Pop Culture

Chelsea Handler Thinks Women Need to Stop Treating Being Single Like a Crisis

May 27, 2026

Chelsea Handler is not a long-term person, but she’s okay with that, even though everybody else may not be. During her conversation with Kristin Cavallari on Let’s Be Honest, she talks about why relationships tend to lose their appeal after a few months, why getting older has actually made her feel more confident (and hotter), and the realization that she’s happiest when she’s protecting the life she’s built for herself instead of forcing herself into roles that no longer fit.

The comedian also opens up about the stretch of her forties when she “lost the plot a little bit,” admitting she had to learn how to slow down and stop trying to fix everyone around her, with therapy as her guide. She became more present, and with that presence came grounding. At this point in her life, she’s more interested in protecting her peace and the version of herself she worked hard to become.

Below are the highlights from the conversation, adapted from the episode.

Why don’t you want a long-term relationship?

“I am not a long-term person. I just am not interested in anything that comes after the six-month relationship mark. I’m not interested in dealing with your family or your issues. I am not interested. Like, I’m not at a place in my life—maybe that will change—but I’m not at a place in my life where I…want to be part of a unit. I want to have a good, sexy affair. I don’t want to be a couple. I just want to have somebody that I’m into and buzzing on, you know.”

What’s your ideal relationship setup?

“My ideal situation would be long distance. Someone who doesn’t live close by and someone who I see probably like every two weeks for like three or four days and someone who I can travel with, like go on fun trips with. That’s the most important thing: someone who has their sh*t together enough that they can afford to travel and that they have the desire to make that happen, you know what I mean?”

What changed for you in your 40s and 50s?

“So it’s just a great reminder as you age that you’re capable, that you’re competent, and that there’s different phases like seasons of life and like there’s times when you’re with someone, there’s times when your kids are young, there’s times where your kids are old, you know, like, and you just go with the flow instead of freaking out and being like this isn’t right, this isn’t right. I’m not in the right place…Once you ease into wherever it is you are, things become easier, and then you have like almost a magnetic attraction, not almost, it really is your energetic field, and your frequency that you’re operating on becomes attractive to other people…

…50 for me was more of a turning point, 40 was more of a crisis point. Like, I had a little bit of a midlife crisis because I had just left Chelsea Lately. I had started my Netflix show. Trump had been elected…It was uncomfortable and it wasn’t my finest hour I would say, but it got me to the other side of just like being a self-actualized person, like understanding what my shortcomings are, understanding what my strengths are, getting out of my head and getting into like my body and learning how to meditate, learning how to like breathe and learning how to like sit by myself and read books again. Like I had lost the plot a little bit, so I kind of doubled down, and now at 50 it’s just f**king awesome, I feel like if I had known that this was what 50 was gonna be like, I would have been so psyched.”

What was the biggest turning point during therapy?

“That not everybody needs my opinion on everything. Like, not to insert myself as a problem solver, kind of to recognize that sometimes people do want your help, and sometimes people are just venting and stop trying to fix everybody’s problems.”

Were you worried therapy would change your comedy?

“Yeah, I didn’t do comedy for the whole time I was going to therapy, and I went to therapy for a full 19 months, almost two years, and during that time I didn’t do stand up. I was like, I can’t be funny. This is too intense…I was hoping it would be like a two-month thing, but it wasn’t, and I wanted to just get it. I was like, give me the knowledge and information. I wanna be a better person, just give it to me. Download. Like I wish I had AI, you know…It took me a while to digest the information and then apply the information.”

What did therapy actually teach you about yourself?

“You are recalibrating your personality and like your personhood, like you’re becoming the best version of who you wanna be, so everything becomes sharper eventually. But it’s a little bit of a pathway, it’s not instant.”

What’s the biggest lesson you’ve learned from relationships?

“That I’m really at my happiest when I’m alone. I love it. I am like, there’s nothing to not be happy about.”

What happened with Bobby Flay?

“Yeah, I went on a date with Bobby Flay. That was pretty bad. He ordered me room service…Someone hooked us up. We were talking on the phone, flirting a little bit, and then I was at a hotel with some girlfriends. And I think we were filming for Netflix. I guess I must have been in like a different country…He knew the hotel well, and he wanted to order me room service, food for us. He’s like, ‘Let me order your food for you. I love that hotel.’ Maybe it was Vegas or something. Anyway…he ordered me [and my girlfriends] food. But then they brought me the bill, and I’m like, ‘What, what is this guy?’ And then like somebody was like, ‘Oh yeah, he’s really cheap, he’s really cheap,’ and I was like, ‘Oh, I hate cheap.’ Like I don’t, if you’re penurious, I’m not interested in you. I’m generous, and I like people to be generous with their money. And then we did end up going on a date, and it was just not a match. It was just like it was messy, messy.

What’s your rule for dating now?

“If a guy comes in, you have to be an addition, not a subtraction. And as long as you’re an addition, you can hang out.”

What’s your biggest issue with Hollywood?

“My issue with a lot of celebrities is the vapidity…Like being vapid, not giving a sh*t about anything but your f**king hair and your makeup and your clothes and being vapid, like I find that to be intolerable.”

To hear the full conversation, listen to Let’s Be Honest wherever you get your podcasts.