Tori Spelling was close to having herself more than half a man in Charlie Sheen.
The 90210 alum recalled a time when she and the Two and a Half Men star were set up on a date by her best friend Kevin, who was Tori’s roommate and Charlie’s buddy in the 1990s.
“There was a time that Kevin was friends with him when they were both sober—were trying to be sober,” Tori—who lived in the same Los Angeles high-rise as Kevin and Charlie—shared on the Sept. 22 episode of her misSPELLING podcast. “And Kevin said, ‘Charlie wants to ask you on a date.’”
The 52-year-old admitted that she was nervous about the prospect and didn’t want to go alone, at which point Kevin mentioned that he would be going to dinner with his parents at an Italian restaurant in Beverly Hills.
“Charlie and I both knew his parents,” Tori explained. “So it was Kevin’s parents, me, Kevin and Charlie, and we went out to dinner.”
And while going out on a date with your friend’s parents might be an interesting choice for most, Tori insisted that she and Charlie “were just getting to know each other,” and despite Kevin’s efforts to set them up, it wasn’t really a date.
But it was during that outing that Tori realized just how “unimaginably intelligent” Charlie was.
“Off the charts,” she gushed. “And his humor.”
The podcaster added, “Talk about charming, smart, funny, witty. This guy was it.”
And the duo’s relationship continued to evolve in interesting ways, as Tori—who shares kids Liam, 18, Stella, 17, Hattie, 13, Finn, 13, and Beau, 8, with ex DeanMcDermott—recalled being invited to a party one night at Charlie’s condo.
According to Tori, she and her friends walked in and Charlie was “holding some apparatus,” which he allegedly held out to her, asking if she wanted to take a hit of a “crack pipe.”
The So Notorious actress quickly said no, adding that it felt like a “gnarly” scene inside his home and that “it was dark and there were bodies everywhere.”
Tori also addressed the mention of her in Charlie’s recently released memoir The Book of Sheen, where the 60-year-old recalls asking if Tori and Kevin could hide him in their condo when there was a warrant out for his arrest.
Tori added a bit more color to the story, saying, “I’m 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?’”
And while she didn’t know the full extent of what was happening, she knew it was “bad news” and there was a chance she could be considered “an accomplice.”
“I said, ‘Are you f–king kidding me? No, I’m not doing that,’” she shared. “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 he’s a really great guy. I like him. But I can’t do this.'”
As Charlie wrote in his book, he was told that “Tori felt bad for me but viewed my situation as radioactive and didn’t wanna go anywhere near it.”
He added, “Couldn’t blame her, I suppose, but s–t man, who knows what story I’d be bangin’ out right now if the heir to daddy’s throne had said yes?”
For more of Charlie’s most intense moments, keep reading.
Did Charlie Sheen Really Shoot Kelly Preston?
The prevailing narrative for years was that Charlie Sheen accidentally shot then-girlfriend Kelly Preston in the arm when the two were living together in 1990. The evidence? Preston had a wound and Sheen was…well, he was who he was.
But that wasn’t really the case.
“It was an accident,” Preston, who died in 2020, told TMZ in 2011 when approached amid a spate of fresh headlines about her ex’s behavior. “He had put [the gun] in his pocket and it fell out and it went off.”
And according to Sheen, he wasn’t even in the room.
“I was downstairs early in the morning making coffee and I thought she was still asleep upstairs,” Sheen said in 2016 during a Vancouver stop on his My Violent Torpedo of Truth Tour. “And I heard a f–king gunshot go off.”
What Preston told him, Sheen continued, was that “the tiny revolver I used to carry…it fell out of the back jeans pocket and hit the floor and shot a bullet right between her legs. So, she got hit with shrapnel from the toilet bowl.”
Charlie Sheen Admitted to Spending $50,000 on Escorts
When Hollywood madam Heidi Fleiss was on trial in June 1995, accused (and subsequently convicted) of tax evasion and money laundering, Sheen was revealed as one of her most high-profile clients.
In video testimony played in court, per the Los Angeles Times, Sheen said that he spent more than $50,000 on “sexual services,” utilizing Fleiss’ business to order escorts 27 times and also contacting “Heidi girls” directly at least 20 times.
“I apologize to my family, my future wife, my close friends, for any embarrassment these incidents may have caused,” Sheen, who was engaged to Donna Peele at the time, said in a statement through his rep. “I offer no other explanation for my actions, only the truth, which is contained in detail within my testimony. They wouldn’t call it ‘the past’ if it wasn’t.”
He and Peel tied the knot in September 1995 and divorced the following year.
Charlie Sheen Arrested for Allegedly Assaulting Brittany Ashland
Brittany Ashland accused the actor of grabbing her hair and pushing her to the floor, rendering her unconscious, at his L.A.-area home in December 1996.
Sheen pleaded no contest to misdemeanor battery in June 1997 and was given a one-year suspended jail term, plus two years’ probation.
“I feel this is very fair, and I’m grateful,” the Hot Shots star told Malibu Municipal Court Judge Lawrence Mira at the time. “You will not see me back in this courtroom.”
Charlie Sheen’s Dad Martin Sheen Laid Down the Law After Overdose
In May 1998, Sheen was hospitalized for a cocaine overdose—which was brought to authorities’ attention by his father, The West Wing star Martin Sheen. A judge found Sheen to be in violation of his probation from his 1997 assault plea and ordered him into a drug rehabilitation program.
“In paying the bill, I got to see why he was in there,” Martin told AARP The Magazinein 2008. “He’d consumed an illegal substance; he was on probation…This was a criminal matter. And so that was the wedge; that was the leverage I had. That is what I took to the court; that’s what I took to the sheriff. It was the only way I got him.”
At the time, “It felt like the biggest betrayal you could possibly endure,” Sheen said in a September 2025 Good Morning America interview ahead of the premiere of his warts-and-all Netflix documentary aka Charlie Sheen and memoir The Book of Sheen.
Eventually, he “saw it as love,” the Major League actor continued. “But in the moment, it’s like, in the book when my bodyguard comes to the bedroom door and he says, ‘You know, the US Marshals are on the way. We’re leaving in five.'”
Charlie Sheen’s Messy Custody Battle With Ex-Wife Denise Richards
Sheen married Denise Richards on June 15, 2002. Their daughter Sami Sheen was born March 4, 2004, and LolaSheen arrived on June 1, 2005—three months after Richards filed for divorce.
They briefly reconciled, but by early 2006 the split was back on.
In filing for a temporary restraining order that April, Richards alleged Sheen had pushed and threatened to kill her.
Sheen denied the accusations, but a judge ordered him to stay 300 feet away from her and their daughters—except during supervised visits—for the time being.
“Obviously, what has taken place is vile, is unconscionable, is without merit, is a transparent and immature smear campaign,” Sheen said in a statement, per ABC News. “[Richards is] claiming certain things. It’s baseless.”
They reached a custody arrangement that May and a judge signed off on their divorce six months later, but—while they’re friendly now—they were in and out of court for years, and Richards was the target of more than a few of Sheen’s infamous Twitter tirades.
Charlie Sheen Arrested for Assaulting Brooke Mueller on Christmas
Sheen married real estate investor Brooke Mueller on May 30, 2008, and they welcomed twin sons Bob and Max in March 2009.
On Dec. 25, 2009, Sheen was arrested in Aspen, Colo., on domestic violence-related charges for allegedly assaulting his wife, who told police that the actor held a knife to her throat and said, “You better be in fear.”
Both spouses checked into rehab afterward. Sheen pleaded guilty in August 2010 to a reduced charge of misdemeanor assault and was allowed to return to treatment instead of go to jail.
He said in a statement, “I look forward to complying with the court’s decision, getting on with my life and putting this behind me.”
Charlie Sheen Hospitalized After Plaza Hotel Disturbance
Sheen was hospitalized in October 2010 for what his rep said was an “adverse reaction” to medication after cops were called to the Plaza Hotel in New York to respond to, per their report, an “emotionally disturbed individual.” Richards and their daughters were staying at the hotel in a separate suite, and porn actress Capri Anderson was in Sheen’s room at the time.
He and Mueller both filed for divorce on Nov. 1, with Sheen citing their date of separation as the day of their Aspen altercation. Their split was finalized in 2011.
Charlie Sheen Fired From Two and a Half Men
It’s hard to encapsulate just how bizarre Sheen’s 2011 war of words with Two and a Half Men creator Chuck Lorre was—but ultimately the four-time Emmy nominee was fired from the hit CBS show after seven seasons.
Sheen’s subsequent lawsuit against Warner Bros. seeking $100 million for alleged wrongful termination was settled that September for a reported $25 million.
Reflecting on that tumultuous chapter in which he ranted about the “tiger blood” coursing through his veins and the “goddesses” he was keeping company with, Sheen concluded a decade later that he wasn’t “#winning” after all.
“People have [said to] me, ‘Hey, man, that was so cool, that was so fun to watch,” he told Yahoo! Entertainment in 2021. “That was so cool to be a part of and support and all that energy and, you know, we stuck it to the man. My thought behind that is, ‘Oh, yeah, great. I’m so glad that I traded early retirement for a f–king hashtag.'”
Charlie Sheen Reveals HIV-Positive Status
Sheen shared on Today in November 2015 that he found out “roughly four years ago” that he was HIV-positive.
“I was so depressed by the condition that I was in,” he recalled. “I was doing a lot of drugs. I was drinking way too much. I was making really bad decisions. That part I own, 100 percent.”
Sheen said he had paid people who demanded money for their silence “enough to where it has depleted the future.”
So, in confirming his status, he hoped to “release myself from this prison.”
Sami Sheen Says She Doesn’t Talk to Dad Charlie Sheen
Though she chose to live with her dad in 2021, Sami said in April 2025 that she hadn’t talked to Sheen in a year or texted with him for six months.
He started sending her “some crazy stuff,” she said on Gia Giudice’s Casual Chaos podcast, and “I’ve had him blocked for a minute now. I had to put a stop to it and tell him, ‘Do not contact me ever again because this is crazy.’”
Sheen said on GMA in September 2025 that “there’s always a shot for a better tomorrow” as far as reconciling goes, but “I don’t really know what I did, that’s the problem. I don’t know what I’m supposed to apologize for.”
But, the actor is confident that “this is not a forever thing. Her and I will work it out. We have a history of that that’s too valuable to let some moment destroy all of that.”
