Tori Spelling reveals she agreed to go on a date with Charlie Sheen under one condition

I was so surprised to hear this on Tori Spelling’s podcast, misSPELLING! She shared that she actually dated Charlie Sheen for a little while, but she only said yes if he met a very specific requirement she had.

On Monday’s podcast, Tori revealed that her friend and dentist, Kevin, used to be friends with someone they were both trying to get sober with. Kevin told Tori that this person, Charlie, was interested in going on a date with her.

Oh my gosh, she finally agreed to a date! But it wasn’t *quite* the perfect one-on-one I’d imagined. Apparently, she was really nervous and didn’t want to go by herself, which, honestly, is so relatable! So, she ended up going with Charlie, and Kevin and his parents tagged along too – they all went to this Italian place. It wasn’t ideal, but at least she went *with* him!

The actress explained that despite a lack of romantic connection, Charlie Sheen was incredibly intelligent.

The 52-year-old actress, known for her role on Beverly Hills, 90210, remembered the 60-year-old actor as being ‘extremely bright’.

This story follows closely after the release of Charlie Sheen’s memoir, *The Life of Sheen*, and the premiere of the Netflix documentary about him.

She emphasized, ‘And his humor! Talk about charming, smart, funny, witty. This guy was it.’ 

During the show, Tori discussed a story from a famous actor’s book about a time he had to go into hiding to avoid the police after a legal issue.

Tori recounted that she was in her laundry room when Kevin walked in and asked her for a favor: could they hide Charlie?

This is terrible. They’re searching for him with helicopters and everything. I’m even wondering if I should hide him.

She decided to stay out of it, and the actor later reflected in his memoir that he understood her choice. He wondered, though, how different his life might be if the wealthy heir had agreed to help him.

The pages of the Hollywood vet’s memoir are full of scandalous confessions.

But the father-of-five has since turned his life around.

In an interview with Page Six he said he’s been sober for eight years, and is also celibate. 

In his book, he shared how his 21-year-old daughter, Sami, helped him get sober, describing the specific moment he realized he needed to stop drinking.

On December 10, 2017, I was already on my third coffee with a splash of Macallan whisky by 9:00 AM. That’s when my daughter, Sam, called to ask when we were planning to leave.

I completely forgot about her appointment that day. I’ve always been careful to keep things separate, so when I messed up, I called Tony T. – he’d been in similar predicaments before and was happy to help.

Besides Sami, the actor also has a 20-year-old daughter named Lola Sheen with Richards.

He has four children: 16-year-old twins Bob and Max Sheen with his ex-wife Brooke Mueller, and a 40-year-old daughter, Cassandra Estevez, with a former high school girlfriend, Paula Profit.

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2025-09-23 20:18