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Tori Spelling details very unusual date with Charlie Sheen


Tori Spelling, the Beverly Hills 90210 actress turned podcast host, recalled an unusual date and her overall memories with Charlie Sheen.


Tori Spelling and Charlie Sheen© Getty Images
Tess Hill
Tess HillNews and Features Writer
September 23, 2025
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Tori Spelling confirmed to her podcast listeners yesterday that in the late '90s, she and Charlie Sheen dated. News of their connection came when the Two and a Half Men actor mentioned Tori's name in his new memoir, The Book of Sheen. While their interaction was brief, the Beverly Hills 90210 actress shared memories of their date on her misSPELLING podcast. Tori, 52, remembered being set up by a mutual friend, Kevin, who she called her "best friend since we were 15." 

"[When] we lived both at the Wilshire, there was a time that Kevin was friends with him when they were both sober — were trying to be sober — and Kevin said, 'Charlie wants to ask you on a date,'" Tori recalled. She remembered feeling "nervous," so she decided instead to go on an usual date with Charlie.

Tori Spelling and Dean Mcdermott attend Luskin Orthopedic Institute For Children Gala at Universal Studios Hollywood on June 10, 2023 in Universal City, California© Getty Images
Tori went on to marry Dean Mcdermott, who she was with until 2024.

Tori explained that she organized the date so that Kevin and his parents attended too. "We were just getting to know each other," Tori said. "It wasn't a quote-unquote date, but it was like — they were trying to set us up." The actress remembered Charlie as "unimaginably intelligent" and "charming, smart, funny, witty."

While she remembered several "good moments" shared with Charlie, she also highlighted moments tainted by his addiction struggles. Tori remembered: "And then the bad moment is when I get the call [from Kevin], 'Come downstairs. Charlie's having this party. You have to come here, please.'" She recalled seeing Charlie "holding some apparatus" that he later revealed was a "crack pipe."

Tori Spelling and Shannen Doherty© Getty Images
Tori rose to fame at 17 on Beverly Hills 90210

"I thought he was kidding! And I was like, haha, funny," Tori said. The actress admitted she was scared of the "gnarly" scene inside his condo, where "it was dark and there were bodies everywhere." Tori remembered responding to Charlie's offer with a "no thanks." Charlie reportedly answered: "Well, what would you like? We have every drug.'"

Her memories of Charlie only became a bit messier. On the podcast, she told listeners of the time he was wanted by the U.S. Marshals. "I was standing in my laundry room and Kevin comes in and says, 'T, I need to ask you a favor.' And I was like, 'Yeah, of course, anything.' And he's like, ‘Can we hide Charlie?'"

tori spelling and her children© Chelsea Lauren/Shutterstock
Tori is a mom-of-five kids

The actress remembered thinking: "[I] knew what was happening in the news, and this was bad news. And [I would be] an accomplice." Tori recalled: "I said, 'Are you [expletive] kidding me? No, I'm not doing that.' He's like, 'T, you don't understand. They're gonna arrest him. They're gonna take him away.' And I was like, 'I'm sorry. I think [Charlie's] a really great guy. I like him, but I can't do this.'"

Denise Richards and Charlie Sheen during 2003-2004 CBS Upfront - After Party at Tavern on the Green in New York City, New York, United States© Getty Images
Charlie was married to Denise Richards for four years

Charlie also remembered this moment in his memoir. He wrote: "[Kevin] explained that Tori felt bad for me but viewed my situation as radioactive and didn't wanna go anywhere near it. (Couldn't blame her, I suppose, but [expletive] man, who knows what story I'd be bangin' out right now if the heir to daddy's throne had said yes?)"

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