Chelsea Handler Dishes Juicy Details On 'Unbearable' Date With A-List Actor

Chelsea Handler Holds Nothing Back

Chelsea Handler is back at it, serving up sizzling stories from her encounters with Hollywood's elite. During a candid chat on Kristin Cavallari's "Let's Be Honest" podcast, the sharp-tongued comedian, 51, revealed she once went on a date with a top-tier actor who, she says, was a total snooze-fest.

Handler didn't shy away from calling the date "unbearable," despite her initial interest. "We were flirting, and then I made the move," she said. "So I made the move, and he was receptive, and we were hanging out, and I saw him, and we went on a date, and it was unbearable. And I worked hard." The unnamed actor, it seems, couldn’t stop going on about himself and his craft in a way Handler found insufferable.

“Immediately I was like you're so boring and you're so annoying – like anyone who talks about themselves for that long on a date is just that's exactly what's wrong with men.”

A Peek Behind the Curtain

Handler painted a picture of an actor so absorbed in his process that he never even bothered to ask about her. "He was very much about himself and his process and his acting," she explained, noting that she left the date feeling deeply disappointed.

But that wasn't the only tea she spilled. Handler teased a "nice little affair" with another celebrity—a star she still keeps under wraps.

Handler’s Take on Modern Romance

It's not just her own experiences that Handler is dishing on. In a separate podcast appearance on "Howie Mandel Does Stuff," she took aim at the modern dating scene, describing it as a tough landscape for straight women. "It’s very hard in today’s world to meet straight guys that have their s--- together," she noted.

Handler’s philosophy on love and relationships is decidedly independent. While she was previously linked with comedian Jo Koy, their year-long romance ended in 2022. Now, she embraces a lifestyle that prioritizes freedom over traditional commitments like marriage, which she calls "outdated."

As she told the "Angie Martinez IRL Podcast," "I'm here for women, and I'm here for myself. I've never been very thirsty for a man or a partner. You've got to really kind of get my attention for me to pay attention in a serious way, because otherwise it's a bunch of casual encounters." Handler clearly values her independence, enjoying travel and casual flings over more serious relationships.