Chelsea Handler is once again making headlines with her signature unfiltered storytelling—this time, revealing juicy details about her past flirty exchanges with former New York Governor Andrew Cuomo, a topless photo that could have caused national chaos, and her unapologetic stance on threesomes.
Handler, never one to hold back, sat down for a revealing conversation on The Jamie Kern Lima Show, where she discussed her high-profile attraction to Cuomo during the pandemic, her experiences with multiple partners, and the wild story behind a risqué photo she sent to the ex-governor.
During the height of the COVID-19 pandemic, Cuomo’s daily press conferences made him an unlikely sex symbol for some, including Handler. On The View in 2020, she publicly declared her attraction to the then-governor, saying: "I would like to be penetrated by the Governor of New York."
Apparently, Cuomo took notice.
Handler claims Cuomo was “very flirtatious” after her declaration, eagerly soaking up the attention. She described the thrill of getting a voicemail from him—one she played for friends “probably a thousand times.”
"I can’t believe this is happening," Handler recalled thinking. "I’m going to become the First Lady of New York."
The two exchanged texts, made tentative plans for dinner, and seemed to be headed toward a real date—until Cuomo suddenly went silent.
"Once it became real and I was on the East Coast, I never heard from him again," Handler said, admitting she had been ghosted.
Determined to get some kind of reaction out of Cuomo, Handler sent him a bold parting message—a topless photo. But this wasn’t just any topless selfie.
"I was on a Vespa in Maine, wearing a face mask and a helmet—because you know, COVID safety," she recalled. "I had on a bikini, and I pulled the top down. My brother Roy was taking the picture."
Before she could send it, her sister Simone walked in on the bizarre photoshoot and yelled: "That is your brother!"
Handler admitted she didn’t care if the photo ended up on Cuomo’s phone—or even if it accidentally flashed on the big screen during one of his nationally televised COVID briefings.
"The thought that I could disrupt the country in that way and give everybody a little ounce of laughter—so I didn't care at that point," she laughed.
Cuomo never replied.
While the Cuomo crush ended in disappointment, Handler remains very open about her past adventures—including her experiences with threesomes.
Handler confirmed that she and her ex, television executive Ted Harbert, had "a lot" of threesomes during their relationship from 2006 to 2010.
"As long as you're in a trusting dynamic with your partner, bringing a third person in can be a lot of fun," she explained. "You have to trust each other. I'm definitely open to doing it again. It's kind of like drugs to me—I like adventure."
However, she made one thing clear: She has a strict "no two men" rule.
"I don't want to have sex with two men at the same time—that's not a fantasy of mine," she stated. "But I do like seeing a man that I'm with being sexual with another woman when it's in front of me. I find that very sexy."
She also revealed that she’d be open to a threesome with two women, adding, "Women are always safe."
But before the interview ended, she was asked the ultimate question—would she ever be in a relationship with another woman?
Before she could answer, the podcast cut off on a cliffhanger.
Whether it’s her failed fling with Cuomo, her unapologetic sex life, or her latest wild revelations, Handler continues to be one of the most outspoken and unpredictable voices in entertainment. And with her latest stories stirring up a media frenzy, fans are now left wondering—what will she say next?
