Chelsea Handler met new lover at the Vegas Blackjack table
Chelsea Handler is in a new relationship with a mystery man from whom she borrowed a thousand dollars at a blackjack table – and RadarOnline.com can reveal that the romance has caused major concerns in her inner circle.
The American comedian and television host, 51, detailed the incident in a new interview and revealed how the chance encounter has since turned into a globe-trotting romance, but declined to identify her new boyfriend.
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Chelsea Handler revealed she started dating a mystery man after meeting at the blackjack table.
Discussing her return to her comedy residency at The Chelsea Theater at The Cosmopolitan in Sin City, Handler said the relationship began after she asked a man in a cowboy hat to lend her money during a night of gambling at the casino.
Handler added, “I’ve developed a gambling habit. Every month, when I perform, I always have a group of friends who come out, randos from all over the world. I basically force them to gamble with me.”
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Comedian asked stranger for $1,000 at blackjack table
Handler asked the stranger for a loan of $1,000 during the game.
She went on to explain that blackjack is her favorite casino game and said the incident occurred during a previous stay while she was trying to recover her losses at the table.
Handler said, “I had to ask this guy sitting at a blackjack table 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 going to start winning right away.’
“And he said, ‘Yes, absolutely!’ So he gave me $1,000.”
Handler insisted she refund the money the same night after winning.
She said, “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.'”
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‘Cowboy’
She jokingly calls the mysterious boyfriend “Cowboy.”
Handler declined to reveal the man’s identity, but said she called him her “Cowboy.”
She also said the pair later reconnected after the man messaged her the next day.
Handler added that a friend shared her number with him after noticing the couple’s interaction at the casino table.
She said, “I’m like, ‘Who’s texting me? And my friend’s like, ‘Oh, that’s the cowboy from the blackjack table. I gave him your number because you guys were so cute together.'”
Handler said the relationship developed quickly when she invited him to join her on the trip.
She continued, “I sent him a link to the trip I took to Antarctica, and then he bought a ticket and met me there.”
Chelsea said of the relationship: “I still feel strong with this man. It’s hot, and a woman like me needs such a big step.”
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Friends are reportedly concerned about the Vegas lifestyle
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Handler continues her comedy residency and US tour in Las Vegas.
But a source said: ‘Chelsea may seem happy but the way she describes meeting her new man has raised major red flags among her friends.
‘It all sounds vague. They ask what kind of guy just borrows $1,000 with no questions asked.
“They are also concerned that Chelsea will go down a very wild path in Vegas.”
The artist will 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 won’t be part of her stand-up routine.
Handler added, “That’s a personal story. I don’t talk about it on stage, only with reporters.”
The comic began her residency at The Chelsea in September 2024 after being approached by Live Nation Las Vegas.
She is the theater’s first female headliner and is also working on a Hulu series called Townhouse.
