Inside Chelsea Handler’s wild dating history — from 50 Cent to Bobby Flay

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Who is successful Chelsea’s (love life) lately?

The comedian has spoken candidly complete nan years astir her short-lived romances — and insisted to Kristin Cavallari successful a May 2026 podcast section that she is “not a commitment-phobe.”

At nan time, nan Daytime Emmy victor told “Let’s Be Honest” listeners, “I don’t enactment excessively precocious to nan party. I cognize erstwhile to wrap things up. … My life is truthful f–king saccharine and nice. I conscionable don’t want immoderate disruption to that.”

Chelsea Handler (pictured supra successful May 2024) hasn’t been awkward astir sharing her making love history complete nan years. GC Images
While nan comedian (pictured supra successful February 2025) likes to get “out” earlier relationships are “locked in,” she has denied being a “comitment-phobe.” GC Images

The erstwhile “Chelsea Lately” big noted that she doesn’t “have a problem being religious for 5 aliases six months aliases 2 years if [she is] really successful love” — but erstwhile things get “locked in,” she’s “out.”

Handler clarified that she isn’t “scared,” adding that she doesn’t walk her azygous days “pining and hoping that [she’ll] meet someone.”

Page Six is revisiting her relationships and flings below, from rapper 50 Cent to personage cook Bobby Flay.

Ted Harbert

Handler’s longest narration was pinch Ted Harbert (pictured supra successful December 2009). Eric Charbonneau
The duo (pictured supra successful May 2008) dated for 4 years earlier calling it quits. Patrick McMullan via Getty Images

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During nan May 2026 sitdown, Handler noted that her longest romance lasted 4 years, referencing her clip pinch Comcast CEO Ted Harbert.

More than a decade aft nan duo’s 2010 breakup, Handler divulged nan threesome experience pinch a female masseuse that led to their split.

“I was very turned connected by this female [and] … ended up hooking up pinch her respective times without nan guy,” she said connected “Radio Andy” successful 2023. “That’s erstwhile I knew it was clip to break up pinch nan guy.”

Handler antecedently blamed activity connected their narration demise, telling Marie Claire successful 2012, “I would travel location from work, and Ted would beryllium like, ‘Do you want to watch your show?’ and I’d beryllium like, ‘No, I conscionable came from my show. That’s nan past point I’d want to do.’ That was nan logic it didn’t activity out, ultimately.”

Dave Salmoni

Handler was linked to Animal Planet prima Dave Salmoni successful 2010. FilmMagic
She joked astir their breakup successful a 2010 “Chelsea Lately” monologue. E!

Handler and Animal Planet prima Dave Salmoni dated successful 2010 — and she revealed their breakup successful a “Chelsea Lately” monologue.

“Up until a mates weeks ago, I was moving very intimately pinch Animal Planet, but unfortunately, that statement was terminated,” she joked.

“However, I enjoyed being successful furniture pinch them and whitethorn hook up for an occasional project,” Handler added.

50 Cent

Handler and 50 Cent (pictured supra successful April 2026) were an point successful 2011. WireImage
The Daytime Emmy victor has since dubbed nan “sweetheart” rapper (pictured supra successful April 2026) her “favorite ex.” Getty Images for Global Champions Arabians Tour Miami Beach

Handler has dubbed 50 Cent, whom she dated successful 2011, her “favorite ex” — past took it back erstwhile he endorsed Donald Trump for president successful 2020.

However, she gushed astir nan “sweetheart” successful a January 2023 Entertainment Tonight interview, calling him “fun to beryllium around.”

She recalled, “My friends loved hanging retired pinch him. I loved hanging retired pinch him. It was a beautiful short-lived romance, it was only 2 months. But yeah, if I saw him I’d decidedly person a portion pinch him.”

The erstwhile mates sewage together aft nan Grammy victor sent Handler “dozens and dozens of roses,” she told “House Guest” podcast listeners successful December 2025.

Andre Balazs

Handler was pinch Andre Balazs (pictured supra successful May 2013) betwixt 2011 and 2013. Donato Sardella
She has referred to her romance pinch nan businessman (pictured supra successful April 2013) arsenic “toxic” and “draining.” WireImage

Handler and businessman Andre Balazs dated betwixt 2011 and 2013.

The romance “knocked nan upwind retired of” nan character and “drained” her, she confessed connected Marc Maron’s “WTF” podcast successful 2012.

She explained, “It was highly clip consuming and it was really, really difficult for maine to attraction connected thing astatine all. He lived successful New York and I lived successful L.A., and it was a constant backmost and forth, flying and gathering each other. … It was conscionable exhausting.”

Handler later characterized nan romance arsenic “toxic” connected “Call Her Daddy” successful February 2025, claiming it made her a “paranoid … worst version” of herself.

Without naming Balazs, she elaborate her ferocious move pre-breakup, revealing, “I had 17 [trees] put connected either broadside of his driveway. … Every autumn and each spring, I get a matter from him saying, ‘I can’t judge I mislaid you. Do you want to travel and spot your trees?’ And I say, ‘I’m not interested.'”

Jo Koy

Handler and Jo Koy (pictured supra successful April 2022) were friends earlier dating. Penske Media via Getty Images
The brace were together betwixt 2021 and 2022. Instagram

Page Six collapsed nan news successful 2021 that Handler and chap comedian Jo Koy were together aft 2 decades of friendship — but nan brace called it quits successful July of nan pursuing year.

The erstwhile “Chelsea” big had “no choice” but to extremity things since it “would person compromised [her] ain worth system,” she said connected nan “Armchair Expert” podcast successful 2025.

Handler explained, “We had a mates of instances wherever it was evident that we had different ideas astir togetherness and nan magnitude of clip we would walk together and nan expectations of maine arsenic his girlfriend, which to maine were very outdated, old-fashioned and not going to work.”

She, who didn’t “for 1 2nd uncertainty [her] decision,” clarified that she and Koy ended their relationship successful a “vulnerable, mature [and] patient way.”

Bobby Flay

Handler savagely called retired Bobby Flay for being a “cheap” day successful May 2026. ABC via Getty Images
She branded her azygous day pinch nan personage cook (pictured supra successful May 2026) a “messy” one. Chris Rodriguez /AdMedia / SplashNews.com

Handler called retired Flay for “being” inexpensive while describing their azygous “bad” day to Cavallari successful May 2026.

Not only did Handler put nan “penurious” restaurateur connected blast for erstwhile sending room work to her edifice room and leaving her pinch nan measure aft immoderate “talking” and “flirting,” but she eviscerated their day arsenic well.

“It was conscionable like, messy,” she declared, insisting Flay was not her “match.”

Joe Largura

Handler and Joe Largura went nationalist pinch their romance successful March 2026. chelseahandler/Instagram
The duo met successful November 2025 successful Las Vegas. chelseahandler/Instagram

Handler hard-launched a caller romance, pinch her beau subsequently identified arsenic building executive Joe Largura, successful March 2026.

The mates met successful November 2025 astatine a Las Vegas blackjack table, quickly taking their romance to nan adjacent level pinch a travel to Antarctica.

“I’m still going beardown pinch this guy,” she told Las Vegas-Review Journal. “It’s hot, and a female for illustration maine needs a large move for illustration that.”

Mystery men

Handler (pictured supra successful January 2026) stayed quiet astir nan enigma man she dated nan erstwhile year. Getty Images for Critics Choice Association
The erstwhile “Chelsea” big (pictured supra successful January 2026) has besides refused to name-drop nan “serious” character she erstwhile went connected a “boring” day pinch — aliases nan A-lister she had a “nice small affair” with. Getty Images for Critics Choice Association

On “Let’s Be Honest” successful 2026, Handler refused to place a “serious” but “solipsistic” character who spent their full day talking astir himself — and teased a “nice small affair” pinch different enigma A-lister.

She besides played mum connected “Call Her Daddy” successful 2025 erstwhile describing a caller man successful her life “out of respect for his privacy.”

Handler said, “We didn’t really go lovers until astir six aliases 7 months ago. I invited him to Mallorca connected a travel pinch a group of friends. … I’ve known him for years. I’ve ever been attracted to him, but he was not available. I ever person wanted personification for illustration him successful my life.”

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