As far as romance is concerned in 2026, Chelsea Handler is deeply invested. Her weapon of choice? A blackjack table at The Cosmopolitan in Las Vegas—not Cupid’s bow.
The comedian, 51, has hard-launched her most intriguing relationship yet with a mysterious admirer she has dubbed “Cowboy”. However, fans eager for a name will have to wait; Handler is keeping the identity of her 37-year-old boyfriend private, though he has been identified as Joe Largura, a construction executive from Florida. But perhaps the most surprising detail of all is that this particular whirlwind romance began not with a swipe right, but with a high-risk gamble that required him to spot her a thousand dollars—a bet on love that is currently paying off in spades.
While her current flame is a mystery to the public, the dating history of the Chelsea Lately alum reads like a colorful, highly entertaining novel. From rap royalty to comedy peers, her list of former flames explains a lot about her current outlook on love and companionship.
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From 50 Cent to the “Cowboy”: A Timeline
Chelsea Handler has never been shy about her past. Her dating résumé includes a diverse mix of high-profile names. She famously had a short-lived but beloved romance with rapper 50 Cent back in 2011, whom she later affectionately referred to as her “favorite ex” for his fun-loving nature. She also dated fellow comedian Jo Koy for nearly a year before their split in 2022. Other notable names include chef Bobby Flay, hotelier André Balazs, and former E! executive Ted Harbert. Despite this long list, Handler has remained steadfastly unmarried, famously telling NBC that she isn’t sure she is “the marrying kind”.
Handler’s “type” has fluctuated wildly over the years, but one descriptor often associated with her love life is the question of dating Black men, specifically via her former relationship with 50 Cent and actor David Alan Grier. In a 2025 podcast appearance, Handler made headlines by explaining her preference for dating Black men, stating that she feels they “appreciate her more” for her sense of humor and directness compared to her previous experiences with white men. She even drew a parallel between her affinity for Black men and her decision to adopt a black Chow Chow dog, joking that she got the dog “because I like Black men … in my bed”.
While some fans viewed these remarks as complimentary, the comments also sparked online controversy, with some critics accusing her of stereotyping or fetishizing Black men based solely on physical or cultural attributes.
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Chelsea Handler: The Gambler’s Guide to Dating
Handler’s past might be complicated, but her present is surprisingly linear: it involves borrowing money at a casino and flying to Antarctica. The story of her 2026 romance is so cinematic that it feels scripted.
In November 2025, Handler was on a losing streak at a blackjack table when she spotted “Cowboy” seated nearby. “I was like, ‘Hey, buddy, can I borrow $1,000? I’m gonna start winning right away. And he was like, ‘Yeah, absolutely!'” she told the Las Vegas Review-Journal. She won the hand and paid him back immediately. Unbeknownst to her, a friend slipped him her number. The next morning, she received a text that simply read: “I had so much fun last night with you”.
From there, the relationship escalated at lightning speed. Handler had a solo trip booked for Antarctica, so she sent him the itinerary. His response? “I’ll see you there”. He did, and they have been globetrotting ever since—visiting Jamaica, Finland, and Turkey within the span of weeks. “It’s hot, and a woman like me needs a big move like that,” Handler quipped. For now, the comedian who once swore off serious relationships seems to have finally met her match, even if he is just the man she met when she was short on cash.
