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Biggest Bombshells From Charlie Sheen's Memoir 'The Book of Sheen': Sexual Encounters With Men, His Romance With Denise Richards and More

charlie sheen memoir the book of sheen biggest bombshells
Source: MEGA

Charlie Sheen's debut memoir, 'The Book of Sheen,' hits bookshelves just a day ahead of the premiere of his two-part Netflix documentary, 'aka Charlie Sheen.'

Sept. 9 2025, Published 6:59 a.m. ET

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Charlie Sheen Had Sexual Encounters With Men

charlie sheen memoir the book of sheen biggest bombshells
Source: MEGA

Charlie Sheen revealed his HIV diagnosis in November 2015.

Charlie Sheen dropped shocking revelations in his debut memoir, The Book of Sheen.

Out on September 9, the book included the highs and lows the Two and a Half Men actor went through over the years. It also unveiled bombshells, including Sheen's sexual encounters with men.

"I flipped the menu over," he wrote in the book.

Sheen also spoke about the subject in his two-part Netflix documentary, aka Charlie Sheen, admitting it was "f------ liberating" to "just talk about this stuff."

"It's like a train didn't come through the side of the restaurant. A f------ piano didn't fall out of the sky. No one ran into the room and shot me," he said.

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How Charlie Sheen and Denise Richards Fell for Each Other

charlie sheen
Source: MEGA

Charlie Sheen and Denise Richards were married from 2002 to 2006.

Sheen also reflected on his past romance with ex-wife Denise Richards, including their meeting on the set of the 2001 romantic comedy Good Advice.

Although they kept it professional while working together, the actor admitted in the book, "The more time we spent together on set, the more challenging it became to hide our unchaste chemistry."

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First Date With Denise Richards

charlie sheen
Source: MEGA

Denise Richards filed for divorce from Charlie Sheen in March 2005.

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Sheen and Richards' romance further blossomed when they watched a baseball game between the San Francisco Giants and the Houston Astros on October 4, 2001, for their first date.

"I carefully explained to D that if we were at a restaurant unable to watch, the main thing on my mind would be the game. (The main thing I could say out loud.)," he reminisced. "She completely understood and loved the idea of joining me to celebrate my passion for baseball. We ate our Zone meals from plastic bowls and hung on every pitch when Bonds was at the plate."

The Red Dawn actor wrote, "As we were saying good night at the elevator, D grabbed my face and pulled me into a long passionate kiss. The Baseball Gods had sprinkled some magic on our night. I was no longer thinking about the game."

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Charlie Sheen Attended a Private Men's Addiction Group Hosted by Matthew Perry

charlie sheen
Source: MEGA

Matthew Perry died from 'acute effects of ketamine' on October 28, 2023.

In The Book of Sheen, the 60-year-old Platoon star looked back at the time he attended a private men's addiction group hosted by Matthew Perry, saying they "shared a deeper truth we saw in each other."

"We were both, as Bobby Dee Jay used to say, 'veterans of the unspeakable,'" he added.

According to Sheen, the Friends actor had the ability to "turn every frown upside down" and that he had "never met anyone who more masterfully used humor as a deflector-shield."

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Charlie Sheen's Nights Out With The Brat Pack

charlie sheen memoir the book of sheen biggest bombshells
Source: MEGA

Charlie Sheen recalled partying with the members of The Brat Pack in the past.

In an excerpt shared by a news outlet, Sheen also cast his mind back to his nights out with The Brat Pack, which had an "all-star lineup" consisting of Rob Lowe, Demi Moore, Judd Nelson and Andrew McCarthy.

"As a group, they couldn't have been nicer to me; it was the gauntlet of hysteria they incited that had me constantly seeking shelter," he wrote.

Detailing one of the parties they had, Sheen recalled, "As soon as we'd exit the limo, I'd be relegated by their screaming fans to the role of stray dog, bringing up the rear for their crowd-parting, bar-hopping rambles. The night always began at the Hard Rock Cafe, then sashayed its way across the landscape of the gotta-be-seen popular hot spots. I felt so small and left out as I watched the Emilio [Estevez]-steered throng, redefining what a copious and decadent bask in the limelight could look like."

He also mentioned Chris Penn, who "was a passenger as well on many of those nights," though it changed after his film Footloose was released.

"That one hit me the hardest — my best friend in life was suddenly one of them. I was torn between hoping he was ready for it and knowing deep down that he wasn't," Sheen continued.

The Young Guns star called himself the "invisible valet" who carried the bags "for a clob of celebrity that had the masses hypnotized."

Sheen added, "I wanted to be told just once by their babe-squad that I mattered too. Knowing it wouldn't happen until my celebrated film had a line around the block required a patience I hadn't developed yet. To be in the crush of LA's insane mid-eighties club scene with Rob Lowe and a bevy of gorgeous gals was like being shipwrecked with a fat guy — you're gonna starve."

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