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Chelsea Handler eviscerates 'serious' actor she went on '...
Alexandra Bellusci · 2026-05-27 · via New York Post

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.”

Chelsea Handler and Kristin Cavallari discussing Handler's "unbearable date" on a podcast.

Chelsea Handler (pictured here on Kristin Cavallari’s podcast on Tuesday) opened up about an “unbearable” date she went on with an unnamed celebrity. YouTube/Let's Be Honest with Kristin Cavallari

Chelsea Handler speaking into a "Let's Be Honest" podcast microphone.

The comedian called the actor “so boring,” and claimed he only spoke about himself and his acting process. YouTube/Let's Be Honest with Kristin Cavallari

“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.”

Chelsea Handler speaking into a microphone with her hands open, sitting on a white sofa with cans of Fizzen Protein drink in the background.

The stand-up recalled, “He didn’t ask me one question about myself. I was like, ‘Oh, okay.'” YouTube/Let's Be Honest with Kristin Cavallari

Chelsea Handler being interviewed on a podcast, with a "Let's Be Honest" microphone in the foreground.

The author said her mystery man felt the date went great and she had to make up an excuse to jump ship. YouTube/Let's Be Honest with Kristin Cavallari

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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.'”

Chelsea Handler posing at The Abbey's 35th Anniversary Party.

The former talk show host (pictured here in May) also recounted one “nice little affair” she had with a fellow A-lister. Xavier Collin/Image Press Agency / BACKGRID

Chelsea Handler posing at the 31st Annual Critics Choice Awards.

The actress (pictured here in January) added that her dalliance only lasted a few months. Getty Images

“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.

Bobby Flay holding a plate of chicken with lime wedges and cilantro.

During her interview, Handler also called her dated with chef Bobby Flay (pictured here in May) “bad,” and claimed he stuck her with the bill. ABC via Getty Images

Chelsea Handler and Jo Koy pose together at the 64th Annual Grammy Awards.

The television personality was previously linked to Jo Koy (pictured here together in 2022) for less than a year before their 2022 split. Penske Media via Getty Images

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.

Chelsea Handler and Andre Balazs posing together.

The comic also dated businessman Andre Balazs (pictured here together in 2013) from 2011 until 2013. Donato Sardella

Ted Harbert in a suit and Chelsea Handler in a blue strapless gown on a red carpet.

Along with 50 Cent and Animal Planet star, Dave Salmoni, Handler also dated Comcast CEO Ted Harbert (pictured here together in 2008) for four years in the mid-2000s. Patrick McMullan via Getty Images

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.

Chelsea Handler and Joe Largura pose for a selfie, with Handler wearing a light blue head covering.

The producer recently debuted her new romance in March (as pictured here in an Instagram photo). chelseahandler/Instagram

Chelsea Handler and Joe Largura in the Basilica Cistern.

The “My Horizontal Life” author (pictured here with her new beau) only refers to her partner as “Cowboy.” chelseahandler/Instagram

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.