Chelsea Handler Talks Turning 50, Dating, Leaving ‘Bad Behavior’ Behind

Chelsea Handler has been working her entire life. Her first gig, at age 10, was running a lemonade stand — she spiked her product, and the business did gangbusters. Then she moved on to childcare, babysitting a boy four years older than she was. As an adult, her tenacity and quest for financial independence brought an onslaught of jobs, including shows from the 2002–04 hidden-camera blast Girls Behaving Badly to the 2007–14 talker Chelsea Lately; six New York Times bestsellers; a podcast; and multiple standup specials. She never stops hustling. And for the past decade, she’s been just as diligent in her private life, working hard on herself.

Handler’s comedy has given her a reputation: brash, direct, sometimes maybe even obnoxious. But her seventh collection of essays, I’ll Have What She’s Having — which arrives on her 50th birthday, February 25 — reveals that the newest, truest version of Handler is kind, generous and seeking.

“You want to get rid of the bad behavior that’s hurtful to others or hurtful to yourself, and also adopt this new version of you,” she exclusively tells Us Weekly of her evolution. “I don’t want to lose all the edge I was naturally born with — that’s who I am — so it’s a bit of Whack-a-Mole. You’re like, OK, I’m auditioning different versions of myself, seeing which ones make the most sense for this improved version of me.”

She talks to Us about becoming the best Chelsea she can be — and having all the fun doing it.

You recently said you’re tired of people asking how it feels to be turning 50. It’s like they expect you to be depressed, because they think being a woman of a certain age — especially one who’s single and child-free — is the ultimate disaster.

The narrative has to change. When I was in my 20s, I was trying so hard, with every eating disorder you could imagine, to have this body that I have when I’m about to turn 50. I look better. I’m smarter than I ever thought I’d be. I’m interested in all the right things. In my own judgment, I’m not shallow. I don’t sit around and watch stupid reality shows. I educate myself. When I have a chance to read a book, I pick it up. I’m proud, and I’m only getting better. This idea that women lose their value at this age — look at Pamela Anderson and the year she had. Demi Moore. Nicole Kidman. Hollywood is a representation of what’s to come. Women are unstoppable, and there’s nothing anyone can do to shut us up.

That’s an amazing perspective.

The good thing about aging is that you start to care less about the past and the future and you are able to be more present. Being present is the best supplier of good times. I was reading an article the other day that said if you can get through the next 10 to 12 years, there will be scientific innovation that will allow you to stay alive and remain healthy until you’re, like, 120 years old. And I thought, Who the f— wants to live until they’re 120? First of all, I can’t afford to live that long. Second, am I going to be doing standup at 120? I have no desire to see what this world is coming to. I’ve seen enough, it’s a wrap. I’m not scared to die; I am pretty scared not to live.

What’s the best way to do that?

One thing you can do is just provide more love, more joy, more comfort to all those people you love and care about — to really, really double down on your kindness and compassion. You can make a difference in someone’s life, and if we choose to do that, then you are bringing the vibe higher. Even if it’s only one or two people you come into contact with in a week, it doesn’t matter: There’s a domino effect that’s powerful. People think that’s just woo-woo talk, [but] it’s pretty concrete.

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In the book, you call yourself an interloper. You take control of situations and actively try to make them better. There’s a great example of you writing a letter to your nieces and nephew about their “shortfall of manners” while traveling with the family.

Nine times out of 10, it ends in a positive way, and people are grateful. And then there are situations where it does not work out, where the person cannot hear you [or does] not want to hear you. I’m not out to hurt anybody — I want everyone to succeed. So if you’re going to tell someone with love that there’s a situation, I think that’s sisterhood. And I always want to be a sister.

Your 2019 book, Life Will Be the Death of Me, delved into your brother Chet’s death when you were 9 and your 
experience with therapy. This title picks up after that process, when you’re applying everything you learned, which sounds very hard.

It’s kind of a trial-and-error thing. 
I am so many things to so many people, but who am I to myself and what are the most important traits I have that 
I don’t want to let go of? And which are the ones I want to be better at?

What did you come up with?

I wanted to be more patient. If I talk to a moron, it’s clear by the look on my face 30 seconds into the conversation what I’m thinking. I don’t have a poker face. I don’t have time for people I don’t think are intelligent, and that’s a pretty narrow way of looking at the world. You have to figure out a way to have more room for patience, more room to change your opinion… and to be really careful of other people who might be more fragile or sensitive. That’s been a big lesson for me because I’m not those things. I just assume other people will know where I’m coming from, and that’s a misstep. Even though I’m going to be 50, I still want to grow up. I’m always going to be an asshole, but I want to be a grown-up asshole.

What do you think people’s biggest misconception is about you?

God, I wouldn’t even know. I don’t know what people think about me anymore. That’s how disinterested I am.

Twenty years ago, would you have thought you’d get to that place?

When I was in my 20s, I don’t think I really cared either, but it was a different kind of not caring. It was more arrogant. Now I’m softer, but I also realize how silly it is to worry too much. I mean, of course I care what people think about me, but I don’t let that run me. I’m too solid of a person to be worried about stuff like that. I have bigger fish to fry.

Jo Koy, whom you dated from 2020 to 2021, is a big presence in the book. Your relationship was so out in the open, and you write about how important that was to him: “Jo lit up anytime I spoke about him publicly, so I did it any chance I got.” Was there a part of you that wrote about him for him?

When I got this book deal, the editor and I were in conversation about me falling in love in such a public way and how well that was received by everybody. We had so many cheerleaders. I guess people were surprised to see me in that state. I wouldn’t say I did it for him; I would say he loved that aspect of it, so I served that up. We did have a long, funny history. I had known him years ago on Chelsea Lately. I used to bury him on the roundtable. The fact that I was now having sex with this person needed some explaining because I was just as surprised as anyone. And I had fallen in love with him — I was like, Oh, my God, how did this happen?

What’s your current dating life like?

Dating is wonderful. I understand now what kind of dater I am, and this is what I am: I want lovers all around the world. I’m not a liar. I will be very honest and upfront with anyone I’m dating that you may not be the only one, and if you need to know, I’ll let you know, but hopefully you don’t need to ask any further questions.

So no marriage goals?

I’m not the marrying kind. I am not looking for children. I just want to have lots of love stories. I feel like that’s the most romantic way to look at love. And I’m glad I know that about myself because I think so many women are starting to be more open about [the fact that] this Prince Charming nonsense we’re sold is so silly.

I’m just recovering from shoulder surgery. I’m seeing someone, and he’s like, “Let me know when you want me to fly down.” I’m vulnerable, I’m in pain, I have to get antibiotics intravenously every 24 hours. I’m like, “No, no, I need to be alone during this time.” I’m an independent woman. I don’t thrive with dependency. I’d rather wallow in my own misery alone and watch 40 hours of television on Vicodin than have someone I’m not paying take care of me. Do you understand?

Absolutely.

Women are really actualizing this now: “Wait a second, I have value that doesn’t involve a child [or] a man. And I don’t need any of that to succeed, to be happy, to have freedom,” which is something we don’t talk about enough until [that freedom is] threatened.

But that’s the way I’ve felt ever since I was a little girl. I just wanted to 
grow up and be free to express myself. 
I haven’t had a boss in 10 or 15 years, 
and I’m managing to do just great.
I have three houses [in L.A.; Whistler, British Columbia; and Mallorca, Spain]. I have a wonderful dog [her chow chow, Doug]. My life is filled with dogs, with friends and with family. I want everyone to know their value. Find out your purpose and go after it. This is the only chance you have.

It seems like women also sometime dim their own light so other 
people don’t feel diminished.

I hate when people are self-conscious. I hate that for them. I wish I had an Ozempic needle filled with self-confidence that I could just go around stabbing everybody with, because if every­one were self-secure, it would be so much easier. I have a lot of needles, but I don’t have that.

Speaking of needles… or at least drugs: You talk a lot about psychedelics and the positive impact they’ve had on your life.

They’re just a great provider of joy. They’re mind- and heart-openers. And I think especially when you’re in a loving group of friends and you microdose, whether it’s mushrooms or LSD, you can have really meaningful, even more powerful experiences. If the setting is right, there’s only one way those experiences go, and that’s up. [In Mallorca], the setting is beautiful. There’s not a bad vibe that could happen because you’re in such a magical place and we’re on vacation. It’s almost risk-free. When I ski a lot, I’ll microdose because it just makes you appreciate nature even more. It makes everything glisten.

And again, it’s microdosing, so it’s not like you’re off your rocker [or] you’re just sitting down staring at a leaf for 20 hours. You’re actually going through the day [with] a little pep in your step. Everything’s a bit more magical.

You’re clearly a very secure person, but do you have any insecurities?

I have this little bunionette growing out on the side of my foot. I’m insecure about that.

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Is that an actual term? Bunionette?

I’m calling it a bunionette because that sounds more petite. I’m wearing toe spacers right now. I’m also insecure about my dancing. I can’t dance.

Right, you say that in the book.

I can’t dance. I promise you it’s true. 
I can’t.

Do you enjoy it?

No, I don’t like it. I have no rhythm. It’s embarrassing. I did Jennifer Hudson’s show the other day, with the spirit tunnel. I was walking so fast through that thing before I had to do a dance move. But as I turn 50, I’m like, This is the one thing I’m insecure about, and I’m going to start dancing whether I look like an asshole or not. Who gives a s—? I can’t be good at everything.

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