Love is in the air again for Chelsea Handler.
The comedian, who previously dated Ted Harbert and Jo Koy, is dating a mystery man she met at a Las Vegas blackjack table in November 2025. While she has not publicly revealed her boyfriend’s identity, she detailed how their paths crossed at The Cosmopolitan hotel and casino.
“I had to ask this guy sitting at a blackjack table who was wearing a cowboy hat, he had a lot of chips, like, thousands of dollars,” she told the Las Vegas Review-Journal. “I was like, ‘Hey, buddy, can I borrow $1,000? I’m gonna start winning right away. And he was like, ‘Yeah, absolutely!’ So he gave me $1,000.”
Handler paid the man back “another thousand just for interest” when she won immediately, adding, “Which I ended up taking back at the end of the night because I said, ‘I don’t think he deserved that.'”
Her friend, who was with her at the time, reportedly gave him her number without Handler’s knowledge. He texted her the next morning — and the rest is history.
In the same interview, Handler revealed her boyfriend is her “current Cowboy.”
“He’s not a real cowboy,” she clarified to the Las Vegas Review-Journal. “but I call him Cowboy.”
The exact date their relationship began remains unknown, but Handler and her boyfriend have traveled together since the start of their romance.
In fact, she invited him to Antarctica for Thanksgiving just weeks after their November 2025 meeting.
“I sent him a link to this trip I went on in Antarctica, and then he bought a ticket and met me there,” she told the outlet. “I’m still going strong with this guy. It’s hot, and a woman like me needs a big move like that.”
He then joined her to a trip to Finland to celebrate her birthday in February.
Handler captioned a carousel from the vacation, “I decided it was time to remind myself of some of the natural beauty in this world, so I swung by Finland for some northern light and igloo action.”
Then, on March 9, the Chelsea Lately host uploaded snaps from their Istanbul getaway.
She wrote, “I swung by Istanbul after Finland to check out what goes down during Ramadan. What a city. If I retained 50% of what I learned about the Byzantine, Ottoman, and Arabian Empires, I am much more knowledgeable than when I left.”
“What a gorgeous, history-filled trip with a nice injection of my signature nonsense. See you in Cleveland, Columbus and Cincinnati this weekend. I like to get around,” she added in the caption.