I’ll Have What Chelsea Handler is Having

Published Feb 25, 2025, 8:00 AM

Happy 50th birthday to Chelsea Handler! We’re honored to host her on her big day and to celebrate her new book, I'll Have What She's Having. Fortunately for us, nothing is off-limits. Katie and Chelsea take on her evolving (and often hilarious) approach to love, sex, and breakups. Chelsea spills on the hard lemonade empire she built as an eight-year-old, her infamous Cuomo crush (yes, those nipples), and why she refuses to be tied down—literally or figuratively. Plus, she and Katie hash out an old grudge, talk psychedelics, and discuss why women need to double down on sisterhood in tough times. Raunchy, raw, and ridiculously funny, this episode is Chelsea at her best.

Hi, everyone, I'm Katie Couric and this is next question. I first got to know Chelsea Handler a number of years ago when I was anchoring the CBS Evening News and our team invited her to the White House Correspondence dinner. Needless to say, we had a blast and we have been friendly ever since. I would say friends, but I don't see her that often, but when I do, I'm always really happy. So I was thrilled when she told me she would do an interview for this podcast all about her new book called I'll Have What. She's having kind of a riff on when hearing met Sally. Of course, obviously, Chelsea is really really funny, but she's also very thoughtful and a very good writer. Her writing, in fact, is full of heart. So we had a fun conversation and talked about everything under the sun. I hope you enjoy listening to it as much as I enjoyed having it. Here's Chelsea Handler. Hi, Hi, how are you going? You look great. I was just watching you with Sophia Bush. I'm like, hey, Chelsea, don't do everyone before you do me.

Oh my gosh, I know so many podcasts now, It's like, you should see.

The list of podcasts. I think we can start, because I know you've got a million things and I know what this is like. But first of all, Chelsea, I loved your book. Thank you, Katie, thank you so much. It's music to your ears. I know when somebody says that, because as someone else who's written one book, not eighty seven like you have, it's always nice that someone actually read the book, loved the book and tells you that, right, I mean, do you need that kind of affirmation after all these years and all these books, because I know I did when I wrote mine.

Yes, it's always nice to hear that someone enjoyed something that you wrote.

Absolutely. I loved to hear that. I don't depend on it, you know, because that's a slippery slope as well.

That's true, that's true.

If you hang your hat on that, then you hang your hat on the good and the bad.

So I like to just kind of be in.

A neutral zone where I don't need a lot of affirmation, but it's always very welcome to get it.

Yes, well, it was so much fun reading it. Before we kind of dig in, I wanted to ask you how you're surviving this really actually pretty devastating and terrifying time. You know, I don't want to be a Debbie Downer or anything, but do you find yourself, Chelsea, kind of reading the news NonStop and waiting for the next crazy thing that the president or his sidekick Elon Musk does.

Yeah, it's pretty upsetting and alarming and revolting.

All of those things.

I'm trying to I've been in Whistler for a little bit.

I'm about to come back and do my press and and I am just thinking of the ways that I can double down on my love and my kindness and my empathy to be even more compassionate and generous with my time and resources for all of the people who feel so scared and fearful. You know, I'm in that group, but obviously not as an immediate threat to my life. I don't know what to say about everything that we're reading and experiencing. And I and I my one thing when we came into this administration was like, I'm not letting them steal my joy again, Like you're not going to steal my four years of like you made me.

So angry and you know, ugly and anxious. Yeah, and so here we are again.

But I'm like Okay, Well, all you can ever really choose is how you respond to a situation. And I'm going to choose to be calm and to be and double down on all the good stuff and do what I can do within the people that I come into contact with in my communities, you know, and obviously be there for the bigger actions when they're necessary, and we have like an idea, yeah, what to do.

But right now it's pretty it's pretty disheartening.

Yeah, so many people, I know, Chelsea, are feeling so hopeless and powerless. And you know, I'm curious because I do think focusing on the people who are most vulnerable and doing what you can to support them and encourage them is a great outlet. But I'm curious when you say that, what kind of people are you talking about? Like, when you envision helping certain people, are you talking about the LGBTQ community. Are you talking about.

I'm talking about any community that's being targeted by this administration, which is you know, the trans community, any person of color, really, I mean, the all women are threatened by this. I'm talking about just kind of extending love and like gratitude and all of the good stuff because we're faced with such a dark situation, So what requires us to dig even deeper for the light and to actually remind each other about the power of togetherness.

Like for me in my.

Life lifetime, this is the first time where it really feels like women understand the importance of having each other's back and of working together. The whole reason we're in this political atmosphere is because of the threat that men feel from women because we are so powerful, because we are not going anywhere, because we've discovered that we don't our only value doesn't come from being a mother or a wife, that we have value and multitude of other ways. Like that's why men are so scared and freaking out and acting like this, because they're like, oh, here they come, and they're right, we're coming.

So I have to hold on to that, And that is very much the.

Essence of what I'm talking about in my book is about reminding each other of how powerful each of us are and to be a sister to every single person that you can be a sister to, especially when the backdrop is so odious.

I couldn't agree more. On the other hand, there are a lot of sisters who are supporting what's happening in this country, which I find mind boggling and really discouraging. And you know, it's really not a unified front when it comes to women in America.

No, and it never has been. But that's we were you know that that's going to take time too. We were poisoned by men to you know, like it's a zero as sum game between women.

So we've believed that women are a threat to each other too.

But now I feel like at least we're coming out of that haze, while there's still some remaining women who haven't gotten a memo. I believe in women, like I think women are going to be the ones that save the day.

And I also think there are some really great men out there. You know, I hate when we kind of make these rash generalizations like all men and even the patriarchy. Yes, our society was founded on patriarchal principles, but I also feel like there are so many men out there who don't want to turn the clock back, Chelsea, who appreciate us and what we contribute. At least that's my experience. Absolutely. Yes, of course, there's.

You know, there are men that are incredible and totally get it, and those are the men that I respect and can have sex with because I can be attracted to them because this other thing is just a it's such a talk about an ick like I mean, you know, so anyway, that's my choice. I feel like optimism is a choice, and the darker things get, the lighter.

We have to become. Let's be like together, Chelsea Handler, because I am right there with you. Well, let's talk about this book because we're here to do that and to let everybody know what this book is about. It's called I'll have what She's having. It's your seventh book, not your eighty seventh book. I was trying to be funny, but you know, as I mentioned, I wrote a memoir and almost put me in my grave. So what is with you and writing books? You obviously love it. The dedication is to all the flight attendants because you write primarily on planes. I'm just curious about your writing process a little bit, Chelsea, sort of how you come up with the idea, the genesis of that, How do you kind of process each of these books, how you pick the topic. Can you give me some sort of insight on that?

Well, this book, for instance, came around when I was dating Joe Cooy and I was very publicly in love and we were demonstrative about it, and everyone was eating it up and people were happy for us and cheering us on. And I had never been in like a public relationship where that kind of support was so sweet. I thought, oh my god, everyone's rooting for us, and I was, of course rooting for us as well.

And so the book was an editor had. My editor had asked if.

I want to write a book about falling in love like Chelsea Handler falls in Love, and I said sure, I would love that, and then we broke up.

So I was like, WHOA. I was going to say, you loved it when you were in love and then.

And then I'm like, well, I guess I can't write that book now. And then she was like, well, what about the breakup aspect? Because I was handling the breakup in a much different way than I had in previous relationships. And I thought, I don't know that sounds like a want want to a breakup book.

That's so not me.

And then I just said, let me just sit on it for a few months and see if anything drums up in me that wants to needs an outlet, and I've never really been wanted to do something for you know, I usually do it in the opposite, you know, and if not for hire, it's like, I have the idea, let me tell you what I want to do.

So now I was like, okay, I had to come up with an idea, but I didn't want to force it.

And then I just thought, what do I have to say, Like as a woman as I'm turning fifty, as I have grown up in this world and especially the last like ten years, and how much different I've become, and like the evolution of a person who's constantly searching to find more meaning and more purpose and understand what your purpose is here, and like to use your good talents for good and kind of keep.

The bad stuff to a dull roar if you can.

And my kind of vision as a little girl, of the kind of woman that I wanted to become. I think we all kind of lose sight of what we thought when we were kids. I remember envisioning this woman that I would be. You know, I wanted to be brave and fierce and independent, and I wanted to stand up for things. And so when I really sat and thought about, like where my life began and what I've done with it with I thought, oh, what a kind of nice guide for women to check in with themselves and be questioning am I on the right track?

Am I on the right track that I want for myself? Or am I on a track someone else.

Put me on? Yeah? I really liked it with stories about, you know, different experiences. But in a way it is like a self help book. You know, I found myself reading it and wondering about my own life. So I think it's great in that way. And it's also very funny. It's very breezy, you know, it's fun to read because you feel like you're just kind of shooting the shit with Chelsea Handler. But it also is very thoughtful and full of heart. And I want to ask you about kind of your memories as a little girl, because you've written about your childhood before Chelsea and a lot of books that you've written, But there was one very funny story about your lemonade stand, and it's clear that you were this ball busting, precocious, little ambitious tyke from a very early age. So tell us about this lemonade stand, how you were able to maneuver You were so very funny and calculating at a very early age. And not only do I want to know about that story, but where you got this from? But first tell us about the lemonade stand.

Well, the lemonade stand. I, first of all, I needed to start making money because my parents did not have a trust fund for me or a dowry. I inquired about that as well, and I realized pretty quickly that I was going to have to make my own way, that my family was not going to help me. And there were a lot of kids, as your mom explained to you, absolutely there were six children and there were so that was annoying as well. When I came home from the hospital, I was like, why are there so many other kids here?

How many kids do you guys have?

It just seemed so irresponsible, the whole dynamic, right, My parents weren't parents, they were just kind of like other people that were in the.

House, baby makers.

Yeah, So I started a lemonade stand and then I did that for one day and realized they're right.

And how old were you and who was your partner at the beginning? First I was eight.

I did a regular straight up lemonade stand, and I made about three or four dollars, and I thought, well, this is a complete waste of my time. And then I thought, oh, you know what I need to do is put a spin on the lemonade stand and turn it into a hard lemonade stand.

Well first, so wait, wait, wait, because first it was with your sister and she demanded fifty percent, and you were like, I don't want to give away fifty percent, right right? So you found this kid named Nelson in your neighborhood.

Well, first I decided I wanted to do the hard lemonade stand, Katie, and then I enlisted my sister and that it was the hard lemonade stand was with your sister, yes, So then I enlisted my sister. I didn't like the overhead that required me to pay her because she wanted it to be fifty to fifty, so I had to let her go after one of the like a couple of first couple of days on the sidewalk, I was like, here, so we're.

Not eight, eight or nine? How old are you eight? I was going to say eight o'clock and then I then I.

Decided to get cheaper labor, so I went and hired another eight or ten year old boy named Nelson. And at the end of the first I think it was like ten days it was. We went it was bonkers. Our lemonade business went through the roof in Edgar town Mark's vineyard. That we made like three hundred and fifty nine dollars in the first week or ten days. And I gave Nelson his commission, which was three dollars and fifty nine cents, and he was he thought he had hit the jackpot.

He could not believe his good fortune. But Chelsea, where did you get the liquor to make the hard limonade? Come on from my parents' house. You just stole it. Yeah, they're not drinkers.

I don't even know why they had alcohol. They never drank. I'm a first generation drinker in my family. I wear that as a badge of honor.

So proud. Yes, thank anyway, So you're making a boatload of money and you ended up like, hey, I like making my own money. This is really great. But so where did you get this ambition? Do you think it's because I remember reading or talking to you about your parents how you used to get yourself up to go to school in the morning while they were sleeping. So wasn't that early need for you to be independent and a hustler. Did that lead to this ambition or do you think you're just kind of hardwired this way? I think I don't know.

I'm sure it's a combination of your surroundings.

And your nature you know that you're born with.

But I'm definitely a hustler and I think that's great. I mean, you're a hustler too. I think it's important to also. I mean, I wanted a big, loud, brave life.

That's what I wanted.

I wanted it to be like I'm like, I have to get to LA so I can become famous and then people will start to understand that I have something to contribute. Like I had no idea where my confidence came from, but I really believed in myself and I just thought, Okay, this is how it's going to be like And when I look back and think about all of these things that have come true and the fact that I am.

This person, it's really empowering.

And it's such a nice idea for all women to do, you know, to check in and make sure that you're because it's like the essence of who we are as children is so clear and then the world kind of shits on us and we get our hearts broken, and things happen, and we become kind of we sometimes can get away from ourselves and who the essence of who we are is. So it's really nice to think about the things and the things you did as a kid, you know, and to be like, oh, that's who I really am.

In fact, one of the quotes you include is, when we are children, the essence of who we are as front and center. We are unscathed by what can very often be an ugly world. Bringing that child into adulthood, even only for moments at a time, is how we remain true to ourselves, hold on to that child tightly as if she were your own, but because she is. I mean, a lot of this book really is on the evolution of Chelsea Handler, if you will, kind of what you were like in your twenties and thirties and kind of how you've changed in your forties, but also how you've gone back and retrieved that essence of who you were as a child. Is that a fair assessment? Definitely? I love that. Yes. And it's also about therapy and how therapy kind of helped you do that, right, Chelsea, how therapy gives you the gift of a self awareness. We all could use a little bit more of that, and more compassion, more.

Empathy, and more of you know, it takes a lot of grit to go through therapy. It takes a lot of grit to face an ugly situation. But at the end of it, when you come out of it, you're kind of able to deal with more difficult situations in a calmer, more loving way. Not every conflict doesn't have to be an explosion.

Is this called cognitive behavioral therapy, Chelsea.

It is also called that, Yes, and that's another term for it, or microdose LSD.

They're all the same. It's all the same, commensurate. I sent my daughter a paragraph because she can be kind of reactive at times, you know, and doesn't have that seven second delay, and you know, kind of lashes out at times. She's a wonderful person, by the way, but she wrote me back. I texted it to her. She goes, bro that's CBTA, Yes, it is. It is.

Listen, you have to I've read so many self help books and they're all saying everyone is saying the same thing. It's a matter of the use of language that gets you. It's like taking a horse to water.

You know, some things resonate with certain people and some things don't.

But it's also I think you may clear in your book, Chelsea, it's like learning it and then putting into practice. I mean, there's a big bridge between intellectually understanding yourself and actually changing your behavior in real time. Right Yeah, it's the application of all of the knowledge that you glean.

You have to then make it. You can't just know about it. You have to apply it to your life and then change the way that you react in certain situations and the way that you are as a person. You know, and for me, I was so such a high viber and life of the party type of personality that I started to that started to become my identity.

So to kind of dial that back and kind of be a little.

Bit less fun and less and almost boring to some people, you know. The contrast that was a little weird too, and awkward because people are like, where's Chelsea? Like we want the real Chelsea. I'm like, well, I don't know who she is anymore. I'm having a transition right now. Try to take all the good parts of my personality and apply them to this new, better version of myself.

If you will. If you want to get smarter every morning with a breakdown of the news and fascinating takes on health and wellness and pop culture, sign up for our daily newsletter, Wake Up Call by going to Katiecouric dot com. Did you ultimately feel like you found balance? Because I know that you were very kind of introspective and you stopped being the life of the party and everyone was like, as you just mentioned, what the hell is wrong with you? You know, bring our friend back? And were you able to kind of put the fun Chelsea together with the more thoughtful Chelsea or the more listening Chelsea ultimately, Because I don't know that's hard to do, right.

Yes, But I think first of all, it kind of happens naturally and organically because it's very I think it's.

Similar to going to school all year.

You go to school for nine months out of the year, and then you have the summer, which is three months to kind of absorb everything you learned over the school year.

While you're not learning, you know, you let it sink in. So I think that's analogous to therapy.

It takes time to sink in and while it was many moments of severe disco or ugliness or you know, self loathing or whatever comes along with really taking a good look at yourself, the end result is you become more solid and more grounded than you ever were.

You become like a tree. You're like, okay, I've been through this. I'm not a leaf. I'm the tree actually, And that's how you start to go through the world. And then you're a little.

Bit more unshakable, so you're even stronger than you were before.

I'm thinking about all the people who can't afford therapy, you know, Chelsea, And I think, is there is there something you learned or something that people can do to get more centered and kind of to become a tree instead of a leaf? And what was the most important thing I think in the whole process that you learned.

I think it ordered for us to be a little bit more on solid ground.

We really have to practice, you know, being proud of ourselves, being like happy about where we are, thinking about all the things that we're grateful for, and these things and sound corny when you don't really practice them, like oh, I'm going to write a gratitude journal. No, I'm not going to write a gratitude journal, but I Am going to get up every morning and sit write down ten things that I'm grateful for.

Whether it's my house, my friends, my shirt, my hair, whatever.

Just stay it, be grateful. It creates gratitude around you, and it creates abundance. Like all of these things are true. I've been down the road with everything, so I wouldn't be talking about it unless it was authentically.

The stuff that I do. And I can can see the change.

And I think in order to really be grounded, you have to know and understand and respect yourself, Like you have to have the confidence of your convictions and.

Know that wherever you are in life, you're the reason that you're here.

You got yourself this far, and it's it's very likely that you're going to get yourself a lot farther, just based on the fact that you got yourself this far. So like there's data, you know, we're providing data for ourselves, So that's you should have in confidence and then be instilling yourself with confidence every day.

I was very interested in reading about confidence in your book because I think when I give talks or people ask me questions, a lot of times it does revolve around confidence, especially for women, and I love that you've had a solid sense of yourself, although it's been tested at times in your life too. But I wanted to read a couple of paragraphs because I really liked them. When you got fired from your job as a receptionist at a law firm, right, and you write, I didn't care that he called me stupid. Some lawyer had called and said, when can we fire the blomb bimbo? That's the receptionist, right, And it was you he was asking me, Right, So you said I didn't care that he called me stupid. I knew I wasn't stupid. I've been called stupid many times in my life. I've been called dumb, obnoxious, trashy, raunchy, crasts, a fake, and various other things throughout my career. I've been all of those things at certain moments, but not one of those words in cup who I Am. If this had happened on a different day, I would have walked out of that law office in tears. None of that happened because he caught me on a day where I felt good about myself, hopeful about the future, even though my life was anything but stable in that moment, I was my true self that day, and I was grounded in that idea that I would set out to do what I came to California to do, to make a living at being me and the grand scheme of things. This man didn't matter at all. He serves as a reminder to me on the days when I do not feel strong, confident, or hopeful, to tap into the version of me who does, to know that every feeling passes, that no moment in time is permanent, and that the truest version of who we all are is confident, hopeful, and resilient. I just love that because you know, I think you conceive that. Not every day you feel that way, but there is that part of you you can always call on when you're not. Yeah, it's like leaning on someone else's show.

You know, as women what we have to do and extend the kindness we have to extend to each other in the name of sisterhood.

It's like, if you don't.

Have that at your disposal in that moment, lean on your own sisterhood, like you have yourself to lean on, and that's also the strongest shoulder in your life. So really, too, we have to have, you know, the ability to know how valuable we all are, every single one of us.

And it's a good reminder.

Yeah. I just thought it was a great pep talk to yourself and ergo a great pep talk to the reader, and you talk about sisterhood. Jane Fonda, you also write about you all were friends, and you know she had you come over to her house for dinner because she was pissed. It kind of the energy you were admitting at a John Lewis fundraiser, And I thought that was as you talk about that being a true sign of sisterhood, that she would take the I'm an effort to kind of tell you that and be so brutally honest that you were really grateful, and it kind of shook you a little bit, didn't it. Absolutely?

And what she said to me and summoned me over to her house and kind of told me that my behavior was bad and that I had acted badly and offended people, it was pretty mortifying to hear.

Not pretty mortifying, it was mortifying.

I was horrified at myself, and I had just been to therapy for enough time to understand that being defensive is just an admittance of being wrong. You can't be defensive when someone's telling you something about yourself, and if it's not true, then you wouldn't be defensive anyway because it doesn't matter, you know, it's just simply not true. So it was true what she said to me. And through even the mortification of hearing that and being so disappointed in myself and being so horrified that she was disappointed in me, the overarching theme of that moment I remember thinking was like, Wow, she's really being a great, big sister to me. Like that's the kind of sister I'm going to be to some two other women.

And I think people who can be really honest about their feelings, like I wasn't really honest about something that happened between you and me, and it was really not you, but it hurt my feelings, and I wish I had just said to you, Chelsea, it really hurt my feelings that you didn't defend me on your talk show. What happened. Well, I don't know if you remember this, but I had a syndicated talk show. It wasn't a very good fit for me because I'm kind of a news for her, as you know, but you were nice enough to come on the talk show, and at one point I was saying, I was really excited that Jennifer Aniston was getting married, you know, because I really liked her. I was happy for her, and I think I must have said something like, you know, are you going to the wedding? You know, just like what you do on daytime talk shows, right, And then she came on your talk show and you meant it in a nice way, and she said, I thought Katie Kuric didn't Katie kirk used to be a journalist, and I thought it was such a diss and maybe she was trying to be funny or I don't know what, but I felt like you should have defended me and said, but she was really being nice and trying to be really supportive and loving towards you. But you didn't, and it hurt my feelings.

So now i'm oh, oh I did, because I think you did say this to me before. I remember, Yes, I remember you being upset about it, and I remember being surprised. I don't know if you texted or email me, but yes, you definitely did. So, first of all, don't see you did to stand up for yourself and you don't even.

Remember maybe dementia is another one of my problems. We're all we don't worry, we're all going we're head in that direction.

But I'm glad you said it again nevertheless, And yes, I don't think it didn't even cross my mind that she was dissing you in that moment.

I think she really coflecting. Yes, I didn't read it that way at all. No, maybe I'm hyper sensitive about stuff like that.

Well maybe, I mean, maybe not, I don't know. I mean, it was it either way. It's not the you know, it's not like such a big dig.

I know, well kind of if I know, for somebody who's spent her whole career trying to be taken seriously and being really proud, I think. But that's what I mean.

I think everyone does take you seriously, can't correct, so from my lips to your ears, I think you can count on that.

Okay, thank you. I feel much better now. But yes, I feel like even though I texted you, I feel like we had never really talked about it.

So well, thank you for bringing it up and my apologies. I'm sorry.

Yeah, now I understand where you're coming from.

I get it, Okay, Thank you all. Right. Somebody asked me to ask you. You're known for being fearless. What is the one thing that still scares you? Oh? What scares me? Oh? God?

The commitment to any sort of long term commitment, whether it be to a person, or to a job, or to living somewhere.

Like, I like you like freedom. I think you value freedom above everything. Yeah? Yeah, what is it about commitment or about being tied down scares you so much? And I'm sure with therapy did you talk about that? Is that your parents' marriage. I'm trying to figure that out.

I think I don't look at it as a fear of something. I want to be free. I want to be able to fly around the world. I want to be I love a sense of like when something's impromptuo, I love spontaneity. Like I look at it as like I just want to like fly if anything that could prohibit me learning and growing and traveling is like oh, and so yes, I could see.

How it would be a fear. But I think through therapy I learned that it's okay that.

I have these feelings.

It's okay that I don't desire a long term romantic commitment. It's okay. Instead of wondering what's wrong with me. It's like, I want to love you. Yeah, I want a lot of lovers. I want to have a lot of sex with lots of different guys. I want to have lovers in different parts of the world. That's okay for me to say, and that's true. That's how I feel.

And I love loved the section about your COVID crush on Andrew Cuomo. You know, he's running, he's running for mayor Chelsea, so he's probably going to be in the public eye a little bit more. But I mean, you are so funny. You were turned on by Andrew Cuomo during his press conferences during COVID because he seems strong and in charge and telling everyone what to do. And I think a lot of women actually had a crush on Andrew Cuomo during that time. And then you became super obsessed with his nipples. I don't know where I was, but I missed Nipplegate tell me about his nipples. People were so I can't believe I'm asking you to tell me about Andrew Cuomo's nipples. I'm so glad that you are.

He would be in those browarning press conferences, you know, with his crew he had that like, you know, first assistant, that woman who was like this badass and would just yell at everybody. And he had that white those white golf shirts on sometimes you would wear like a shirt, a business shirt, you know, a suit shirt.

But his nipples were always protruding, like they were always very hard.

So then people were speculating on the internet that he may have had nipple piercings. And I knew enough to know that no straight man over sixty has his nipple pierced, you know, white guy, Why why would he do that? So but then when I went to investigate the nipple situation, because I did believe I was going to be penetrated by him, I went and zoomed in on his nipples and realized there was a far worse situation percolating.

He had droopy nipples, his nipples were headed in a southerly direction.

Katie and I had never faced a storm like that before, so that made me rethink everything.

Well, you had a text flirtation with him that lasted some time. You were even planning to rendezvous. He said he was open to dinner at the governor's mansion. You didn't want to date him. You just want wanted to have sex with him, and then the worst possible thing happened. He ghosted me. So sad what happened? To talk about a bullet dodge?

My sister's like, you seem to get out of all these situations just in the nick of time. I think somebody in his office caught wind of him talking to me and realized what a bad look that would be. In the middle of telling everyone to stand six feet apart for me to be like.

And then some of your then your sisters or somebody suggested you guys have sex outside.

And from behind that way, Yeah, double safety with masks on. Yes, yes, of course, Katie. Obviously if you're going to take it from behind, you need a mask. And it never No, it never happened.

This is probably this is probably the I don't know, the most risk a podcast I've ever done. Good.

I'm glad to serve up my purpose. I'm happy, I'm happy to provide that for you. And yes, he ghosted me. I was debit stated because it was in the middle of COVID, so people in COVID who were not in relationships were scared.

I know I was.

I was like, Oh my god, is this it like, are we ever going to be able to interact again?

Like a sex is gonna happen.

So when he came on the scene, it was like a mirage, and I just thought, I'm gonna I have the advantage of being a public person if I put it out there that I want to have sex with him, kill here about it, and then I'll hear from him. And that's exactly what happened, until it didn't happen.

So is it over? Do you think there's a chance this relationship could be I don't know, restarted in some way.

I think it's I think it's seen, it's I think it's over now you do think, I'm sure as soon as he hears all of me telling everybody the story, that will really be the nail in the coffin. But the nail in the coffin was when he was removed from office for being a sexual predator.

So, so, somehow did you lost interest? I lost interest? Yes, I wanted to ask you also about that story about President George W. Bush. I didn't realize you and Barbara Bush were friendly. Obviously George W. Bush's daughter twins with Jenna Bush Hager, and you went to Kenny Bunpoort with kind of your whole crew. Right. Yes, we went there and I didn't want to go there.

I was resistant, and they were like, no, no, come on, well, you don't take this opportunity away from us, Chelsea. We want to go to Kenny Buckport. We want to go to the Bush Compound. And it was to play pickleball. Another ridiculous aspect of that day.

I know we'll discuss pickleball in a moment. Because I'm a pickleball lover, you're a pickleball hater.

I would expect nothing less than you being a pickleball lover.

I know that you would love that. That is so funny. And then I know you love skiing top lists. I mean, we're two very different people, Chelsea, two peas and some sort of odd pod exactly exactly. And George W. Bush charmed the pants off you. Well, not literally, but he was charming. He was definitely charming, you said. The way the former president paid attention to and spoke with my brothers made all my guard rails fall away. He charmed me. I found him delightful with his riggage, good looks, and he had dimples too, which helped me rationalize these new feelings as so I reminded myself that it was really Dick Cheney who was the puppet master responsible for the war in Afghanistan and the response to nine to eleven. This is why I could never be a politician or jurer. I would constantly change my mind based on people's dimples and good looks. He is very charming, isn't he.

Yes, and he's very nice, and so was the former First Lady Laura Bush. And she's got dimples too, So it was kind of like a dimple affront.

You know what I mean.

I couldn't. I had no defense against all those dimples. All right, why do you hate tickleball? Chelsea Handler? And I'd like to remind you I was literally on the cover of Pickleball magazine. Just if anybody is interested coffees, you're still available. I just was.

Thinking, though, this is off topic, but I was just thinking when you were telling me about the Jennifer Anison thing and how your feelings were hurt, I was thinking, I'm like, I feel like I've publicly defended you a lot. And then I was like, oh, no, I haven't had to, because you don't need defending.

But I do. I want you to know how.

Many times I've brought up that Sarah Palin interview to journalists where I'm like, Katie Kirk did not receive the credit she deserved for taking down Sarah Palin, because if it were not for Katie Kirk's interview with Sarah Palin, she would have become the vice president. Like that was at a time where discrediting someone actually mattered, and you did that.

So I wanted to say I wanted to put that on the record.

Thank you, Chelsea. I do think actually I got a lot of credit from people and journalists because you're right, it's so interesting. I mean, there's a whole another conversation we can have another time or off the podcast. But you know, it doesn't really matter now these kind of interviews because everyone is so cemented in their views that they would a not see it or be call it biased or whatever. It just it's we live in a world where up is down and down is up and there's no kind of nuance. It's just black and white and it's crazy. But thank you. I'm very proud of that interview only because I think it was fair and I think it was very revelatory that she was not ready for prime time and really not equipped to run the country. And at the time, people may have forgotten that John McCain had had cancer four times, and you know, he was considerably older, and you know, there was a real possibility that he could have you know, I really like John McCain. Yeah, me too, and uh but you know, that was a very powerful position to be a heartbeat away from the president at that moment in time, and Obama at that moment was also flatlining in the polls. You know, he kind of dipped and I always thought he should have sent me a bouquet of flowers. But that's okay, Yeah, yeah, yeah, right, anyway, thank you. I appreciate you pointing that out. But back to pickleball, Why do you hate it so much?

That's too important, that's get it back to the basics.

I don't hate pickleball.

I just think it's ridiculous how enthusiastic people are about it, and how.

You're kind of a contrarian. You love to hate things that people love. Yes, it's a cult.

When there's a cult like reaction to something I have, I removed, I'm like, oh, even if some everyone's watching like, you know.

Really like the Menenda's brothers.

I have to wait until everyone's done and then I go in because I don't like to I don't like to be led.

I have to feel like it's my own decision. You know. Yeah, I have a little of that in me too. You know, if something is super popular, I kind of tend to not like so I kind of I totally get it. Yeah. So, but pickleball just is.

I had my girlfriend, my girlfriend Wendy call me one day and she said, oh my god, I played pickleball yesterday.

She goes, I'm so sure today, and I.

Just fell over laughing, and she was so offended. She was like, am I come on, you're sore from pickleball. That's not even a real sport. And then she got so she kept she kept doubling down. You do move around a lot, Chelsea. No, I know, I know you do move but she she was doubling down on it and getting so defensive that it just made me realize how seriously people take this pickle It's just too much.

It's like everyone needs to relax. Meanwhile, I also loved you talking about your nieces and nephews, and I know people have offered their unsolicited opinion about the fact that you have chosen not to have kids. You never really wanted to have kids. But one thing that comes through in the book is how incredibly maternal you are and how generous you've been to so many people, your nieces and your nephews and obviously your siblings and your friends. And when people understand these deep, profound relationships you have with so many children, do they shut up and stop judging you for not having your own? Yeah?

But I mean the people that are really judging me about not having children aren't around me, you know what I mean. Yeah, they're not seeing this, so i'd ever even you know, when I was thinking of things to share in this book that I hadn't shared before, that was an element that I realized, Oh, I have so many of these close relationships, and people, don't people just assume I hate children.

It's like, no, I don't hate children. I just don't want them.

It's a big difference, because you know, it's to me, it's like you know your taste in things.

It's like do you like purple or do you like blue?

I don't know that.

It's just a choice that is innately mine to make and the idea that anyone would have any misgivings about it or opinions about it is ludicrous and so stupid. And it's also why I wanted to share it to the book is an example of the bandwidth that you create for yourself when you don't have your own children, and how many other children's lives you can impact just by the freedom of not having your own family.

Yeah. I think, especially with public figures, it's so easy to make them completely one dimensional, right, and to stereotype them and put them in a box and kind of say they are this. But I always think of Walt Whitman and the fact that he said we contain multitudes, and it's very hard, I think, when you're a public figure to make that clear to people. And I think you know, that was a really great thing for you to include. And I love the letter you wrote to them about being polite and respecting. I mean, it was a long letter where you kind of had had enough of them in your house during COVID, right Chelsea, it was during COVID, and you basically said, these are my expectations for you. I thought that was such a great letter. I think a lot of people would like to xeroxet and hand it out to some of their relatives. I don't have that situation, but you know, I think it's easy to take advantage of people and not treat people respectfully. And I love you know that you said you need to be respectful of people who come in my house and do things. I think which was a message of be as kind to the doorman as you are to the CEO. Basically that everyone deserves or respect. What was their reaction to that letter. Were they taken aback or did they appreciate it in hindsight? I think, you know, after a while they did it.

At first, I think everybody was very defensive, you know well who it was very much like that. And then when they sat back and thought, like, why would I take the time to write this letter?

It was actually after several vacations.

It was not just COVID, it was we had been on several vacations together during COVID right over the years too.

You know, I want to spoil my family.

I always have, and I was part of the problem, admitted, I was setting up these really lavish vacations and thinking everyone was just going to behave gratefully forever.

So yeah, it was a wake up call for all of us. Yeah, that's true. You're right, I think for yourself too. We're almost out of time because I know you're doing like eight thousand podcasts to promote this book. But I want to ask you about your love life if I could. I know that you decided you didn't want to write a book about falling in love with Joe Cooy because you had broken up. Then you didn't want to write a breakup book. You write a little bit about that, but you don't write too much. And I'm curious if because this was your first public relationship, right and people knew about it, did you decide I don't like that, I'm not going to share that side of my life with people. I've got to keep something sacred in private. Well, it's just more.

For the people that I'm involved with that are private people, you know what I mean, Like, if they're not a public person, it's kind of it's silly to drag them into the public life, Like why would anyone want that? So I'm old enough now to know not to Like, if I'm with another public figure, then that's a different story, right, Right, But if I'm with a private person, like I don't want anyone to have to be exposed to this.

And so I know you want a lot of lovers, and I commend you for that, Chelsea, and just please, you know, make sure you have protection. But I mean, do you yearn for you know, I'm a real relationship person. You know, I'm like a one man woman. And do you ever yearn for that? And are you in a relationship now? Can you spill the tea with me a little bit.

I'm in some casual things right now. I wouldn't call anything a relationship. I'm having a lot of fun and with people that I like and that I know.

But do I yearn for that? It is not something that I yearn for.

It's not something that I would completely renounce and say it's never gonna happen.

But no, it's not something that I need.

I Again, it always comes back to like read them like I want to sleep in.

My own bed. I want to be alone a lot of the time.

I love having visitors, but I'm never gonna I'm not living with some man, you know what I mean, or any.

Man ever ever. But maybe I mean, you're it sounds like you're not maybe a part time situation, a part time situation, but you're open to a deep relationship. Yes, of course. Of course happened to Joe Coy. Can you tell me or not? Really?

I mean we just had different ideas of what a relationship was like, and I wasn't up for that kind of relationship.

Uh huh. He wanted to be sort of more together all the time, and you wanted to see him a lot of time. Yeah.

Yeah, a lot of togetherness and a lot of just kind of old fashioned ideas about relationships.

I was like, I mean, that's just not who I am.

And you know, everyone knows who Anyone who knows me knows how I feel.

Yeah, it shouldn't be a surprise. Yeah, definitely. Well, I know this is coming out in your birthday. You're turning the big five. Oh gosh, I'm jealous, Chelsea. Do you know that in January I turned sixty eight? Oh but so what that's amazing.

Sixty eight is amazing.

Look at you. You still are cute at sixty eight.

You're still so cute.

I always say this about you, and I've said this to you, that you have one of those spaces like Jennifer Aniston. Ironically, that will always be pretty like as a woman, no matter what age, You'll always have this cute pirkiness, like this youthfulness that and you still do you still do have that.

Thank you. I wasn't fishing for a compliment, but I'll take it anyway. And by the way, I like Jennifer Aniston. I don't want her to think there's bad blood between us. I'm sure she's really concerned, but I really think she's great. All right, where are you jetting off to next Chelsea? Well, I'm here in Whistler. I'm at my house in Whistler.

I have some friends that are in for the weekend and we're going to have a little preliminary birthday party for me this evening with a bunch of my scheme, my ski family, and my ski friends here. So that's what I'm getting ready for today and then I'm off to New York.

I always love seeing videos of you skiing topless.

Well, there'll be a new one coming out on my birthday. They're editing it right now. Yeah, what's your relationship? I'm sorry, I meant to ask you this because I'm curious. What's your relationship with drugs?

And alcohol these days, Chelsea, because I know you've kind of you know, it will also shock you that I'm not really into drugs and I drink very rarely occasionally, you know, I drink wine or I have a cocktail. But You've had this very interesting kind of on off relationship with drugs and alcohol, and I know, during this kind of intense period when you started meditating and taking care of yourself and really kind of to figure out what was going on inside of you, you gave it up, and I'm curious what the situation is now.

Well, funnily enough, I had this. I had to get shoulder, I had to clean out. I had an infection of my should So that forced me into a month of sobriety because I'm on intravenous antibiotics every day, so I haven't had it well. I just had to drink yesterday for the first time, or the day before.

Anyway, it was a month that was nice. I welcomed it.

It was a nice kind of breather before I had to hit the road and do all my press for my new book.

So that was nice.

I mean, my relationship is I'm always pro I'm always pro microdosing alcohol I have mushrooms. Do you like mushroom love LSD microdose? I love edibles, I love marijuana. I love all of it. I mean that's never really changed, so it just depends. I go in cycles. Sometimes I love everything. Sometimes I don't do anything. But I have a pretty healthy relationship with it. I've never gotten to the point anytime I've been in my youth and gotten to the point where I thought I was abusing it. I've taken a long break, so I never wanted to get to the point where I had to give it up. And I think I've done a pretty good job that. I was going to say. The book is called I'll Have what She's having. That sounds very appropriate given what you just said. I've never had mushrooms, I know, but mushrooms are so fun. You would just laugh your ass off, Katie and that. And I know when people can do druves or not, you would love mushrooms, you would.

I light micro dos, just the giggly kind, all right, Well, duly noted. Maybe if I do it one day, I'll do it with you. Yeah, I know you like to giggle, so you're gonna like it. All right. Well, I'm so happy to see you. Congratulations on the new book. It was really fun being with you and talking to you, and good luck on the book tour. Thank you so much, Katie. Where are you going to be all over the country?

Yeah, I'm coming to Northvale, New Jersey on the twenty fourth and the ninety second street, Why the twenty fifth?

Then Boston. Oh, who's interviewing you at the y Tinks? Oh? Fun, Tinks is interviewing me?

Yes, and then I'm going to Boston, Cincinnati, Seattle, La. So go to Chelsea Hamler dot com if you want to come see me on my book tour where I'll be giving talks and be in stores.

Yeah, okay, great, all right, We'll have fun and big kiss and thanks Chelsea.

Love you, Katie.

Thanks for listening everyone. If you have a question for me, a subject you want us to cover, or you want to share your thoughts about how you navigate this crazy world, reach out send me a DM on Instagram. I would love to hear from you. Next Question is a production of iHeartMedia and Katie Kuric Media. The executive producers are Me, Katie Kuric, and Courtney Ltz. Our supervising producer is Ryan Martz, and our producers are Adriana Fazzio and Meredith Barnes. Julian Weller composed our theme music. For more information about today's episode, or to sign up for my newsletter, wake Up Call, go to the description in the podcast app. Visit us at Katiecuric dot com. You can also find me on Instagram and all my social media channels. For more podcasts from iHeartRadio, visit the iHeartRadio app, Apple Podcasts, or wherever you listen to your favorite shows,

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