Chelsea Handler isn’t known for holding back on her innermost thoughts, and she certainly lived up to her reputation for unfiltered conversation in a can’t-miss interview with Katie for the latest episode of her podcast, Next Question.
Handler’s new book, I’ll Have What She’s Having, is a characteristically hilarious and vulnerable collection of essays that tell the tale of how this one-of-a-kind comedian became the woman she always wanted to be. During her chat with Katie, Handler explains the idea she originally had for the book (and why she decided to pivot), along with how she developed her “hustler” mentality, how she’s feeling about politics under President Trump’s second term, and a whole lot more.
Ready to dive in? Read on for a few highlights below, and watch the entire interview in the video above.
How Handler’s breakup with Jo Koy transformed her plan for her book
“This book came around when I was dating Jo Koy, and I was very publicly in love and we were demonstrative about it, and everyone was eating it up,” Handler explains. “People were happy for us and cheering us on. And I had never been in 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. My editor had asked if I wanted to write a book about falling in love, and I said, ‘Sure, I would love that.'”
But the universe had other plans.
“Then we broke up,” Handler says. “I was like, ‘Well, I guess I can’t write that book now.’ And then [my editor] was like, ‘Well, what about the breakup?’ Because I was handling the breakup in a much different way than I had in previous relationships.”
After thinking about it and deciding a breakup book didn’t feel organic to her, Handler chose to go in a fresh direction.
“I just thought, What do I have to say? As a woman, as I’m turning 50, as I have grown up in this world, especially in the last 10 years, I’ve become so different — a person who’s constantly searching to find more meaning and more purpose,” she says. “So when I really sat and thought about where my life began and what I’ve done with it, I thought, Oh, what about a nice guide for women to check in with themselves and be questioning: Am I on the right track that I want for myself, or am I on a track someone else put me on?“
How she developed her go-getter spirit — and why she says it’s so important
“It’s a combination of your surroundings and your nature that you’re born with, but I’m definitely a hustler. And I think that’s great. I mean, you’re a hustler, too,” Handler told Katie. “I wanted a big, loud, brave life. I was 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.’ I have no idea where my confidence came from, but I believed in myself and I thought, OK, this is how it’s going to be.”
Seeing that development in her own life is yet another reason Handler wanted I’ll Have What She’s Having to prompt readers to assess their own progress — and where they want to go from here.
“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 check in [with themselves]. B Because 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 sometimes get away from ourselves and the essence of who we are.”
One thing that’s been especially helpful to Handler along the way? Therapy.
“We all could use a little bit more compassion and more empathy,” she says. “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 able to deal with more difficult situations in a calmer, more loving way. Not every conflict has to be an explosion.”
Handler’s take on our “alarming and revolting” political moment
President Trump’s second term began with a bang and hasn’t slowed down since, and Handler says she’s thinking carefully about how to conduct herself this time around.
“I’m 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,” she says. “You know, I’m in that group where [Trump’s policies] are obviously not as much of an immediate threat to my life. I don’t know what to say about everything that we’re reading and experiencing. My one thing when we came into this administration was like, I’m not letting them steal my joy again … All you can ever really choose is how you respond to a situation, and I’m going to choose to be calm and double down on all the good stuff, and do what I can do with people that I come into contact with in my communities — and obviously be there for the bigger actions when they’re necessary.”
But Handler says she does see a bright side of the situation: That responding to Trump’s policies can be an opportunity for Americans to come together.
“In my 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,” she says. “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’re not going anywhere, and because we’ve discovered that our only value doesn’t come from being a mother or a wife. 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.”
