Chelsea Handler Spills The Tea On Awkward Celeb Date And Secret A-List Affair

Chelsea Handler Unmasks Awkward Date with Mystery Actor

Chelsea Handler is not holding back when it comes to her love life escapades. On a recent episode of Kristin Cavallari’s "Let’s Be Honest" podcast, the comedian opened up about a date that was nothing short of "unbearable." While she kept the actor's identity under wraps, she didn't shy away from describing the evening as "so boring" – thanks to her date's obsession with his acting career.

Handler, 51, shared her frustration, stating, "He was talking about acting in a way I can’t take seriously." Despite her efforts to make the date work, the actor's self-centeredness left her unimpressed. "He didn’t ask me one question about myself," she recounted, adding a touch of humor to the otherwise painful memory.

“He was very much about himself, and his process and his acting.”

The evening took place in an unexpected setting, as Handler revealed she had gone out of her way to meet the actor in a different country. Despite the effort, she ended up concocting an excuse to escape the night.

Secret Affair with a Major A-Lister

Handler also hinted at a "nice little affair" with a well-known A-lister, keeping fans on their toes by withholding names yet again. This fling, she mentioned, was brief, lasting only a few months.

The stand-up comedian has had her fair share of celebrity romances. She humorously recalled a "bad" date with chef Bobby Flay, where she claimed he stuck her with the bill after ordering room service. Though they attempted a second date, it was "just like, messy," according to Handler.

From Past to Present: Handler’s Love Life

Handler’s dating history is as colorful as her comedy. She was romantically linked to Jo Koy, with whom she split in 2022 after less than a year. Other past flames include Comcast CEO Ted Harbert, Animal Planet star Dave Salmoni, and businessman Andre Balazs.

In March, Handler introduced her Instagram followers to her new mystery man, affectionately dubbed "Cowboy," as they enjoyed a getaway to Istanbul, Turkey. She also affectionately refers to rapper 50 Cent as her "favorite ex," with whom she had a brief romance in 2011.

With a history as intriguing as her stand-up, Chelsea Handler continues to keep her fans entertained both on and off the stage.