Who’s been capturing Chelsea Handler’s heart lately?
Over the years, the comedian has openly discussed her brief romantic encounters, yet she assured Kristin Cavallari during a podcast episode in May 2026 that she is far from being a “commitment-phobe.”
During the episode of “Let’s Be Honest,” the Daytime Emmy winner shared, “I know when it’s time to call it a night. My life is incredibly sweet and peaceful, and I’m not interested in anything that might disrupt that harmony.”
The former “Chelsea Lately” host also mentioned that she has no trouble being faithful for periods as long as five or six months, or even two years, if she’s truly in love. However, she admitted that once a relationship feels too permanent, she tends to bow out.
Handler clarified that her approach isn’t out of fear, emphasizing that she doesn’t spend her single moments longing for someone to come along.
Page Six is revisiting her relationships and flings below, from rapper 50 Cent to celebrity chef Bobby Flay.
Ted Harbert
During the May 2026 sitdown, Handler noted that her longest romance lasted four years, referencing her time with Comcast CEO Ted Harbert.
More than a decade after the duo’s 2010 breakup, Handler divulged the threesome experience with a female masseuse that led to their split.
“I was very turned on by this woman [and] … ended up hooking up with her several times without the guy,” she said on “Radio Andy” in 2023. “That’s when I knew it was time to break up with the guy.”
Handler previously blamed work on their relationship demise, telling Marie Claire in 2012, “I would come home from work, and Ted would be like, ‘Do you want to watch your show?’ and I’d be like, ‘No, I just came from my show. That’s the last thing I’d want to do.’ That was the reason it didn’t work out, ultimately.”
Dave Salmoni
Handler and Animal Planet star Dave Salmoni dated in 2010 — and she revealed their breakup in a “Chelsea Lately” monologue.
“Up until a couple weeks ago, I was working very intimately with Animal Planet, but unfortunately, that contract was terminated,” she joked.
“However, I enjoyed being in bed with them and may hook up for an occasional project,” Handler added.
50 Cent
Handler has dubbed 50 Cent, whom she dated in 2011, her “favorite ex” — then took it back when he endorsed Donald Trump for president in 2020.
However, she gushed about the “sweetheart” in a January 2023 Entertainment Tonight interview, calling him “fun to be around.”
She recalled, “My friends loved hanging out with him. I loved hanging out with him. It was a pretty short-lived romance, it was only two months. But yeah, if I saw him I’d definitely have a drink with him.”
The former couple got together after the Grammy winner sent Handler “dozens and dozens of roses,” she told “House Guest” podcast listeners in December 2025.
Andre Balazs
Handler and businessman Andre Balazs dated between 2011 and 2013.
The romance “knocked the wind out of” the actress and “drained” her, she confessed on Marc Maron’s “WTF” podcast in 2012.
She explained, “It was extremely time consuming and it was really, really hard for me to focus on anything at all. He lived in New York and I lived in L.A., and it was a constant back and forth, flying and meeting each other. … It was just exhausting.”
Handler later characterized the romance as “toxic” on “Call Her Daddy” in February 2025, claiming it made her a “paranoid … worst version” of herself.
Without naming Balazs, she detailed her savage move pre-breakup, revealing, “I had 17 [trees] put on either side of his driveway. … Every fall and every spring, I get a text from him saying, ‘I can’t believe I lost you. Do you want to come and see your trees?’ And I say, ‘I’m not interested.’”
Jo Koy
Page Six broke the news in 2021 that Handler and fellow comedian Jo Koy were together after two decades of friendship — but the pair called it quits in July of the following year.
The former “Chelsea” host had “no choice” but to end things since it “would have compromised [her] own value system,” she said on the “Armchair Expert” podcast in 2025.
Handler explained, “We had a couple of instances where it was obvious that we had different ideas about togetherness and the amount of time we would spend together and the expectations of me as his girlfriend, which to me were very outdated, old-fashioned and not going to work.”
She, who didn’t “for one second doubt [her] decision,” clarified that she and Koy ended their connection in a “vulnerable, mature [and] healthy way.”
Bobby Flay
Handler called out Flay for “being” cheap while describing their single “bad” date to Cavallari in May 2026.
Not only did Handler put the “penurious” restaurateur on blast for once sending room service to her hotel room and leaving her with the bill after some “talking” and “flirting,” but she eviscerated their date as well.
“It was just like, messy,” she declared, insisting Flay was not her “match.”
Joe Largura
Handler hard-launched a new romance, with her beau subsequently identified as construction executive Joe Largura, in March 2026.
The couple met in November 2025 at a Las Vegas blackjack table, quickly taking their romance to the next level with a trip to Antarctica.
“I’m still going strong with this guy,” she told Las Vegas-Review Journal. “It’s hot, and a woman like me needs a big move like that.”
Mystery men
On “Let’s Be Honest” in 2026, Handler refused to identify a “serious” but “solipsistic” actor who spent their entire date talking about himself — and teased a “nice little affair” with another mystery A-lister.
She also played mum on “Call Her Daddy” in 2025 when describing a new man in her life “out of respect for his privacy.”
Handler said, “We didn’t really become lovers until about six or seven months ago. I invited him to Mallorca on a trip with a group of friends. … I’ve known him for years. I’ve always been attracted to him, but he was not available. I always have wanted someone like him in my life.”
