Chelsea Handler in new relationship with mystery man she borrowed $1,000 from in Vegas
Published in Entertainment News
Chelsea Handler is in a new relationship with a mystery man she borrowed $1,000 from at a blackjack table.
The US comedian and television host, 51, described the incident in a new interview, revealing how the chance encounter has since turned into a globe-trotting romance, but refused to identify her new boyfriend.
While discussing her return to her comedy residency at The Chelsea theatre at The Cosmopolitan in Sin City, Chelsea told the Las Vegas Review-Journal the relationship began after she asked a man wearing a cowboy hat to lend her money during a night gambling at the casino.
She said: "I picked up a gambling habit. Every month, when I perform, I always have a group of friends that come out, randos from all over the world.
"I am basically forcing them to gamble with me."
Chelsea explained blackjack is her preferred casino game and said the incident happened during a previous stay while she was trying to recover losses at the table.
She added: "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.
"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."
Chelsea said she repaid the money the same evening after winning.
She added: "I paid him back another thousand just for interest, which I ended up taking back at the end of the night because it said, 'I don't think he deserved that.'"
Chelsea declined to reveal the man's identity but said she refers to him as her "Cowboy".
She also said the pair later reconnected after the man sent her a message the following day.
Chelsea added a friend had shared her number with him after noticing the pair's interaction at the casino table.
She said: "I'm like, 'Who is texting me? And my friend says, 'Oh, that's the cowboy from the blackjack table. I gave him your number because you guys were so cute together.'"
Chelsea said the relationship quickly developed when she invited him to join her on a trip.
She went on: "I sent him a link to this trip I went on in Antarctica, and then he bought a ticket and met me there."
Chelsea said the relationship is still continuing, adding: "I'm still going strong with this guy. It's hot, and a woman like me needs a big move like that."
The performer is scheduled to perform at the venue as part of a monthly run and is also launching her High and Mighty US tour.
But she said the story will not form part of her stand-up routine.
Chelsea added: "That's a personal story. I don't talk about it on the stage, only to reporters."
Chelsea began her residency at The Chelsea venue in September 2024 after being approached by Live Nation Las Vegas. She is the theatre's first female comic resident headliner.
Chelsea is also working on a Hulu series titled Townhouse.












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