a career and yeah I've been doing this now for 25 years I think probably longer I'm 40 and I'll be 50 yeah no and um yeah it's a tribute to my fans it's the title I'll have what she's having was given to me by my editor she read the book and was like okay I have a title for you yeah it's like at the end of it you want what you have. Yeah. Or you want to get like, you know, get after things in the same way that you have. And I was like, I don't know if I can name a book. I'll have what she's having. I'm talking about myself. And so, and she, and then everyone else read and they're like, no, that's the title.

Really? So I was like, okay, I can, you know, I'm old enough now to not be so obstinate with my opinions about my own stuff. Yeah. Where I take some feedback, you know? Yeah. Especially from women. I always appreciate feedback from other women. Do you get nervous still about releasing? Because this is what You said your seventh book. Do you get nervous releasing books about what other people are going to think? Or do you just do it because you're like, I believe in this book. Yeah, I mean, I think you just have to put all your positivity right in your basket. You know what I mean?

It's like a bowling ball of energy. You believe in it. You love it. You put it out there. Yeah. And then the energy and like kind of force behind it is so powerful. Nothing can really stand in its way. Right.

You just kind of go and bowl. And then it's going to be a success, hopefully. And if not, then, okay, that's not, but I mean, it will be. It will. Well, I know for a fact it will be. And I want to talk about the fact that you moved to L.A. at 19 to live with your aunt in Bel Air. It feels like from the moment you made it to L.A., you kept getting into these, like, hilarious situations and playing pickleball with, like, royalty or having dinner with Woody Allen. Like, do you think you just put yourself in positions that not a lot of people would as you go for things?

and it ends up working out for you because not a lot of other like for example one of my friends is a motivational speaker about doing things that you want to do before you die or having this bucket list and he says that the options are so much more available to people that put themselves out there because not a lot of people are doing this do you think like you're just do you know what I'm saying absolutely no absolutely yeah I'm open like I'm not a I'm not a closed off person so right if you say we're going away for the weekend first of all I'm not a control freak I don't have Like, I'm a type A from about 8 a.m. to 11 a.m. and then I'm a type C. I don't give a shit. Like, I work for three hours a day pretty much, hardcore, and then I'm done. Yeah. And I'm open to anything.

So if my friends say, hey, we're going away for a weekend, pack your bags. I don't ask any questions. I don't want to be involved in any logistical planning. That is not my Medell. My strength is showing up and being open and having a great time wherever I go. Yeah. And that pretty much serves me well. The reason I get into these ridiculous situations is probably because I'm just a public person and I get more opportunities to be around, you know, other public figures. But I don't ever take myself too seriously. And so all the stories in the book about like playing pickleball Kenny Bunkport or my Woody Allen dinner party story, those are all in the book and those are all situations I just kind of found myself in. What was like your big break moment? My big break moment. My big

break moment. I mean, there were so many moments. There was never one big break. Really? I was on a show Girls Behaving Badly before Chelsea Lately. And that was like a little stepping stone. I published my first book, My Horizontal Life, a collection of one night stands when I was doing Girls Behaving Badly. And then when I got Chelsea Lately, I had another book come out. And that was kind of this like, you know, it was a kind of big moment. And then it became really, really successful, like well known, I guess. But before that, it was just a bunch of of little successes you know you're just kind of like stacking up wins yeah yeah a lot of a lot of rejection and but you got to be okay with that like you cannot get upset about rejection yeah

i feel like i grew up trying to be a dancer and i'm in my 20s like i moved to vancouver to dance like that's what i thought i was going to do and i had the false confidence i was like i'm the best dancer i'm obviously going to get whatever i want in this world and the rejection over and over and over. I was like, oh my gosh. And I had to give up my dance career because I was like, I'm just not good enough. So I went on The Bachelor. Oh, hold on. Thank God for that. Right. Thank God for that. And then I really knew what it was like to feel publicly rejected. Assailed. Yeah. Assailed. I feel like that show is really bad for women. I mean, what are the chances that that many women are going to walk in and see one guy and all we're all going to be attracted to that guy? I mean, give me a

break. It's brainwashing. Yeah. It's, you know, it's the thing you walk in and you go, it's a competition. Did I really want to live in Iowa for the farmer Chris Souls who like, no. But as soon as I got there, I was like, I'm obsessed with him because everyone else was. And the producers are putting them on this pedestal. And everyone's making you think that they're just God's gift to women. And I'm like, oh, my God. And I fell for it.

I totally fell for it. Oh, God. And then as soon as you get out of it. It's like a cult. It is. And as soon as you get out of it, you're like, oh, what? to you like wake up and smack yourself and you go back to talking to your friends and family and people that you actually like like and ground you and took me two days to get over

who I thought I was going to marry yeah two days yeah because I was out of the bubble right of course I just you know that girl Bethany Joy Lenz she just wrote a book about being in a cult she was on one tree hill no yeah I just talked to her because she has a new book out too and she I was learning about I'm not in a cults like I don't like to even hear like watch documentaries I don't like that vibe. You know what I mean? Yeah. It's just too.

But I had to read this book because she was coming on the podcast. And it was very, very interesting that you could be in real life and also be a part of this cult. Like those two things were dovetailing together. Right. Like, wake up.

Yeah, yeah. You have real people around you when you go to work. And then she was flying back and forward to this farm in Idaho. And that was where the cult family was. And it was just like, oh, God. I hate all of that shit. I will say Bachelor does feel a bit culty. Mm-hmm.

Yeah. Even the outside world of it with like Bachelor Nation and people, they all hang, they only hang out with each other. And like it's, it turns into this whole thing. Right. But I feel like that's reality TV in general. I feel like it's, it's all a bit, it's just manipulative, right? It's manipulating people. And it's, it's a freaky thing. But I'll do it again. I would host again. I wouldn't do the show again. In your book, you talk about sexing with a governor. Can we talk about that? Governor Cuomo during COVID. I was very turned on by him sexually. Really? Yes. And I went on the view to declare my love for him. And what happened? How did it end? I said I would like to be penetrated by the governor of New York. I just wanted to put it out there into the ether of like, you know, so that he would hear.

Yeah. And he heard about it. And then he called me. And then we flirted and sexted and texted. Not sexted. I don't, I never do that. What is sexting? I guess eat my pussy.

Like, I guess that's sexting or like, I want to suck your dick. I don't know. I don't do that. I don't really do that anyway. Like, that's not my style. I'm not putting shit like. that into writing so that Elon Musk can hack my phone and spread it all over the world. I know.

But no, it was very fun. It was a total Chelsea story because I always get myself into situations that are either really hard to get out of or I've been extricate. My sister has this theory that she thinks my mom, my dead mother, is upstairs in heaven just making sure I don't get canceled. Like she's basically working double time. She's like Chris Jenner up there. Yeah.

My mom's acting like Chris Jenner in heaven. And she's basically walking around making sure I don't fuck up my life. And my sister's like, you're requiring too much of mom's time. Like, mom, I want my dead mother around. And I'm like, I feel mom around me all the time. She's like, I bet you do. And I'm like, I think that's really funny. That's how you think mom is spending her time in heaven by cock blocking me on the ground.

Like, okay? That's a very interesting perspective. But you do feel her around? I do sometimes. Not recently. But I guess I always kind of feel my mom around. But, I mean, it's funny. My mom passed away and I, like, have a closer relationship with her now than when she was alive.

Interesting. I was always close with my mom, but I was always super independent. Yes. I was never, unless I was like, you know, eight years old. I just kind of grew up very fast. When you have five brothers and sisters, you know, I started running my own business when I was like eight years old. I had a hard lemonade stand and I made a lot of money. Yeah. And then when I was 10, I had a babysitting company and I lied. I said I was 15 because I looked older and I was only 10. But and I ended up babysitting for a 14 year old boy that whole summer. Stop. Yeah. So I was very entrepreneurial. You always have been. Like at eight, you wanted to create your own lemonade stand. Like it wasn't your parents being like, you should do this to work. Are you kidding? I was just like, where's the alcohol? I want to do a hard lemonade stand. I want to serve gin, whiskey, and tequila if I'm going to make any sort of profit margin.

My parents are like, you can't sell alcohol. It's legal. I'm like, okay, anyway. I didn't listen to it. I knew my family and I were not on the same page. Like I had big ideas and big plans and they were not part of those plans. They're in my life now because I can't shake them because of my brothers and sisters and all of the kids that they have procreated.

So I have, you know, a huge family and I love them, but I knew right away, like the lifestyle that I was born into wasn't going to cut it. Right. Well, it's funny that you say your mom's up there doing PR because your comedy is always kind of push boundaries, which I always think for comedians, I was so scared for them when everybody got so sensitive because I feel like everybody was getting canceled and this and that. But I feel like you balance this act of like edgy with evolving humor. Like you're able to evolve with the humor and social norms. I feel like you're able to do that. How do you think you do that? Like how do you get away with it and why do other people get canceled so quickly? Well, A, I think, I don't think, I don't have the same viewpoint that all these comedians who are complaining about cancel culture have.

A, it's nice to know if you're hurting someone's feelings. Right. It's nice to learn and not do that or not discriminate against a group of people who are our, already, you know, are in a community that are being targeted. Right. It's nice to respect people's boundaries. It actually makes you more clever and makes you smarter as a comedian if you can respect other people's boundaries.

So I welcome any notes. I am, you know, I'm always willing to understand that I may have not acted with the best integrity and that I can do better, but maintain like a loving kindness while you're being funny, you know? That's not an issue. Like for me, I am edgy and I am, you know, harsh and loud and all of the things that have been attributed to me at one time or another, I have been all of those things. But that doesn't make me, I don't have to worry about what I'm saying because I'm not an asshole. Like, I don't

have to go, oh God, don't, I'm going to get canceled. No, I'm not going to get canceled because I'm not an idiot. Yeah. That's a good point. You're smart and funny and you're a good person. My mom always was worried and actually certain friends are like, I can't believe you haven't been canceled yet because I'd say what I think and I say what's on my mind. And I'm like, but it's the same thing. I'm like, I'm not a dick. I'm not a complete idiot who doesn't know what she's saying and like we'll make like a comment that is inappropriate. Oh, I make a lot of inappropriate jokes. But I feel like you know, you still know right and wrong.

But inappropriate is okay as long as it's not crossing a line, you know, where you're not sexually harassing someone or diminishing someone's, you know, feeling. or person, like, personhood. Does the balance for you just come naturally with comedy to be able to do both, kind of? Yeah, I mean, I'm very self-effacing. So, like, when you start out making fun of yourself, you can make fun of other people. Yeah.

And it doesn't, I don't want to say gentle because that's not, like, my comedy isn't gentle. It's, it's my person. I'm telling all of my stories. Like, that's my, that's my style. I'm a storyteller. When I write my books, they are stories. When I do my stand-up, I'm telling stories.

that's what I'm good at. Yeah. So when you're telling stories, it's easy to figure out how to like, you know, find the punchline or make the joke about you or, you know, make the joke about someone else without tearing them a new asshole. You know what I mean? Unless they are an asshole and then they deserve to be torn a new asshole. You know what I mean?

There are people out there that deserve it. Absolutely. And you do such a good job at that too. That's shop, B-E-A-M-com slash Vine and use code Vine for up to 40% off. You were one of the only, you were the only female late-night host for years. Looking back, what do you think your biggest challenge was that you faced as being the only woman in that industry? I didn't find it challenging. I honestly did not.

I didn't think about me as myself as being the only woman. That was only a question that everyone asked me all the time, that I was like, what? as if I want everyone to listen to this like as if being in that position having my own late night show shooting at five days a week as if I have time to think about what it's like to be the only woman as if I have time to go I wonder if Jimmy Fallon or Jimmy Kimmel or Jimmy Jimmy Jimmy yeah whatever like why why would I be doing that right I'm having a good time shooting a show we're laughing our asses off it was never an issue for me in fact it was probably easier because I stood out because I was the only woman.

So I remember being asked that question so many times during my, I think it was seven years, I was on E. And I always was like, I'm not thinking about that, you guys. It's not a competition for me. I guess I was just more thinking like did people in that space treat you differently. I mean, I was on the E network. So it's not like, you know, there was a lot of, I also was dating the president of E, you know,

after the first like few months of being there and my, the guy that was that I was dating the president, he was the person who originally hired me for a show before Chelsea Lately I did like a short-lived show called the Chelsea Handler show and then we turned it into Chelsea Lately because that show wasn't successful

and it was more like sketch. So they were like you should do your own job and then so he and I got together and he I would just argue anytime there was any fight I would just you know I had no problems going straight to the top and being like I'm not I'm going to say this

bleak me out like this show is funny because we do say you know like it's ridiculous unappropriate bleep us it's so fun and and you know I would win a lot of arguments because it was my boss but I would have to have like arguments with standards and practices but I didn't no I didn't get treated differently differently that I know of but again that's focusing on what other people are doing with me yeah I'm focusing on what I'm doing with myself I'm not worried about what if they're treating me differently because I wouldn't know the difference right God I want to be you when I

grow up I want to talk about your podcast dear Chelsea what is the most unexpected advice you've given on your podcast and did it work out? I've given a lot of advice on my podcast. I went to therapy for two years, hardcore, and I learned a lot. And I went to someone who's cost a lot of money that I know most people wouldn't be able to afford. And so when I got out of therapy, I wanted to share all of my learnings with every person that would listen.

I was like, listen, I learned so much about my personality. I learned so much about, you know, being gentle and being empathetic and being versus being compassionate and actually being too harsh and understanding how you come across, that I just wanted to like apply that. You know, and so I started my podcast, you know, when they gave me a podcast deal, I was like, I'm not doing a podcast. Everyone's doing podcast. What am I going to do? I'm not going to interview celebrities. Like, I'm not interested. I just did that for 10 years. Right. First on E and then on Netflix. And then I was like, oh, I really love talking to regular people. I was like, oh, maybe we should do like a Dear Abby where people call in. And I'm very unfiltered as anyone who knows me knows. And I'm objective because I'm not involved in these people's lives. So when they call in for questions or advice, I'm, I'm very straightforward and I'm very like, so what was the most unexpected? I guess one of the first callers that called in in the beginning of the podcast, which was like three years ago or four years ago, was looking to take a break from smoking pot.

He's like, I smoke too much pot and I love smoking pot. And he was like, I just am smoking too much. And there's a fine line. Like when you overdo anything, it's just no longer fun. Right. And so I said, oh, let me do a challenge with you. I'll take 30 days off. You take 30 days off and get your head clear.

because he's like my roommates all smoke pot like I just feel like my life isn't where I want it to be I'm depressed it's making me more depressed creating anxiety so he quit for 30 days yeah and at the end of the 30 days he moved out of his apartment came out as trans to his parents and transitioned nice and he and yeah and he's like I yeah that was like incredible so I mean I didn't know when I gave him the advice I'll do a 30 day break with you well let's chat in 30 days and see what happened right and he revealed all that of that and you know like so he was smoking all that pot to avoid his feelings to avoid having to talk to his family to avoid his truth yeah and i don't know why i had to take 30 days off of a pot

but you know the sacrifice was worth it i think i did more like 28 you know what i mean i didn't quite make it but i did it's pretty good i did it in the spirit of like you've got a buddy in me i'm going to be your big sister in this moment i will help you and let's figure out the truth like what is the truth what is going on with you and so that was really like gratifying and moving to know about and hear about and yeah we get a lot of notes of people who are like thank you so much like i you know if you need to get out of a relationship sometimes you just need someone that doesn't know you to tell you yeah i agree with that also this triggered my memory for smoking weed last night i took i was in new york i got these edibles it was to sleep last night it did the opposite for me

i hate that the guy was like i take two and i was like i'm going to take half and just see how i feel and then i'll take the other half i ate all of my hotel snacks like the cookies, the beef jerky, the everything that was in that snack, the half bottle of wine. I was like, everything tastes so good right now from half a gummy. Yeah. And did you go to sleep after you ate all that? Yeah. Oh, well, then it worked. But it was like two hours after. Yeah, but you know, you have to say to yourself, I listen, I have this problem with edibles because I love edibles and I can't really smoke because my throat gets wee-I'm wheezy right now because I had one hit off of a joint this weekend in Vegas. I have a residency there, so I was performing.

She's amazing. And I was like, oh, give me a hit of weed. And my cousin looks at me every time I do this. She's like, please don't. You're going to be wheezing for the next two days. And you can even hear it. I'm like, so I can't really smoke that much pot. Even though I love smoking pot, I do take edibles.

But I always say this to myself. And this helps and it works. Okay. For anyone who's listening who loves edibles, when you take an edible, first of all, I always take them after I eat so that I don't want to eat. That won't stop me. But you also have to say, don't be a pig after you eat this edible. You're going to be hot.

and don't be a pig. And for some reason, that works. I wish that worked for me because I was saying it before. I was saying it during. I was saying it when I wanted to go back for like fifths of the cookies. Like I was like, this is disgusting. I know. But that's when you don't, you have to have the intentional when you take cannabis.

You have to know that you're going to want to do that and you're going to get the munchies. It's very unusual to not get the munchies when you have an edible. Oh, well, when I was, I think I was like 25, 26 living in Vancouver. and I went through the smoking weed phase because they had really good weed in Vancouver and I got all my best drugs in Canada yeah oh 100% and I would lay out a veggie tray like I would just

and I would just go from different veggies because I knew I was going to be a pig otherwise and then you wanted vegetables when you were high I didn't but that's what I would choose to stuff my face with. Oh well that's smart I guess yeah but you can't do that in a hotel at one in the morning when there's with crudite no you can't I couldn't there's so many delicious

okay you talked about your residency that cosmopolitan right cosmopolitan yes the Chelsea I perform at the Chelsea I'm Chelsea at the Chelsea it's called Chelsea at Chelsea how does that feel to have a residency in Vegas it's awesome it's so fun I mean I it's not of your traditional residency I perform once a month so I'm like there in January I'm in there in March I'm there you know I do like on big holidays and for the next two years so every time I go we make it like an event and I bring out like friends or family you know and we go we have fun we gamble and we make like a night or a weekend out of it so wait that's ideal to just go once a month yeah totally so do you live in l.A and so that's also really close that's so

fun Chelsea at the Chelsea once a month yeah that's I want to come watch come anytime how long is it for like when does it the residency end or is like two years yeah that's awesome I know it's so fun oh my gosh do you how do you recharge your batteries oh my god you don't even know. I mean, I am at the end of my rope right now. Oh, shit. I am at the end of my rope. Thank you for being here. Of course. No, but I had a good night's sleep. Like, A, it's the sleep is the most key ingredient for me. Like, I need to always, and I'm just, you know, sometimes you're burning at both ends. Yeah. And it's hard. It's hard to like, but I take long breaks. Like I, you know, I take a month off. And then I go on tour for, I'll be doing a

European tour this year. Oh, wow. That's huge. I'll do that for probably six weeks straight. And then I will take two months off. Like, I'm very good about going to Whistler or going to Majorca or going on vacation. And that is as important to me as working. You know, I work really hard so that I can relax really hard. Yeah, but you've worked hard to get to that point that you can do that. Yeah, like I hustle so hard to get that month off. Yeah. That by the end of the hustle, I'm ready to like, you know, take a bunch of Xanax and sleep for a week. Sounds like a great. I need to get into like my hyperbaric chamber for like two weeks and just Michael jacks in it is that what like like your downtime when you're doing that month off like what does a day

look like skiing yeah yeah yeah ski ski you know and have i have a ton of like a group of friends up there and it's just chill ski appre margaritas chill bed early up early all of that you've been like really candid about your love and heartbreak but what is the biggest misconception people have about you and relationships i don't know what they would think I mean, I don't know what people think about me in relationships. Okay, well, just maybe what's the biggest misconception about you in general? But that's me associating with other people's thoughts of me. So you would have to tell me what people think about me because I'm not that invested in it.

That's the best answer I could possibly ask for. I love that. Like what? I mean, I don't know what people think about me. This is why you're an inspiration online because I want to get to that point. You will. I promise. Really?

Yeah, you will. It's just age. Well, yeah. Listen, everyone's dealt a card. We all have reservoirs of resilience and confidence and hopefulness and optimism within us. It's just a matter of whether or not we choose to go and get like tap into that or we choose to listen to all the negative thought patterns we have and all the insecurities. And once you learn how to stop thinking about the negativity and start focusing on the positivity, it's not that big of a contest, which part of yourself you listen to. Having all these negative thoughts about yourself, repeating them to yourself, having low self-esteem, not how.

Having a good self-image isn't doing you any favors. Right. You can fake it until you make it. You can act like you're successful before you're successful. I believe that works. I believe you can act like you have confidence before you have confidence. And eventually you'll have confidence. Yeah.

So all of it is just like there's like a big metaphysical aspect to it to actually having like, you know, good energy and being a proponent of good energy and making sure, you know, and listen, not everybody can be positive to 24 hours a day. I certainly cannot. Yeah. But I know now myself enough to know when I have to withdraw and when I need to be alone to recalibrate. You know, if I'm going to do three shows in a weekend, which happens very frequently, by the end of the three shows, I'm sapped. You know what I mean? I'm going to, I'm sapped. I've given, expended so much energy. There's thousands of people at my shows, you know, I want to make sure everyone's having a good time. So sometimes, you know,

it's harder, but you also have to identify when you have something to give and when you don't. And When you don't, that's okay. You just need to, like, rest, sleep and store it back up. The thing that actually helps me, and I've talked about this before, is my assistant has my schedule for my period. And I do not even ask me to do anything five days before it. Like, I need to be in bed during it. And that's actually been really helpful to somewhat find some balance.

To know why you're in a mood or why, yeah, to identify what the problem is. Because I get, I have PMDD and PCOS, and it's just like, you're looking at me. Are you a person of color? What is PCOS? It's like polycystic, ovary, something. But I have like major fibroids and like it's so painful. Oh, sorry. No, it's, I'm like, it is what it is.

But it is so I like black out from pain sometimes. Oh, God. Yeah, it's terrible. And then I also on top of it get like horrible hormonal depression. And so it's just like a double. whammy of being in pain can't get out of bed and like intrusive thoughts it's awful it's awful it's just clockwork every month i'm like here we go again oh sorry you should get an ablation what what will that do well an ablation stops i got one an ablation stops your period so your uter lining you don't get

the cramps and the fibroids would tamp down a lot so you don't bleed every month you don't get a period which obviously is ideal yeah yeah you know especially if you're planning on not having children because you you you I mean it's not a hundred percent sure you won't get pregnant again but you most likely won't really um so you can't bleed so like that whole you know where all your cramps come from and all of that so you don't get cramps or anything no no do you get like um any hormonal like imbalances i'm sure something's wrong but you know like i can feel my boobs getting swollen yeah yeah yeah yeah so i'm like i know i'm getting a period still because i'm in perimenopause of 49 no i've never dealt with what you've dealt with though because that sounds really nightmarish it's

So awful being a woman sometimes, you know, like, I mean, I can't believe we're expected to get our periods and deal with that. Like, are you kidding? It's so gross having to deal with that every month. It's awful. And it's the fact that it's not even every month. It's like every 23 days. It's just absolutely terrible. So I always make my guests do some sort of confession with an embarrassing story. But have you ever had anything embarrassing happen on stage to you? I mean, I once had explosive diarrhea. I was performing. But I have, this isn't embarrassing because there is something. about getting on stage that pauses your like your adrenaline takes over and it puts whatever ailment you are dealing with or whatever malady you're up against it puts a pause on it yeah so I was like there's no way I'm going to make it through my set I'm on stage for at least an hour every night and I'm like I'm never going to make it and then I was just like okay well I have no choice I'm going up there and I was like oh and the minute I got off my ass exploded again so your body knows your body knows like put it on pause bitch okay we were you're a professional. That's so true. I really do feel like I've seen some like furgy. Didn't you peer pants during the like national anthem? So weird. Yeah. Yeah. I guess yeah. You really have to time that right. I don't know. But that's just kind of being an adult. Do you like maybe be before you go. I don't know. What is the biggest oops I shouldn't have said that moment on TV for you? Oh, I out my boyfriends a lot on TV. Like I forget that their stories are are theirs. You know, too? I always think I'm talking and I'm like, oh, I'm telling. I'm telling.

my story and then I don't realize it incriminates other people. So I was on Jimmy Fowell, or no, I was on Andy Cohen's radio show and I was talking about my boyfriend Ted Harbert, the one from E. Yeah. He was asking if I had ever done threesomes and I was like, oh yeah, Ted and I used to do them all the time. We had a masseuse that would come over. She was awesome. And then I knew it was

time to break up when I started calling the masseuse when he was out of town. And he was like, oh my God, you know, and I was like I forgot I even did that show. Like three hours later I was out to dinner with my friends. Like I just didn't even think about it. Yeah. And then the next morning I was walking or the next afternoon I was in New York City and I was walking and meet some friends for brunch and my phone is blowing up blowing up like vibrating and I'm walking and I had this Apple's stupid

watch on that never works and I was like what you know and I and then I saw a text from Ted Harvard or an email from Ted Harvard and he said please don't ever do that again some things are private oh no I was like what's he talking about I was like that's a pretty stern email to get from my ex yeah and then I was like what could he I was like racking my brain sitting there on like Fifth Avenue walking going what what did I do where have I been recently and I was like did I say something publicly and then I was like I googled myself yeah and it's like Chelsea handler talks about having threesomes with ex-boyfriend and why she left him for the masseuse like so bad then I went on Jimmy Fallon like a few months later and I was like hey I want to clear up that

story about Ted Harbor because Jimmy Ted was Jimmy Supposed at one point too and then I ended up just doubling down I was like listen the breakup wasn't because of the masseuse but we definitely had a good time. And I go, and quite frankly, I'm giving him a lot of street cred, because nobody would have ever guessed that Ted Harbert was doing three subs. So why don't you go fuck yourself, Ted? And then the next morning, I got an email from Ted, and he goes, thanks, I think, question mark. So, yeah, I do that shit. Like, you know, that's a bad habit to break, an old habit to break, because I'm such a truth teller that I always forget. Sometimes I can't tell other people's stories. They're not just mine.

Who's someone that you've met who made you think all have what they're having and why? God, this is a great question because, honestly, I want to answer this in a very thoughtful way. Because, again, this goes back to really being who you are. Yeah. So if you really are invested in who you are and who you want to be and that whole process, you really don't want to ever be anyone else. You know what I mean? You can look at someone's life and go, ooh, I wish I had that, or I wish I was, doing that, but do you ever want to look at someone and go, I wish I were that person or I wish

I was that person? I don't think so. I don't want girls to think like that. Right. I want girls to see other women doing things and going, oh my God, instead of envy. I mean, you can be envious. That's a human emotion, but you don't act on envy. Right. You act on motivation. Like, that's motivating. I want to, I want to live a life like that. I want to be free like her. I want to be, you know, I want to have the outfits or wardrobe she has. So get after it that way. But I don't ever want anyone to try to be other people. I really think like that is what is lacking is our identity. You know, you really have to be invested in yourself.

Like, how am I going to get to the next best version of me? Yeah. I feel like, yeah, so many people look at others as competition instead of inspiration. And I feel like I always have to kind of like in the moment realize when I'm doing that even myself. And I do it, but I'll be like, I'm aware that I'm doing it. So then I switch it. What is one adventure you'd recommend everyone try at least once? Well, sex with a stranger.

Safari. Safari is a great adventure. That's all my bucket. I've been on the safari three times. Best things I've ever, the best trips ever, just unforgettable memories. And it's so beautiful to see that part of the world. Yeah. Another adventure.

I mean, I love adventure. I love newness and freshness and risk taking. And I like to be scared. Yeah. So I like to be scared and then like, you know, walk right into that fear and make things happen. There's just such a rush that comes from that and I'm an adrenaline junkie. So I really, I don't like to be scared where it's debilitating or, you know, I'm shaking or something. Right. But I like to challenge myself and always kind of, you know, do the thing that's a little bit harder.

I feel like you do that a lot with like stepping outside of the comfort zone or the box to get yourself ahead and it always works. Like it always, you know, you always learn something from it or get ahead in some way. whether that be, like, mentally or physically or professionally. And also, it's not just about you. Like, I want to say that also to everyone who's listening. Like, it's not just about you getting ahead. And, you know, sometimes, and I write about this in the book, like, sometimes you're not the main character in the story.

Yeah. Sometimes you're there for someone else. And sometimes you're a character in their story. Yeah. And that's all right, too. It's not all about you, life. Right. It's about being the best version of yourself so that you are more accessible and to other.

and that you are caring and that you actually go out of your way in that way as well for other people, you know? Do you know that you have a good reputation with that? Like from people that I know in certain industries, you are a name that comes up always that of just how good of a person you are. Oh, great. Love that. Love it.

And just like how, yeah, you have like a really good reputation. Thank you. Yeah, yeah. I know a lot of people that know you. And everybody was like, oh my gosh, you would love her. She's so herself. she's so this she gives to other people she's very generous and yeah yeah thanks well that's because i always i live with my mother in my mind you know what is going to make my mother proud my mom was the

sweetest really sweetest person she was european and she was soft-spoken and she was demure she's everything that i am not and so she was like who is this lightning bolt bitch daughter that i have on my hands because i was hell on wheels from the moment i could like form a sentence i'm like this is not going to cut it people Oh, my gosh. So whenever I, you know, I always act with my mother in mind because my mom was the sweetest. Oh, I love that. Yeah. What is the wildest thing you've ever done to get ahead?

To get ahead? Yeah. These questions, I love asking you because you don't give bullshit answers. I had a situation once where I was with an old friend and there were two people that needed help. And one of the people that needed help could not do anything for either one of us, ever. Yeah. You know, was in a very weak spot, very insecure, very. very kind of traumatized and then there was another woman that didn't need our help but could do a lot

for us and me and that girl have never spoken again really because I stood with the underdog because that's the right thing to do yeah and she decided to go in a different direction when this was a friend for 20 20 years and I just remember looking thinking I don't ever want to be a person that tries to get ahead yeah like I'm going to get myself ahead I don't need anybody else to help me do that. And I feel like that's people with that mentality do get ahead, but it's in a more patient way and in a more authentic way. Yeah, and you don't, I can sleep at night. Yeah, and you can, I'm not, I'm not for sale, you know what I mean? There's a special place in hell for certain people like that. Like the, like, Bachelor producers always joke. I'm like, how do you sleep at night?

Oh, yeah, well, that is something other, that is other, otherness. Last question is, what is freedom to you? Freedom is skiing down a mountain top. or in a bikini with a joint in one hand, a margarita in my other hand, and a dog on my back. Freedom is riding my bike down the hills of Majorca when I'm on vacation with my friends, and we go out for these long, languorous lunches and we have lots of sangria and beautiful fish. And then we ride our bikes home, and we ride right into the ocean. Like, I live on this little block and we, and I just feel so free. Like, I see, freedom is not having a husband. It is not being tethered to another human being.

It is being free that I, so free that I can get on a plane tomorrow and go wherever the hell I want to go. And I don't have to check with anyone. Yeah, I feel that. Wow. That does sound like freedom. To wrap it up, what's next for you after this book? Are you going to do like a book tour? I'm going to do a book tour.

My special will come out on Netflix by the time this air is that will have been announced. So that will be coming out. Are we allowed to know what it's called? It's called The Feeling. Okay. That will come out March 25th and this will air probably in February, right? This is going to air it on your birthday. Oh, perfect.

Well, then, yeah, my special will come out next month, a month from today. I have lots of stuff lined up for this year. I bet you do. I do. It's going to be a busy year. That's great. And then I'm going to do my European tour because I haven't toured Europe in a while. So I feel like that, to be able to even just say, like, a European tour would be my dream.

Well, you are amazing. I love getting to talk to you. And I'm just, like, so grateful that you came on this podcast. I'm Caitlin Bristow. Your session is now ending. And if I'm being honest, I wouldn't mind a rating and review. gift appear. Gripping series like power and the game, next level comedies, music video channels, and more, brilliant black entertainment, intentionally curated, and all free. This month and always on

Pluto TV. Stream now. Pay never. I'm Stacey Schroeder, and honestly, you never know who or what you might hear on my podcast, Stasi, because, well, I'm a little cray-cray. One of the ways you know you have hashtag grown is when you come to the realization that Carrie Bradshaw is kind of the worst person. I've helped explain her that the fireplace grows so that Santa can fit in it. Now she's going to be like, well, there is no fireplace and we're in this

hotel and I'm going to have to explain her, I don't know, he gets a hotel room key, like all these things that you have to come up with. It's just kind of crazy. Should I bring a whistle to wherever I go? Do you think that that would be the thing to break the ice? Whistle. Listen up. Every single one of us here is feeling some.

level of social anxiety so let's just get on with it okay take a fucking breath relax so please do me a fave listen follow rate and review my podcast dossie wherever you get your podcasts