Chelsea Handler Details ‘Flirty’ Andrew Cuomo Texts, Opens Up About Past Threesomes with Ex

The comedian was a guest on The Jamie Kern Lima Show again this week, where talk turned to Handler professing her interested in Cuomo on The View in 2020, explaining at the time that his near-constant television presence in the early days of the coronavirus crisis was a turn on for her.

Lima asked how Cuomo responded to her, with Handler claiming he was “very flirtatious.”

“He ate it up. I went on The View and pronounced my declaration, I declared my attraction to him. I said, I would like to be penetrated by the Governor of New York,” she told Lima. “I got off the Zoom — it was during Covid — and like, now we wait. He will be in touch, I knew it. Three days went by and then I heard from him.”

“First he left a message, which I played probably 1,000 times,” she continued, saying that she unfortunately no longer has the recording, which she also played for her friends. “Then he called me on the phone, we talked one night … I can’t believe this is happening, I’m going to become the First Lady of New York, that’s how I was thinking about it.”

“He was very flirty, he liked it, I think he was getting a lot of attention at that time, probably from lots of other women, as well as me. We texted back and forth, it was cute,” she continued. “We set up a dinner date … so all of these things I thought were in progress, then once it became real and I was on the East Coast, I never heard from him again.”

She told Lima that she also sent some “very flirty pictures” his way, but was adamant he never sent any in return. One of the pictures she sent was topless, too, she said — explaining she sent it to him after she had already accepted that he had “ghosted” her.

“My sister is like, ‘Send him one more picture.’ I’m on a Vespa in Maine, I have a face mask on and a helmet, showing him how safe I am because of Covid,” she said. “I had a bikini on and I pulled the top down on my bikini and my brother Roy’s taking the picture of my and my sister Simone walks out and she’s like, ‘What are you doing? That is your brother!”

“The idea of a topless photo of Chelsea Handler somehow accidentally going through the governor’s phone and landing on one of those big screens during his early morning Covid briefings on CNN or FOX or MSNCB just brought so much joy to me,” Handler continued, “the thought 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 went on to clarify that their texts were never “sext-y,” but were “flirty” — saying he “was really enjoying the attention.”

During a 2020 appearance on The View, Cuomo also addressed their exchanges.

“I’ve had a lot of conversations about flattening the curve, but never quite that way,” Cuomo said. “I’m a big fan of Chelsea’s and she is great. We have fun.”

“But on my dating life — I’m only dating in-state residents,” he cracked. “I’m dating New York residents. If Chelsea changes her residence then maybe we can work it out.”

Elsewhere in the conversation, Handler was also asked about her apparent love of threesomes — after previously claiming she and ex Ted Harbert had “a lot of” them during their relationship from 2006-2010.

Speaking with Lima, she clarified that she has never had a foursome or fivesome, but finds the idea of a threesome, in general, “very sexy.”

“As long as you’re in a trusting dynamic with your partner, bringing a third person in, I think 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, so I’m always open to more adventure.”

When asked whether there was a specific dynamic necessary for her to feel comfortable — as in, the third being another man or a woman — she said the guest star “has to be a woman.”

“I don’t want to have sex with two men at the same time, I’m not interested in that, that’s not a fantasy of mine,” she explained. “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 added that she would be “into” having a threesome with two other women — saying, “Women are always safe” — before the podcast ended on a cliffhanger as she was asked whether she’s ever be in a relationship with another woman.

Watch the full interview above!