Chelsea Handler eviscerates ‘serious’ actor she went on ‘unbearable’ date with, teases ‘nice little affair’ with A-lister

Chelsea Handler’s horizontal life includes a few secret A-listers.

The comedian got candid about an “unbearable” date she once went on with an unnamed celebrity.

“He was so boring. But I can’t tell you the name. I just can’t,” Handler, 51, teased while on Tuesday’s episode of Kristin Cavallari’s “Let’s Be Honest” podcast.

The stand-up explained that she made the first move, but her mystery man was “receptive.”

“We went on a date and it was unbearable. And I worked hard,” Handler confessed. “He was so serious about himself as an actor.”

Calling her courter “so boring,” the author added that “he was talking about acting in a way I can’t take seriously.”

Not being an actress herself, but an “entertainer,” Handler couldn’t believe how self-obsessed her date was.

“He didn’t ask me one question about myself,” she recounted. “I was like, ‘Oh, okay.’”

However, the pair had a different version of events — with the actor thinking the night went “great.”

Handler and her potential suitor, meanwhile, met in America but went out together in a different country.

“I had really gone out of my way. I was on my way somewhere and I stopped for the night in a city to go on a date with this guy,” the “Chelsea Lately” alum admitted.

Handler said she felt like a woman in her 20s who had to come up with a lie to escape the disastrous evening.

“I had really pursued him, but once I sat down with him, I was like, ‘You’re so boring and so annoying.’”

“That’s what’s wrong with men,” Handler stated. “He was very much about himself, and his process and his acting.”

The comic was hoping the two could take the conversation to a lighter place, but the moment never arose.

Meanwhile, without naming names — for a second time — Handler also told Cavallari, 39, she had “a nice little affair” with one major celeb.

“That wasn’t even long term. It was a few months,” she continued.

However, Handler didn’t shy away from dropping one known moniker.

She called her night out with Bobby Flay: “Just bad.”

Handler claimed that the chef, 61, ordered room service but stuck her with the bill.

The duo tried going out once more, but according to Handler, “It was just like, messy.”

Handler’s confessions come a few years after her breakup from fellow comedian Jo Koy.

The former flames dated for less than a year before calling it quits in 2022.

Handler previously dated Comcast CEO Ted Harbert for four years from 2006 until 2010.

That same year, she struck up a romance with Animal Planet star Dave Salmoni.

Handler was also briefly linked to 50 Cent, whom she’s dubbed her “favorite ex,” in 2011.

The talk show host and businessman Andre Balazs were romantically linked between 2011 and 2013.

In March, Handler debuted her new romance with a mystery man she calls “Cowboy,” on Instagram.

The carousel included pictures from the couple’s trip to Istanbul in Turkey.