Chelsea Handler at 50: Still hustling and dreaming of margaritas

Chelsea Handler in Los Angeles on March 12, 2025. Handler has a new book out, as well as a stand-up special and a Las Vegas residency this year. — Photo: BETHANY MOLLENKOF/The New York Times

Chelsea Handler is unapologetic in her latest book, I’ll Have What She’s Having.

Well, of course, she is. She’s Chelsea Handler, and that’s always kind of been her thing.

There are many of the stories you would expect from the former host of the E! show Chelsea Lately in her seventh book, which came out in February, such as confronting rudeness in men, shamelessly propositioning Andrew Cuomo for sex when he was governor of New York and ruthlessly pushing out a business partner for a lemonade stand. (She was 10 at the time.)

But Handler also weaves in more life advice, a healthy dose of cheerleading (both for the reader and herself) and insights gained from therapy and various breakups.

The book includes chapters about her very public relationship with comedian Jo Koy, but fans looking for the details of the breakup will be disappointed: She doesn’t say much, and mostly speaks well of Koy. A sign of growth, she says.

“While I am sure that is of interest to people, I will no longer throw someone I once loved under a bus,” Handler writes.

“My sharing what exactly went wrong in our relationship would negate all the work I have done on myself while also creating a headline I don’t want to create.”

The main takeaways: She’s 50. She’s hustling. There’s a Netflix special and a residency in Las Vegas.

And she’s sure of herself. That’s all she needs, and she’s finally realised it.

In this interview, Handler discussed the new book and the newish Chelsea.

This conversation has been lightly edited and condensed for clarity.

You note that you essentially make a living being yourself. Does that mean you’re never off the clock?

I don’t think it means I’m never off the clock. It just means that I’m never not being really authentic.

And to be able to make a living by expressing myself and my true feelings feels like a big victory.

How are you different now compared to when you first rose to fame?

A lot less arrogant, a lot more grateful, a lot more self-aware.

And I don’t complain about working hard anymore. I used to crash and burn and want to quit my job.

Now I understand how important the breaks are and that the breaks are as important as the work.

You described your relationship with Jo Koy as true love. Without getting into details about why it ended, when it was at its best, how much did that make you rethink your stance on marriage, if at all?

I have considered marriage many times in my life, including within that relationship.

But the consideration of marriage and actually pulling the trigger are two different things.

I’ve been proposed to a couple of times, and then I ended those relationships shortly after the proposal because I realised, “Oh, we’re not on the same page.”

So it brings in the consideration when you’re deeply in love with somebody.

But it doesn’t change my ideology about life.

You once told The Guardian that you didn’t want to work your whole life. That you wanted to live on an island and drink margaritas all day by 40. How do you view work now?

I was very naive when I said that. I was thinking about that very quote – because I said it more than once – the other day, thinking: “Wow. I’m 50 and I’m working harder and hustling harder than I ever have.”

But yes, I still feel the same way. I would love to go live on an island and just drink margaritas forever, but it’s really not within my nature.

I am a hustler. I take a lot of pride in my New Jersey hustle. – By SOPAN DEB/© 2025 The New York Times Company

Chelsea Handler: The Feeling is available on Netflix.