If you’ve ever watched Chelsea Handler for more than five minutes, you know she doesn’t do "mushy." She’s the queen of the sharp-tongued retort, the woman who made a career out of being child-free, fiercely independent, and unapologetically loud. But beneath that "I don't need anyone" exterior is a surprisingly rich, sometimes chaotic, and deeply human dating history.
Honestly, tracking who has Chelsea handler dated is like trying to map out a high-speed chase. It’s fast, there are occasional crashes, and the scenery changes constantly. From corporate titans and rappers to fellow comedians, her list of exes is as eclectic as her stand-up sets.
Most people think she’s just out there breaking hearts and moving on. The reality? She’s a serial "truth-teller" in her relationships, which—as any therapist will tell you—usually leads to some pretty spectacular breakups.
The Jo Koy Era: The One That Felt Different
Let’s start with the most recent heartbreak because it still feels raw for a lot of fans. For about a year, starting in 2021, Chelsea Handler and Jo Koy were the "it" couple of comedy. They had been friends for twenty years. Twenty! He was a regular on her late-night show, Chelsea Lately, back in the day.
When they finally went public, it felt like a romantic comedy trope come to life. The cynical best friend finally finds love with the guy who was there all along.
But by July 2022, it was over.
What went wrong? Chelsea’s been pretty vocal about it. In early 2025, she opened up on the Armchair Expert podcast, basically saying that while she loved him, she wasn't willing to "abandon herself" to make the relationship work. She mentioned "outdated, old-fashioned" expectations of what a girlfriend should be.
Translation: She wasn't going to be the quiet woman behind the man.
Even though they split, she credits Jo with "renewing her faith in men." It was a mature breakup—mostly. By early 2026, things seem a bit frostier, especially after she poked fun at his hosting gigs during award shows. That’s just Chelsea, though. If you date a comedian, you're eventually going to be the punchline.
The 50 Cent Experiment: Two Months of Chaos
If you want to talk about a pairing no one saw coming, it’s Chelsea and Curtis "50 Cent" Jackson. They dated for a hot minute back in 2011. It was short—only about two months—but the stories she tells about it are gold.
Why did they date? Apparently, he was persistent. He sent dozens of roses to her office. He took her to New Orleans. Her friends absolutely loved him because he’d show up at her house in a different luxury car every night—Lamborghinis, Ferraris, you name it.
"I realized he was borrowing all these cars from different dealerships," she joked recently. "I didn't know you could do that."
She even bought a "chocolate-colored" Bentley just to keep up with the joke, then got stuck with the car after they broke up. She calls him her "favorite ex" because he was sweet, didn't do drugs (which she jokingly said was a disappointment), and was the complete opposite of his "gangsta" persona.
The Corporate Power Play: Ted Harbert
Before the rappers and the comedians, there was Ted Harbert. He was the CEO of Comcast Entertainment Group—essentially her boss at E! during the height of Chelsea Lately. They dated from 2006 to 2010.
This was a heavy, four-year relationship. It was also a professional nightmare. Imagine coming home after a 12-hour day of filming your own show, and your boyfriend asks, "Hey, want to watch your show?"
Chelsea eventually admitted they couldn't separate business from pleasure. But there was a more "Chelsea-esque" reason for the split that she finally revealed in 2023: a threesome with a masseuse. She told Andy Cohen that she ended up being more into the woman than the guy she was dating. That’s a pretty definitive sign that the relationship is over.
The Hotelier and the Trees: André Balazs
Between 2011 and 2013, Chelsea was on-and-off with André Balazs, the man behind The Standard hotels. This relationship was... intense.
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They were a high-profile power couple, but Handler has hinted that it was a "toxic" situation at times. In fact, she recently shared a story on Call Her Daddy about an "unhinged" breakup gift she gave a certain ex (widely believed to be Balazs).
Supposedly, she had a bunch of trees planted on his property in a way that would eventually block his view or be a massive pain to deal with. It's the kind of petty move that requires a lot of planning and a healthy budget. You have to respect the commitment to the bit.
The "New Man" and the Current Vibe (2026)
So, where is she now? As of early 2026, Chelsea is back in the game. She recently teased a "steamy Antarctica rendezvous" with a new mystery man. She’s keeping the details close to the chest for now, but she told E! News that she likes meeting men "unexpectedly."
She also hasn't lost her edge. When rumors swirled about Tom Brady and Alix Earle in early 2026, Chelsea didn't hold back, calling the NFL legend a "total dud" and "boring." She clearly isn't looking for a trophy; she's looking for a sparring partner.
What We Can Learn From Chelsea's List
If you're looking for a pattern in who has Chelsea Handler dated, you won't find one. There is no "type." She’s dated the corporate suit, the rapper, the hotel mogul, and the funny guy.
But there is a theme: Self-preservation.
Chelsea’s dating history is a masterclass in knowing when to walk away. She doesn't do "sunk cost fallacy." If a relationship requires her to be less of herself, she’s out.
Actionable Takeaways for Your Own Love Life:
- Friendship is a solid foundation, but not a guarantee. The Jo Koy situation proves that even 20 years of history can't bridge a gap in core values.
- Don't date your boss. Seriously. Ted Harbert was a great guy, but mixing your paycheck with your pillows is a recipe for burnout.
- Keep your sense of humor. Even her "unhinged" breakups make for great stories later. If you can't laugh at the wreckage, you're doing it wrong.
- Vulnerability isn't a weakness. Chelsea admitted that being with Jo Koy made her realize she could be a partner, even if it didn't last forever.
Chelsea Handler is 50 now, and she's more vocal than ever about the fact that her life is full, whether there's a man in it or not. She’s lived in Bel Air, traveled the world, and built an empire. A boyfriend is just an accessory—preferably one that can keep up with her wit and doesn't mind a few jokes at his expense.
Stay tuned, because if history is any indication, her next "official" relationship will be just as surprising as the last.
Want to see how her perspective has shifted? Check out her latest tour dates or her podcast, Dear Chelsea, where she gives out relationship advice that is surprisingly—and sometimes brutally—practical.