Comedian and television host Chelsea Handler has just returned from another whirlwind romantic escape with her new boyfriend, this time venturing to the historic city of Istanbul in Turkey. The 51-year-old entertainer, known for her sharp wit and candid humour, is keeping the identity of her mystery man private but has affectionately nicknamed him "Cowboy."
A Gambling Encounter in Las Vegas
Handler recently disclosed to the Las Vegas Review-Journal how she first encountered her beau last November at The Cosmopolitan of Las Vegas. "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," Handler recalled. "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."
The Critics Choice Awards host promptly repaid the loan, even adding an extra thousand dollars as interest, though she later reclaimed it, quipping, "I don't think he deserved that." This chance meeting at the gambling table sparked a connection that has since blossomed into a full-fledged romance.
From Antarctica to Istanbul
After their initial encounter, a mutual friend thought they looked "cute together" and passed Handler's phone number to Cowboy, who texted her the following morning. The relationship quickly escalated when Handler sent him a link to a luxury Insider Expeditions trip to Antarctica she had booked for Thanksgiving, and he joined her there.
"I'm still going strong with this guy. It's hot, and a woman like me needs a big move like that," the Ice Out activist declared. She added playfully, "He's downstairs getting a massage right now. He's my current Cowboy."
Exploring Istanbul During Ramadan
On Monday, Handler shared an Instagram slideshow featuring intimate moments with Cowboy as they explored Istanbul together to witness "what goes down during Ramadan." The Feeling producer-star, who boasts 18 million social media followers, captioned the post, "What a city."
She reflected on the cultural experience, writing, "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." This getaway marks just one of many international vacations the couple has enjoyed, having previously visited Finland, Jamaica, and Canada.
A History of High-Profile Relationships
Before Cowboy, Handler's romantic history includes relationships with comedian Jo Koy, chef Bobby Flay, hotelier André Balazs, rapper 50 Cent, comedian David Alan Grier, and former Comcast Entertainment Group CEO Ted Harbert. Her current romance appears to be thriving, with the couple frequently jet-setting across the globe.
Professional Endeavours and Touring
Beyond her personal life, Handler remains busy professionally. Last month, the Grammy-nominated funnywoman signed on to produce and portray a washed-up reality star in Zoe Young's comedy series Townhouse, which is in development with Hulu. She is also an influential figure with paid partnerships for brands such as Amp Fitness, Bella Coola Heli Sports, Grüns gummies, and Noble Mobile.
Handler's touring schedule continues unabated. She is next scheduled to bring her The High and Mighty Tour to Ohio's Playhouse Square State Theatre in Cleveland this Friday. Additionally, she will conclude her Chelsea at The Chelsea residency at The Cosmopolitan of Las Vegas on April 18 and May 30, bringing her full-circle to where she first met Cowboy.
The author of I'll Have What She's Having continues to balance a dynamic career with a passionate new romance, proving that love can indeed be a rewarding gamble.
