The Chelsea Handler Dating Playbook

If there’s one thing Chelsea Handler wants you to know about her dating life, it’s this: She’s not sorry. Not for the exes, not for the mushrooms, not for the dry spells, and certainly not for enjoying herself. During her appearance on We Met At Acme, Chelsea shared dating gems that would make Carrie Bradshaw blush—with the confidence of a woman who’s done the work.

“Open and Available for an Adventure”

Chelsea’s current relationship status? “I’m always open and available for an adventure, and I’m currently having one with someone,” she told host Lindsey Metselaar. And no, she’s not planning a wedding Pinterest board. “I’m not breakable. It’s okay if it happens, and it’s okay if it doesn’t. I’ve still got my shit.”

For Chelsea, dating isn’t about finding someone to “complete” her—it’s about sharing life with someone while staying whole. She’s been boy crazy before, sure, but these days? “Sometimes I date multiple men at the same time, not as often as I’d like, but I’m not here to be someone’s wife. That’s a side gig for me.”

The 50 Cent Tea: “He Was a Gentleman”

No Chelsea Handler dating conversation is complete without a mention of Curtis “50 Cent” Jackson. And yes, she spilled some tea that’s never made it to late-night TV.

“50 was one of the most considerate guys I’ve ever dated,” Chelsea admitted. “People always want the salacious story, but the truth? He was a total gentleman. And, by the way, hilarious. Like, truly funny—not ‘rapper trying to be funny.’ Just naturally quick.”

She laughed as she recounted a night they went out in New York. “He was like, ‘Let’s get out of here,’ and next thing I know, we’re in some insane suite overlooking Central Park, eating cheeseburgers at 2 a.m. It was ridiculous. But that’s what I like—fun, spontaneous, not taking anything too seriously.”

Chelsea did address the elephant in the room—politics. “People thought we’d fight about it, but he was surprisingly chill. He’d say, ‘Chelsea, I get it. We just see things differently.’ That’s rare.”

The Mushroom Mishap

It also wouldn’t be a Chelsea story without some psychedelic chaos. One story that didn’t make it into her book, I’ll Have What She’s Having? The time she accidentally dosed a first date.

“I was in London, having this amazing dinner with this gorgeous Welsh guy I’d been chatting with on Raya. After dinner, I asked, ‘Do you want to take some chocolate mushrooms?’ He was all in. We get back to my hotel, start kissing, and suddenly he pulls away and goes, ‘I think I’m gonna be sick.’ Next thing I know, he’s throwing up outside the hotel. Never saw him again.”

Chelsea’s takeaway? “My friends were like, ‘Why the hell are you dosing people on a first date?!’ And honestly? Fair point.”

Dating Like Chelsea Handler: The Takeaways

How can you apply Chelsea Handler’s unapologetic dating ethos to your love life? Here’s the cheat sheet:

• Own your adventure: Chelsea’s mantra is clear: “You can’t break me.” Date without attaching your happiness to the outcome. 
• Know your “icks”: Bad hygiene? Inflated ego? “I can’t do it,” Chelsea declared. “If you smell weird or you’re trying too hard—next.”
• Set the standard, then exceed it: Chelsea doesn’t wait for men to set the tone—she does it herself. “I’m fine being the funny one. It’s better that way.”
• Boundaries are sexy: Despite claiming she’s “terrible with boundaries,” Chelsea’s actions say otherwise. She’ll compromise out of kindness but never settle. “I’m not giving up my peace for anyone.”
• Enjoy the moment, forget the pedestal: “Just enjoy the night with them,” she advised. “Don’t fast-forward to ‘what does this mean?’ If it ends tomorrow, so what? It was still a great night.”
• Be clear about what you want: Chelsea credits her love life turnaround to clarity. “I once went three years without dating, convinced it just wasn’t for me. Then I told my therapist, ‘Actually, I do want love.’ Boom—met someone a few months later. You have to tell the universe what you want.”
• Humor is non-negotiable: “If you can’t laugh with me—or at me—we’re done. I need someone who gets the joke. Life’s too short for serious bros.”

Be Your Own Damn Soulmate

Chelsea Handler’s approach to dating isn’t about being cool or aloof—it’s about being complete. “You have to have your own shit going on,” she insisted. “Be someone you’d want to date. Have interests, read books, lift weights—whatever makes you feel powerful.”

And if you’re still searching for “The One”? Chelsea’s advice is refreshingly simple: “Stop cock-blocking yourself. Be clear about what you want, and it’ll find you.”

Or, at the very least, you’ll have one hell of a story to tell—mushrooms and all.