Mike Birbiglia's Working It Out - 177. Chelsea Handler: Why She Must Say It

Episode Date: July 14, 2025

Chelsea Handler has achieved massive success, from her latest Netflix special The Feeling to her worldwide tours to her Las Vegas residency. But as she discusses with Mike, and details in her new book I’ll Have What She’s Having, she wasn’t always on top of the world. Chelsea tells Mike about bombing badly at Just For Laughs, and how some advice from Jane Fonda helped her during a difficult time. Plus, the story of when Chelsea unintentionally drove a giant bag of cocaine across the country, and why she felt compelled to confront Woody Allen with a very dark joke.Please consider donating to the Carter Center

The decent and the right thing to do is to tell someone when they're slipping and to herald somebody when they're not. It's just sisterhood. You don't have to be best friends with everybody, but you have to be a sister. But you think that's a specifically female thing, like men don't have that thing.

I don't know what men are doing. I can only speak for myself. I wish I cared enough to think about what men were thinking and doing. That is the voice of the great Chelsea Handler. Man, I'm so excited today, because we have wanted to have Chelsea Handler on this podcast for so long.

We got to sit down and talk. We had a blast. Chelsea is, of course, one of the great stand-up comics working today. She's got a great new special on Netflix called The Feeling. She's got a great new book called I'll Have What She's Having. She does a residency in Las Vegas.

She just added three tour dates, West Hampton Beach, New York, Rochester, and Napa. Thank you to everyone for such nice notes about my special, The Good Life. It is on Netflix now. I've got five shows coming up this summer. I'm honored to be performing in support of John Mulaney's tour,

alongside Nick Kroll and Fred Armisen. We're doing New Haven, Connecticut, Bethel, New York, Portland, Maine, and Halifax in September, we'll be in Vancouver. Get tickets at birdbigs.com and sign up for the mailing list there to be the first to know about upcoming shows. I love this chat with Chelsea Hanley.

We talk about bombing and persevering and comedy and relationship deal-breakers and Chelsea shares new material about her plan to get marijuana through CSA. She tells the story of a time she drove a bag of cocaine the size of a pillow around America. That is a first for this podcast. We have a great time.

I love this episode, one of my favorites in a while. Enjoy my conversation with the great Chelsea Handler. I love that in your book you thank airline flight attendants. Yes. Because I feel that all the time. Feel that. Because I fly like you. I'm flying all the time for tour. We all do.

We all do. And you see these flight attendants and people say the craziest shit to them. And I think my theory on that is just like people are, they're not like you and I where we fly all the time for our job. Right. So they're at their peak anxiety and then they take it out on the flight attendants, it's the most insane thing.

Yeah, flight attendants are heroes in the sky. Yeah. They are doing the Lord's work. First of all, they took us through a pandemic where people refused to follow simple rules. There are men every single day that go on airplanes and take their shoes and socks off. That's what flight attendants are up against. And when you know something like that is happening,

how can you not empathize and sympathize with them and want to be on their side? Do you get thanked from flight attendants? All the time. That's nice. Yeah. That's gotta be a nice feeling. happening, how can you not empathize and sympathize with them and want to be on their side? Do you get thanked from flight attendants? All the time. That's nice. Yeah. That's gotta be a nice feeling.

Absolutely. Every time I get on a plane, they're like, thank you for what you say about us. I was like, of course, I've got your back. And I do, I do have their back. No, I know you do. I will go up and confront a person who's being rude to a flight attendant, I've done it before.

I'll do it again. I have no qualms about confrontation. I do not doubt that. I'm just telling your stories. What's funny, because it's like the George W. Bush story and even the Woody Allen, talking to Woody Allen story. There's a connective tissue of like, you will say, and the flight attendant stuff, like a bad passenger,

you will say kind of anything to anyone. It doesn't seem like there's a line. Well, that's not my directive. I'm not trying to say the thing that no one will say. I'm saying the thing that I must say. Right, with Woody, you asked him, how do you meet? How did you and Sunni meet? That's hilarious. To both of them.

I mean, that's so funny. Yeah, it was my day new mom for the evening. It's very dark. Well, but it's also very true. I wanted to remind them. That's hilarious. I mean, that's so funny. Yeah, it was my day new mom for the evening. It's very dark. Well, but it's also very true. I wanted to remind them of how they met in case they forgot. It's his daughter girlfriend. Adopted daughter.

It's his daughter girlfriend. Yeah, it's his daughter girlfriend. Wife. It's his daughter girlfriend wife. Yeah. It's the movie Chinatown. It's terrible. Yeah, yeah.

So you asked him, but then you don't say what he said. Did he kind of like filibuster away from that kind of thing? No, the pie flew out of his mouth. I had to time this very, once I saw that Woody Allen and Sun Ye were eating dinner with us, I was next to Katie Couric, and I was just like hitting her under the table going, no, no, like this isn't gonna go well.

There's no chance. There's no chance that I, as myself, I'm gonna sit across from him and his daughter wife and not tell him what I think. There's just on behalf of women everywhere, I will never be silent. Yeah, yeah. And so the next question was when am I gonna do it?

And Katie suggested in a mild way, is there any way you can wait? And I thought, wait for what? And she said, can you just wait till the end of dinner? And I thought that was a fun exercise because I had never waited before to tell somebody how. Yeah, good for you, good exercise for you. So that was fun for me.

Yeah, and then. I mean, it was hard, but it was a learning experience. Was it an actual, you're saying pie came out of his mouth, was it an actual spit take? I mean, he took a bite of his pie it was I believe it was blackberry cobbler and Everyone had the server had plated it and he took a bite and went Like he was laughing but I wasn't there for his reaction, right?

I was there to make sure he knew and everyone at the table knew how I felt before I left. Like, don't think I'm okay, I'm not okay with this. She didn't even know, she was kind of off in another world. She wasn't really landing. It wasn't even directed at her, it was directed at him. And Katie Couric was like, okay, I think it's time to go. Oh my God.

And the way she retells it, Katie wrote a book and in the book she told this story, but she told it in a way where she said, Chelsea did it, I don't think Chelsea remembered how Woody Allen and Sunni met each other because at the end of dinner, she asked them how they met. And I'm like, Katie, what? It's a well publicized.

What are you talking about? I didn't forget anything. Yeah. Have you ever had to go south, like talking to people, like saying what you must say? Yeah. And then it goes south, south? Yeah, but that's not my problem.

Right. You know, and I don't mean that in an arrogant way. It's like, if something's not true and someone says something to me, I don't, if it's not true, it's not personal to me. I'm not, if you say to me, oh, you're a narcissist. Okay, then you're free to think that. I don't have, I don't struggle with that, with thinking I're a narcissist. Okay, then you're free to think that. I don't struggle with that, with thinking I'm a narcissist.

You could say, you're an alcoholic. I also don't struggle with that label. That's fine if you think I'm an alcoholic. I'm not struggling with the notion of that. So it doesn't really matter unless you think it's true. Then that might be hurtful. If it's true, if there's truth in it, it would be hurtful and it really depends on the size of your ego,

which is something that is hard to not have in this industry. It's not like anyone can easily walk around and say they're egoless. I mean, even someone like you, who doesn't, I wouldn't say is an egocentric person. You don't project that. But it's hard to be in this business

with a microphone on stage alone and not be- Have some ounce of that. Well, it's a very strange profession. Right, to get on stage with a microphone and no one else is allowed to talk is a strange, is an interesting profession to choose. Something happened to make that happen. But you have so many wild stories.

You have this story, people should read your book and see your special because they're so good, but you have this story where you're moving out to LA and you had cocaine, like a bag of cocaine. So a pound of cocaine. So a pound of cocaine. Pounds, that's crazy. So a pound of cocaine and it's in your car

and the cops pull you over in Chicago, I want to say. Well, the guy that brought the cocaine, I had ditched in Maryland or outside of DC somewhere. Luckily, because when he said he wanted cocaine, I have no judgment about that. And at that time in my life, I hadn't ever, I've done plenty of cocaine somewhere, luckily, because when he said he wanted cocaine, I have no judgment about that. And at that time in my life, I hadn't ever, I've done plenty of cocaine in my life, but at that time in my life,

cocaine was of no interest to me. I was 19 years old, I wanted to move to LA. So when this guy who my brother met the night before at a bar, my brother being the protector that he is, said, oh, I met someone who can drive across country with you, I thought, wow, my brother's really looking out for me. And then I picked this lunatic up and he's like,

hey, I want to stop in Harlem. I'm just going to grab some, he didn't tell me he was grabbing cocaine, I don't think. He's just like, I want to stop in Harlem. Oh yeah, he said, I want to stop in Harlem. I want to get some Coke. And I'm like, okay, I'd never been to Harlem. Like Harlem excited me. I was like, God, I'd never been to Harlem. Like Harlem excited me.

I was like, God, I was never allowed to go to Harlem in high school. Sure. I'd love to go to Harlem, especially just for like quick, you know, ride through the city. Yeah. So we go, and when he said cocaine, I assumed he was talking about a dime bag.

Yeah. I'd seen plenty of those. But when he came out with what, it was like something I had seen out of a movie, like the biggest amount of cocaine in the world. The biggest amount. And I was like, oh, and then he started snorting it. And very quickly I deduced this was an unreliable driving partner.

And no one was gonna get in my way of going to California from New Jersey. No one. That was like your goal. Yeah, I was going to California, this guy was gonna be a protector because I was a young girl at 19. And I thought better to have a guy than to be alone.

And then once I met the guy, I thought better to be alone than to have this guy. So I ditched him, I let him out somewhere before I even got on the 66, cause I took the 66 and then many days later, well, not in many days, like 48 hours later, I was pulled over in Amarillo, Texas, in the Panhandle of Texas, by a state trooper. But the residue of the Coke was still in my car.

So the state trooper's dog went fucking ape shit. And I had to stand like 20 feet away from the car, on a freeway, like 18 wheelers are blowing past me, and I'm like, oh my God, I'm going to Texas State Prison. This is it. Like I didn't know enough about drugs at that point to know that they couldn't arrest me. I was like, I had a coke head in my car.

I was like, in my head, the wheels were turning, like what am I going to say when the dog finds any sort of residue of cocaine? Like I knew the guy had the coke and he was out, but who knows what he's going to find? And I was like, okay, this is my story. I picked up a guy, he had a gun in my head, I always had to like take the stakes to a level

that was so stupid. Meanwhile, the guy came back, he's like, well, I don't know what the dog went so crazy about, I'll let you go. And I was like, I mean, I stopped for gas once more and that was it. I was shaking for like 10 hours because at that stage in my life, I was for gas once more and that was it. I was shaking for like 10 hours because at that stage in my life,

I was scared of the police. Of course. Yes. Yeah. Oh my gosh. Yeah. Yeah, the amount of stories you have, do you ever feel like I'm gonna be out of stories soon?

Like the amount of great stories you have is uncanny. No, I don't, I don't like, well, thank you. But I don't ever worry about that because like I live a real life. I don't ever get so carried away with my career that I'm not able to experience real things. And just by virtue of the person that I am and the realness that I employ, I'm never not going to have those experiences because I'm open to everything.

It doesn't have to be a president. It doesn't have to be... You kind of say yes to life a lot. I'll go with the bus boy too on a boat ride, you know what I mean? To get the cocaine. I'll do whatever because I wanna have- You're skiing out a helicopter for god's sake. Yeah, I want all the experiences. There's a great story in your book about how Jane Fonda invited you over

and told you you needed to work on yourself. Do you still go to therapy? I haven't been to therapy consistently. No, not in a while. I've gone sporadically. Like if I have something that I'm struggling with or I have a decision or something's not going well and I need an outside opinion,

then I will talk to a therapist, but I don't have a regular therapy appointment and I probably talk to someone maybe once or twice a year. Do you think it, like when Jane Vonda said that to you, do you think it helped you? Yes. In what way? It gave me self-awareness.

It gave me a purview or a, like a look at myself from someone else who had nothing to gain by giving me that feedback. Right. Like it also demonstrated to me what sisterhood is, like how it is so important to be honest with women, as a woman, especially, because women have a habit of just not being up,

like having a hard time with any sort of conflict or confrontation. And I know for me personally coming up in this industry, it was very much a zero sum game for so many women. Like a lot of the people that cock blocked me were women. The people that wanted to stop my success were women. And I was so confounded by that. I was always like, what is this?

And when I started my original show where I had such success with Chelsea Lately, it was so important to never ever behave that way because I had experienced it so many times. I was like, I'm never gonna be a woman like that. So the demonstration, what Jane Fonda did for me by taking me aside and having me over to her house for dinner, she had a conversation

she didn't have to have with me. She took time out of her day. She demonstrated to me what sisterhood is, what it means. And because of that conversation, not only was I able to apply it to my life, I had started therapy at that point in my life, thank God, so that I wasn't defensive. When she said, you acted badly, you were badly behaved.

I wasn't defensive. I know defensiveness means you are what anyone's saying. Why would you be defensive if it's not true? It's like what we were just talking about. And for me, it was larger than life in the sense that I, Jane Fonda is somebody I admire probably more than anyone in my life, like Maria Shriver, Jane Fonda. There are a few women that are up there in that realm

of life experience and dignified behavior and that are willing to share their experience. And so for me, it was kind of a blueprint of how I wanted to go through my own life and how I wanted to behave with other women and to tell the women the truth when it's hard to do it. And when maybe you don't like them, but to remember that you're a sister to them.

Well, that's interesting. Like, it's not a pie. Even people you don't like. Yeah, like you don't have to, like even if, it's just sisterhood. It's the decent and the right thing to do is to tell someone when they're slipping and to herald somebody when they're not.

You don't have to be best friends with everybody, but you have to be a sister. Oh, that's interesting. But you think that's a specifically female thing, like men don't have that thing. I don't know what men are doing. I can only speak for myself. I demand you speak on behalf of all men.

I wish I cared enough to think about what men were thinking and doing, but I have enough with my own, like I have to think about being a woman because that is who I am. And that's what I do think about. Yeah. Like there are so many times where I'm like, oh, that girl who I am. And that's what I do think about. Like there are so many times where I'm like, oh, that girl is just annoying.

I don't wanna deal with her. And then I'm like, okay, no. Like, is there any way for you to really help? And is that constructive or is it gonna hurt her? Are you helpful? Is there a way to be helpful in this situation without being hurtful? Like, and I think a lot of the women around me would say the same thing about themselves. helpful in this situation without being hurtful.

And I think a lot of the women around me would say the same thing about themselves. Like it attracts the same kind of, and it's important to remember you don't have to be best friends with everybody. Yeah. Well, it's like a tough love thing, which I'm sure over the years you've run into people who do not want tough love, right? Yeah. Yes, definitely.

It is unwelcome to many, many people. I've had bad versions of that before. Where you give tough love to someone and they're just in denial about it and you go, all right. Yes, absolutely. I don't know what to say. I've been that person. I've been given tough love and not received it.

So I understand that as well. Yeah. It's interesting reading your book because since I met you, probably about 20 years ago, you were a success. But then in the book, it's interesting is that you talk about this story from, I think, Montreal, where you did, you do new faces and like bombed.

Yeah, yeah, bombed. And then to the point where Zach Galifianakis was like, well, goingus was like, was like, good luck. Good luck and good night. That was a tough set, good luck. And I just love this story because you go, everyone from the industry was in the audience,

except one person and you went back to Los Angeles and invited that one person to come see you to a set. And it's like such a tenacity, because it's like that's the perfect answer. I feel like, and you were young to have that, right? Like did you always have a good intuition like that? I just don't think I could do anything else.

I'm pretty useless when it comes to almost anything. I can't even, like I'm not, I can't even say the things that I can't do because it's too embarrassing. You know what I mean? Like I can't, I can't do anything domestic. Like there's nothing I, now I can make eggs and I can scramble eggs.

Okay, I can do that. On a great day. Okay, I can't boil an egg that's gonna come out the way anyone wants it. Okay. I'm not good at cleaning. You launder your sheets? I don't do that.

Okay. I don't do that, no. I'm not good at anything. Do you park your own car? Yeah. Okay, that's good. I can drive. Okay, that's good.

I'm driving. I'm not interested in, I'm a creative. Like that is the way my brain works. Like I can't, I'm not good at- Can you mow your lawn? No, I'm not mowing a lawn. Can you? I don't like the direction this conversation is headed

only because I'm totally happy to have it in real life only because it makes me sound completely off my rocker. But I just want to say, what we'll do is we'll continue this but with this caveat. I've been like this since I was born. This isn't because I have success or fame or money. I've always been not interested in the details and the logistics and the minutia.

Of existence. I'm not interested. I like reading, I like writing, and I like arithmetic. No, I... I don't like arithmetic. No, I relate to that. No, the reason I bring it up is I relate to that. I'm like, I had this in school.

It's like, I was terrible, barely got my diploma in high school because I hadn't done the science requirement and I was basically getting a D in chemistry, which was the sophomore. So it was me and I was a senior and I was like student government, like whatever. And then meanwhile with a bunch of sophomores and they're watching me like barely barely I'd get a D in chemistry today. I would, I would. Yes, totally. With bombas. I would, I would. With bombas. I would, I would. With bombas.

I would, I would. With bombas. I would, I would. With bombas. I would, I would. With bombas. I would, I would. With bombas.

I would, I would. With bombas. I would, I would. With bombas. I would, I would. With bombas. I would, I would. With bombas.

I would, I would. With bombas. I would, I would. With bombas. I would, I would. With bombas. You took a six year break from standup after Chelsea Lately. Big mistake. Really? Yeah.

Oh, I thought you were going to say that it was great idea. No, I now I think about that and I'm like, wow, it would have been better to just keep the ball rolling and get my shit together. In those six years, I got my shit together in a huge way, but I didn't need to take that long of a break and it affected, I had to regrow my audience. And so I wish I hadn't done that.

Yeah. But, but nothing. But nothing. I've been off since my special for about three months. Oh, well, that's nothing. It's not bad. No. But it is interesting,

because I think you do experience feelings. Well, you have to have a life also. You have to have a life. You have to have a life. Like you have to experience life. And I think the thing with comedians that I have definitely seen is that it can be all consuming. That's not how it is for me.

It does not consume me. I do not need to be on stage. I'm perfectly happy off stage and I'm happy on stage. Now I have such an equilibrium about it that I'm sharper and smarter and calmer than I've ever been in my life when I'm on stage. But the time off is as important as the time on. Yeah, I think it is important.

It really is. You have to absorb things to talk about. One of our slow round questions is, like, what do you feel like you didn't know 10 years ago that you know today? That when people say breathe, you should breathe. You should breathe. That's interesting.

Like when people say, just take a breath or don't send that email or wait, that stuff is so true. Like you don't have to be reactive. It's so much more grounded to take a beat and think and be on your feet and be grounded than to be reactive. Then you're not being real and you're heightened. There's never been a time where I've taken a night where I've been upset about something and woken up the next morning and not been less upset.

Right. That's such a great one. What's the best piece of advice that you've been given, that you used? That it doesn't matter how many people say no to you. You just need one person to say yes. Yeah. And that's that Grace Wu story and that Montreal Comedy Festival. But not only that, you know, you get to a place in your career where you think things are going to be easier for you

or you're going to be more respected or all of the areas that you dream about becoming. And you're just going to face different challenges at different points in your life because all of those things can be true while you face the same challenges. And the challenge really is to understand that rejection usually most oftentimes is not personal.

You know, even a breakup usually isn't that personal. Like of a love affair. Totally. That can be very personal, but if you're looking at the grand scheme of things, nothing is really personal. It's the wrong time at the wrong place and it's the wrong person.

Every rejection is an avenue for you to succeed. So I wish I had known, like the greatest thing about aging, like I'm 50 years old and I remember being 40 and freaked out about being 40. And I'm 50 and I'm so happy because I'm so smart and I'm so wise. Like you're not gonna rock me now.

Like I got it. It's yeah, sometimes I go through some tough things, but I know I have enough data to know that I'm gonna get myself out of almost any tricky situation and that my life has been pretty great. So I'm not gonna get upset about this little infraction or if this didn't go well or that person said no or they didn't buy my show or blah, blah, blah, blah, blah.

Like I'm me, I've got it and I believe in it. And that's all you need is you. Like it's the same goes for you. All of your success to this point isn't because of people doing favors. It's because you're consistently good at what you do. So any little thing that isn't at the level that you want it to be is a great opportunity for you to be like,

to respond well to that instead of to crumble and go, what am I gonna do? How could this happen? It's like, oh, whoopsie doodle, that didn't go well. What's next? For everyone, not everyone in entertainment. I mean, not only entertainment, for everyone in entertainment. I mean, not only entertainment. For everyone in any arena, like get better at being you.

Who's someone who you said yes to, who a lot of people said no to? Oh, well, I mean, in Chelsea lately days, almost everybody was rejected. Right, like all the panelists. That was my criteria. It was like, if somebody said no to that, I'll take you. Like I wanted misfits,

I wanted the people that nobody liked. I was like, come here, I'll create a family. Like, this isn't gonna be just about me. This is gonna be about everybody on the round table. Like that was an opportunity for me to have my own show. And I decided that I wanted to share that with as many comedians as possible and with Chewy. Yeah.

And then you take what we were talking about earlier, and I'm not saying this to pat myself on the back, I'm just saying the nature of who you are, it comes through in everything that you do. Like being a comedian, you're getting on stage with a microphone and no one else is allowed to talk but you, theoretically. So to put four comedians on a round table and to force everyone to listen to each other

and know when to get their jokes in, like that is a very kind of nuanced art. You have to listen. You can't just insert yourself because if you didn't listen, you can't just insert yourself because if you didn't listen, you weren't coming back either. You had to be good, laugh, listen, and know when to go in and do your thing.

And that's arguably four narcissists sitting together, listening to each other. And to me, I was able to create that vibe. Yeah. Who are you jealous of? Who am I jealous of? That's a great question. And then the next question is,

who are you jealous of that you thought of but didn't say? Who am I jealous of? I don't know if jealous would be the right word, but I would say, I'm invidious of men as a whole. I would say I'm invidious of men as a whole. Sure. Being able to be the way that I am and not get the same reaction that a woman gets for being like a man.

Say more about that. The repudiation or the, like when men don't like a woman like me, they'll be like, she's too obnoxious or she's so loud or she's so crass. Sure, I can be all of those things, but I'm so much more than that. And so many powerful men have been turned off by me. Yeah.

And that makes me, I guess, more disappointed in men. And I'm so envious that men get to act like me and get away with it When I still have to kind of explain myself, right? And most people would say you don't have to explain yourself, but I still feel Like I have to explain myself to men. That's interesting. Yeah Is there a group growing up that wouldn't let you in? Oh yeah. Really? Yeah.

All my life, I would be the popular girl and then I'd be dumped. Interesting. I'd get kicked out of the in crowd. That's my personality though, because I don't kiss ass. Right. So I get to be top dog and then anytime there's like a power shift or a power dynamic, I'm not like that.

I won't kiss ass. Right, you're not like rank and file anything. No, never. You're just like your own. I'd rather be alone and do my own thing. And you've always had that since you were a kid. Yeah, but as a kid, I took that personally. As an adult, I don't take it personally.

That makes sense. I'm not gonna be your, like- The toady. I'm not to be a part of like, you know, a bridesmaid. That's not my bag in life. Yeah. I'm not in a coterie. I'm not like, oh, like, what's the word I'm thinking of? Like a first, like a first, like a handmade almost to other women. I'm definitely getting that from you. I know. like a first, like a handmade almost to other women.

I'm definitely getting that from you. I know. I can't kiss ass and I really won't. No, it seems. I think it's beneath every, and I don't want my ass kissed either by the way. It seems like it's worked for you. Yeah, I mean, yeah.

It's a good example of it working. Yeah, I mean, there are plenty of times where I've been told I should have done it, but I can't do it. Right. I can, there are plenty of times where I've been told I should have done it, but I can't do it. Right. I cannot, no lo puedo hacer. Can you remember a roommate you had that was particularly bad or good?

I had a roommate I slept with, his name was Jim Bo. I'm sure that he'll, he probably listens to this podcast actually. Yeah. Yeah. He was a good roommate. I lived with him and his brother. And as soon as I slept with him, I was like, this is a disaster. Oh, interesting.

Because then, you know, he didn't understand it was casual. Or he did and he pretended he was okay with it. And then that got dicey. And then my sister goes, can you just not live with men? Because you're going to end up sleeping with them. And I was like, okay. And from then on, I lived with women. Oh, that's interesting.

Because you think that there might be just kind of an animalistic sexual thing. Laziness when you get home late at night and you're drunk and as in my 20s, and you're like, all right, if you're gonna try five times, I'll just have sex with you. Like, I feel bad. You know? I feel bad. I'm not precious about sex or anything, really.

Like, I'm like, let me throw this guy a bone, you know? Poor guy. I felt bad for him. Sure. And I was like, oh, and then, you know, like, it's so easy as a woman to get the ick from a guy. Yeah. You're like, okay, that was just a nice thing for me to do.

Don't get carried away. Right. Like, it's not happening more than that time. What did you get? Do you remember where you got the ick from? Just him in general. Interesting. Yeah, it's easy as a woman to get icked out by guys. What's the smallest thing you've ever been icked by?

Sandals. Sure. Sandals or... What is, unsanitary sandals? Chewing food. Chewing food, like loudly? Open mouth. Open mouth chewing.

Food moving around. I can see that. That's pretty ick. Food moving around. I can see that. That's pretty ick. Food moving around? Like if you can see someone chewing on their food or someone's talking while they have a sandwich in their mouth. Okay.

That's pretty gross. Yeah. Feet. Oh, anything with feet. Yeah, bad clothing. Oh, bad clothing. Hair, hair like in their ears or like, you know, like bad hygiene, dental hygiene is very, it's pretty gross.

I feel like when you're in a relationship, you have to come out with these at the front. I don't think. I think you should tell them. I don't think any man should date me. I mean, I want to be very clear. It's not easy and I don't recommend it. I would advise anyone who's interested

to just look at it from a very casual perspective. I'm totally into casual sex, but I do not want somebody in my bed on a regular basis. I like to be alone. Yeah, so you're good with that. Yeah, and I'm very into casual dalliances and I invite those and I welcome those, but you have to come into it with the same spirit

that I'm talking about. That's interesting. But did you have... I'm guessing you've had a bunch of Jimbo-esque relationships through the years that where people are like, -"No, no, this is a relationship." -"Yes." And what... Are you just super frank in those situations? Have you had to learn to get better at sort of getting ahead of it and saying, like, that's not what this is?

Like, do you feel like you've learned the hard way of like being upfront about it? I mean, I think like, you know, like with Joe Coy is a good example. Like I went into that relationship in the spirit of like, I meant it. I wouldn't do anything I didn't mean. I'm not for sale in that way.

Like he was such, you know him. He's such a great guy. Yeah, he's just sweet. And he lights you up, you know? And he's such a cheerleader. And I met him at a time in my life where I was kind of ambivalent. I was ambivalent about life and my career.

And I was just like, what's the point of everything? It was kind of around COVID. And I just kind of started to become very introverted and not, and I would just felt like this malaise. And I really, and he kind of scooped me up in a way. And I really went into intentionally, I thought, what a nice surprise this is. And then once we were in the relationship,

it was like he had never met me before. Sure, yeah, that happens. I've seen that happen. And I was like, whoa, whoa, whoa, whoa. What did you think? Like, you've known me for 20 years. Right. This is too much.

Right. And it's like, you got to give me some room. Right. There's no space. Right. And, and, and there's nothing he did that was mean, spirited or bad, but it was like, you're, you're acting like you've never heard a thing I've said. And so that becomes confusing, I think, for people,

because they think, well, this is different. And it's like, well, yes, this is different, but I'm still who I am. And I'm not subscribing to this way of life. Like, I can give you all I can give you, but I can't give you me. I mean, that's a hard thing about relationships. It's like, I feel like you have to keep relearning

the same thing that you're describing over and over again, which is like, that's who this person is, and that's who you are, and you're like an extremely specific person. You go with your gut all the time, you shoot from the hip. You're like an extremely specific person. You go with your gut all the time. You shoot from the hip. And I like romance and I like sex and I like men,

but I don't get carried away thinking that this is, that you're gonna turn me into something I'm not. Right. Like when I say I'm envious of men, this is a perfect example of why I'm envious of men. Because it's okay for men to feel this way. But when a woman states that this is how she feels, men are confounded.

They're like, she can't be telling the truth. It's like, no, no, no, this is how I feel. Yeah, this is what I want. This is what I want. I want lots of men. I want space. And I want lots of space. I want lack of commitment. And I want respect. I I want lots of space. Yeah, yeah, yeah. I want freedom. I want lack of commitment and I want respect.

Right. I'll respect you too. Right. But let's not get it twisted. We're not starting a family. Yeah. And we're not getting married and we're not going to be together forever. Yeah.

That's not what I'm up to. That's not what you're up to. That's not what you're after. No. This is, I don't have much material right now, but I, because I'm square one, you know, because I just did the special. But I wrote this thing recently, which is I love coffee so much, because when you drink it,

you're jacked with energy for like 20 minutes. And if I'm being honest, I think if you enjoy 20 minutes of your day, I think that's enough. I think 30 minutes and you're a Buddha, which is why I feel like heroin could go mainstream. Like you go to a cafe, you're like, two shots of espresso and my wife will have the heroin.

It's been a tough morning. It's a bit of an opioid crisis over at the house, which is kind of a dark time for it. Do you think that is true in some ways? I do. If you enjoy 20 minutes of your whole day? That's how I feel, yeah. Really?

Look, maybe it's an overly pessimistic take, but I do feel like if you have 20 minutes where you're just at peace, that's nice. Ha! I'm considering this. Are you thinking like it's gotta be 20 hours of the day? No, no, no. What's your number?

What's your number on enjoying your day? It's gotta be more than 20 minutes. No, I get it. But I like what you're number on enjoying your day? It's gotta be more than 20 minutes. No, I get it. But I like what you're saying, but it is cynical. I'm being intentionally cynical for the joke. Of course, of course. But I think a lot of people probably would agree with that.

Yeah. I think that's part of why coffee is like an enjoyable ritual. Yeah, I don't drink coffee. Because it's reliable as hell. So funny that you're talking about coffee. Well, it's not that funny, but I mean, the joke is funny. But the subject of coffee, I had a cappuccino today and at my hotel, I never drink coffee.

I just don't drink coffee. I don't like it. It makes me sweat. I'll have a nice coffee once in a while if I'm desperate. But since I was in Europe and I was like, struggling with time zones and everything, I just started just taking shots of espresso at random times during the day.

And coffee is such a fucking thing for people. It is serious. Oh, it's an ordeal. Like people are so into coffee to the point where I'm like, shut up about the coffee. I know. But what you just said elucidated to me why it is such a big deal because it is an escape hatch for people. It is their 20 minutes of the day.

I've got to get my cup of coffee and I've got to have it perfectly. So it is that 20 minutes that people are desperate to have every day. If they don't have it, they'll lose their minds. Yeah, I understand you now. I mean, I understand it from what you just said. That's great.

Yeah. Do you have any new things you're working on that are like half baked? I mean, I'm talking about this story on stage where not for the same reasons, it's not like I'm working out the material, it's the actual basis of the material, which is about me, I love microdosing LSD.

I love LSD. I love microdosing LSD. I love LSD, I love microdosing anything pretty much, but LSD is my personal favorite. And it's not like you hallucinate or anything, it's just like a coffee. Okay. And I have a great story about traveling to New Zealand and Australia with my cousin,

who's a real eye dotter and T-crosser. She's a type A and I'm a type A for about two hours every day and then I'm a type Z. Once I get two hours done, I'm very efficient and then I like to have a good time. And we were checking into New Zealand and she is you know, those custom slips and it's like, do you have vegetables? Do you have alcohol? Do you like, do you have vegetables? Do you have alcohol? Do you have any money? Like asking all the things that you may have brought.

Do you have insects? Do you have any beef? And she checks beef. And we're in New Zealand, we're traveling. We were going there for 14 days. And she checks beef. And I am like, what are you doing? And she goes, I have some chomps meat sticks

in my backpack. And I'm like, that's not doing? What are you, what are you? And she goes, I have some chomps meat sticks in my backpack. Yeah. And I'm like, that's not the beef that they're talking about. That's not what they mean. First of all, that's sealed. That's a fucking beef stick. I have edibles, mushrooms, and LSD, okay? That I'm smuggling into a fucking New Zealand.

And you're sitting here declaring fucking beef jerky? Get the, I was like, fan out. Get the fuck away from me. We are not traveling together. And so my dilemma is talking about this on stage is a basis for, you know, arrest. Like I can't be openly talking about transporting drugs all over the world unless I'm willing to stop

transporting drugs all over the world. So it'm willing to stop transporting drugs all over the world. So it's actually a kind of different dilemma. I'm like, oh God, I might have to start traveling with my LSD, stop. Stop traveling with your LSD. Or I don't get to do this material. So it's a conundrum. That is so funny.

I think, my feeling is, it's a funny, it's a great bit. You should definitely do this a bit. You can definitely continue to travel with drugs. What are the odds that the customs person is going to be know you're special? But I, my, no, no, no, no. About drugs and even remember it? My fear is that I will be on some list at some point.

A list, okay, a list. Because of our administration. Right. Or because I'm so vocal about it. You'll be on an on some list at some point because of our administration, or because I'm so vocal about it. Like it's basically like dangling a carrot in front of a rabbit going, I think, ha ha ha ha ha, here's the, I'm doing this, but I'm not doing this. But I mean, I've also been talking about this my whole life.

I'm very public about my drug use. And if anything, people at TSA are kind of helpful. They'll be them mushrooms. I mean, I'm very generous with my drugs. We've discussed this earlier. But yeah, so that's my different sort of dilemma. That's a great bit. That's a great story. So I feel like I have to share it. Oh, you have to tell that.

And then, but honestly, even if you got arrested, it's like, you know, you're not gonna get away with it. You're not gonna get away with it. You're not gonna get away with it. You're not gonna get away with it. You're not gonna get away with it. You're not gonna get away with it. You're not gonna get away with it. You're not gonna get away with it. You're not gonna get away with it. You're not gonna a great story, so I feel like I have to share it.

Oh, you have to tell that. But honestly, even if you got arrested, it's like, and that's a story too. Yeah, that's right. But you don't want to get arrested in the wrong places. No, I know. Like, I'm not going to take my LSD to Dubai. But also, nobody even knows how to look for LSD.

Also, I wouldn't do that anyway. Yeah, no, I wouldn't either. You know what I mean? But I would, kind of. I kind of would. But there's certain places where I would not mess with. Iraq. Yeah, I would not mess with certain drug laws.

Or Iran, right, right. That's right. That is not something, I mean, you're good in Spain, right? Right. You'll be fine. What I can do is just mail my drugs to wherever I'm going. But even saying that.

Yeah, but I'm not going to be mailing them from my house to, you know, they're going to say, from Chelsea Handler to Chelsea Handler. I'm learning so much in this interview. Yeah. And then the final thing we do is working it out for a cause. If there's a nonprofit that you like to give to, we will contribute and link to them in the show notes. That's nice.

You know what nonprofit I like is the Carter Center. The Carter Center. Yeah, in Atlanta. That's Jimmy Carter's foundation. Jimmy Carter's organization, that's great. Well, we will contribute to them. We'll link to them in the show notes. Chelsea, you're a riot.

Your special's a riot. Your book's a riot. I think you are a gift to the earth and I thank you for coming to the podcast. Thank, thank you, Mike. Thank you. So much fun. -♪ Working it out, cause it's not done. We're working it out, cause there's no... That's gonna do it for another episode of Working It Out. You can follow Chelsea Handler on Instagram,

at Chelsea Handler. Her book, I'll Have What She's Having, is on sale now at your local bookstore. You can get tickets for all of her tour dates on ChelseaHandler. Her book, I'll Have What She's Having, is on sale now at your local bookstore. You can get tickets for all of her tour dates on ChelseaHandler.com. The full video of this episode is on my YouTube channel, at Mike Birbiglia. Make sure you click subscribe.

We're posting more and more specific videos over there. We're working on a little mini documentary about the creation of a good life, and that's gonna pop up soon. Check out birbigs.com to sign up for the mailing list and be the first to know about my upcoming shows. Our producers of Working It Out are myself, along with Peter Salomon, Joseph Verbigli, and Mabel Lewis.

Associate producer, Gary Simons. Sound mix by Ben Cruz. Supervising engineer, Kate Belinsky. Special thanks to Jack Antonoff and Bleachers for their music. As always, special thanks to my wife, the poet J. Hope Stein, and our daughter, Una, who built the original radio fort made of pillows.

Thanks most of all to you who are listening. If you enjoy the show, rate us and review us on Apple Podcasts, that really helps. We've been doing the podcast for five years, over 170 episodes, all free, no paywall. Go on and say what your favorite episode is on Apple Podcasts, it'll help new listeners find their way through all these episodes. Thanks most of all to you who are listening.

Tell your friends, tell your enemies, tell the TSA agents. Always good to lighten the mood. They're giving you the wand sweep and you go, hey, I hope that thing doesn't detect great podcasts because if it did, you'd find one hosted by Mike Birbiglia where he talks to other comedians and creatives about the creative process and sometimes they give each other tags. But if it does, it's gonna start beeping. Thanks, everybody. We're working it out. We'll see you next time.