Tori Spelling Details Past Date With Charlie Sheen

Tori Spelling was close to having herself more than half a man in Charlie Sheen.

The former 90210 actress remembered being set up on a date with the Two and a Half Men star by a mutual friend named Kevin. Kevin was Tori’s roommate and Charlie’s friend back in the 1990s.

Tori, a resident of the same Los Angeles building as Kevin and Charlie, revealed on her September 22nd podcast, misSPELLING, that Kevin and Charlie were once friends while both were trying to stay sober. She said Kevin told her that Charlie was interested in going on a date with her.

The woman, 52, confessed she felt anxious about it and didn’t want to go by herself. Just then, Kevin said he was having dinner with his parents at an Italian restaurant in Beverly Hills.

Tori explained that she and Charlie were both acquainted with Kevin’s parents. The group – Kevin’s parents, Tori, Kevin, and Charlie – all went out to dinner together.

Although some might find it unusual, Tori explained that she and Charlie were simply becoming better acquainted, and despite Kevin trying to play matchmaker, it wasn’t a real 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.”

Tori and her partner’s relationship kept changing, and Tori-who has five children with her ex-husband, Dean McDermott-remembered being invited to a party at Charlie’s apartment one evening. Her children are Liam, 18, Stella, 17, Hattie and Finn, both 13, and Beau, 8.

Tori said that when she and her friends entered, Charlie was holding something, and he supposedly offered it to her, asking if she wanted to smoke from a crack pipe.

The famous actress immediately refused, describing the scene inside his house as disturbing and chaotic. She said it was dark and full of people, giving her a bad feeling.

Tori Spelling recently responded to a story in Charlie Sheen’s new memoir, The Book of Sheen. In the book, Sheen, age 60, writes about asking Tori and her husband, Kevin, if he could hide at their apartment to avoid being arrested when there was a warrant out for him.

Tori explained that she was in her laundry room when Kevin walked in and asked for a favor. He asked if they could hide Charlie, and Tori immediately said yes, offering to do anything he needed.

Honestly, I could feel something wasn’t right, even if I didn’t know all the details. It felt like really bad news, and I worried I might get dragged into it, potentially seen as someone who helped it happen, even unintentionally.

She recounted saying, ‘Are you serious? I absolutely won’t do that.’ He then explained that he was in serious trouble and could be arrested. Despite feeling positively about him, she firmly replied, ‘I’m sorry, but I can’t help with this.’

In his book, Charlie recalled being told that Tori sympathized with him, but considered his problems too difficult or damaging to get involved with.

He admitted he understood her decision, but wondered what his life would be like now if she, the daughter of a powerful man, had accepted him. He speculated he’d be telling a very different story.

For more of Charlie’s most intense moments, keep reading.

For a long time, the story going around was that Charlie Sheen unintentionally shot his then-girlfriend, Kelly Preston, in the arm back in 1990 while they were living together. The supposed proof? Preston had a gunshot wound, and Sheen had a reputation for being unpredictable.

But that wasn’t really the case.

In 2011, Preston, who passed away in 2020, explained to TMZ that the incident was an accident. She said her ex-husband had put the gun in his pocket, it slipped out, and then fired.

And according to Sheen, he wasn’t even in the room.

In 2016, while making coffee early one morning, Sheen said he thought his wife was still sleeping upstairs. He was shocked when he heard a gunshot, as he recalled during a stop on his My Violent Torpedo of Truth Tour in Vancouver.

You won’t believe what Preston told me, and I just have to share it. Apparently, my little revolver – the one I used to carry in my back jeans pocket – slipped out and fell. It actually went off, and the bullet somehow went right between her legs. The crazy part? She ended up getting hit with pieces of the shattered toilet bowl! It’s just… unbelievable.

During Heidi Fleiss’s 1995 trial for tax evasion and money laundering – charges she was ultimately found guilty of – it was revealed that actor Charlie Sheen was one of her most famous clients.

According to testimony shown in court, as reported by the Los Angeles Times, Charlie Sheen admitted to spending over $50,000 on escorts. He used Fleiss’ service to book them 27 times and contacted escorts directly, known as “Heidi girls,” at least 20 times.

Charlie Sheen apologized to his family, his then-fiancée Donna Peele, and his friends for any shame his recent actions may have brought them. He stated he wouldn’t offer excuses, and that his full account of what happened was already given in his testimony, adding that the situation is now in the past.

He and Peel tied the knot in September 1995 and divorced the following year.

In December 1996, Brittany Ashland alleged that the actor assaulted her at his home near Los Angeles, claiming he grabbed her hair, pushed her to the floor, and caused her to lose consciousness.

In June 1997, Charlie Sheen accepted a plea deal for a misdemeanor battery charge, resulting in a one-year suspended jail sentence and two years of probation.

The *Hot Shots* actor told Judge Lawrence Mira in court that he thought the outcome was fair and he appreciated it, adding that he wouldn’t be appearing in that courtroom again.

In May 1998, Charlie Sheen was hospitalized after overdosing on cocaine. His father, Martin Sheen, who starred in *The West Wing*, alerted the authorities. The judge determined Sheen had violated his probation from a previous assault conviction and required him to enter a drug rehabilitation program.

Let me tell you, dealing with difficult people sometimes requires understanding their vulnerabilities. Back in 2008, I shared with *AARP The Magazine* a situation where I needed to get someone’s attention. I discovered he’d broken the terms of his probation – specifically, he’d used an illegal substance. This wasn’t just a personal issue, it was a legal one, and that gave me the opening I needed. I brought this information to the court and the sheriff – it was the only way I could get through to him and ultimately, the only way I could resolve the situation.

Sheen described the experience as feeling like the ultimate betrayal, sharing this in a September 2025 interview on *Good Morning America*. He was promoting his very honest Netflix documentary, *aka Charlie Sheen*, and his memoir, *The Book of Sheen*, at the time.

He later realized it was love, the *Major League* actor explained. But at the time, it felt urgent, like a scene from his book where his bodyguard warns him that US Marshals are arriving and they have to leave immediately.

Charlie Sheen married Denise Richards on June 15, 2002. They had two daughters: Sami Sheen, born March 4, 2004, and Lola Sheen, born June 1, 2005. Denise Richards filed for divorce three months before Lola was born.

They briefly reconciled, but by early 2006 the split was back on.

When Richards requested a temporary restraining order in April, she claimed that Sheen had physically assaulted and threatened her life.

Charlie Sheen claimed the accusations weren’t true, but a judge temporarily ordered him to stay at least 300 feet away from the mother of his children and their daughters, only allowing visits with supervision.

Charlie Sheen called the accusations against him “vile, unconscionable, and baseless,” describing them as a clear attempt to damage his reputation. He stated that the claims made by Richards are completely without foundation, according to ABC News.

Looking back, navigating divorce is *never* easy, and it was certainly a journey for May and her ex. While they’ve reached a really good place now, co-parenting amicably, it took a while to get there. They finalized things about six months after signing a custody agreement, but honestly, there were years of court appearances and, unfortunately, some very public disagreements – I remember Charlie’s Twitter being quite a topic back then! It’s a testament to both of their willingness to eventually prioritize their family, though.

Charlie Sheen married real estate investor Brooke Mueller on May 30, 2008, and they had twin sons, Bob and Max, in March 2009.

On Christmas Day in 2009, Charlie Sheen was arrested in Aspen, Colorado, following accusations of domestic violence. His wife reported to police that he had threatened her with a knife, telling her she should be afraid.

After the incident, both Sheen and his wife entered rehabilitation facilities. Sheen admitted guilt to a lesser charge of misdemeanor assault in August 2010 and was permitted to continue treatment rather than face jail time.

He stated he will follow the court’s ruling and is eager to move forward with his life and resolve this matter.

In October 2010, Charlie Sheen was hospitalized after experiencing a negative reaction to medication. Police were called to the Plaza Hotel in New York City because of reports of someone experiencing an emotional disturbance. His wife, Brooke Richards, and their daughters were staying in a different room at the hotel, and actress Capri Anderson was with Sheen at the time.

Both he and Mueller filed for divorce on November 1st. He stated their separation began on the day they had a disagreement in Aspen. The divorce was completed in 2011.

The 2011 public feud between Charlie Sheen and Chuck Lorre, the creator of *Two and a Half Men*, was incredibly strange. Ultimately, after seven seasons, Sheen-a four-time Emmy nominee-was fired from the popular CBS show.

Charlie Sheen reached a settlement with Warner Bros. in September, resolving his $100 million lawsuit over his firing. Reports indicate the final settlement amount was $25 million.

Looking back at the chaotic period when he famously talked about having “tiger blood” and dating “goddesses,” Sheen realized ten years later that he hadn’t actually been successful, despite what he’d claimed at the time.

He recalled people telling him how much they enjoyed watching it, saying they found it ‘so cool’ and ‘fun.’ They also expressed appreciation for his involvement and the energy surrounding the project, even claiming they had ‘stuck it to the man.’ However, he later reflected that all the excitement felt like a trade-off: he’d given up early retirement for what amounted to a fleeting online trend.

In November 2015, Charlie Sheen revealed on *Today* that he had been diagnosed with HIV about four years prior.

He remembers being deeply upset by everything that was happening in his life. He turned to drugs and alcohol, and he acknowledges he made some terrible choices during that time, taking full responsibility for his actions.

Sheen stated he’d paid individuals to keep quiet so much that it significantly harmed his financial future.

So, in confirming his status, he hoped to “release myself from this prison.”

In April 2025, Sami revealed that despite moving in with her father in 2021, she hadn’t spoken to Sheen in a year and hadn’t exchanged texts with him for half a year.

She explained on the *Casual Chaos* podcast with Gia Giudice that he began sending her strange and unwanted messages. She ultimately blocked him and told him to never contact her again, saying his behavior was unacceptable.

In a September 2025 interview on *Good Morning America*, Charlie Sheen expressed hope for a possible reconciliation, stating, “There’s always a chance for a better future.” However, he also admitted he was confused about what he would even apologize for, saying, “I honestly don’t know what I did wrong.”

The actor believes this is just a temporary issue, and he and his partner will resolve it. They’ve successfully overcome challenges in the past, and they don’t want to let a single disagreement ruin their strong relationship.

2025-09-23 22:54

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