Charlie Sheen has always been a man of extremes: sitcom megastar, Hollywood bad boy, tabloid addict, and self-proclaimed “warlock with tiger blood.” But his latest revelation—casually dropped in his new memoir The Book of Sheen and the Netflix documentary aka Charlie Sheen—may be his most culturally resonant yet.
After decades of cultivating a hyper-hetero image, Sheen has confirmed what had long been whispered: yes, he has slept with men. He calls it “flipping the menu over.”
As with all things Sheen, the phrasing is outrageous, a little absurd, and, in its way, disarmingly honest. Sexuality, he seems to suggest, is a buffet.
But the revelation also opens a surprising question: what would it mean—for him, for Hollywood, for all of us—if Charlie Sheen began dating men publicly?
The Case for Sheen, the Gay Bachelor
Let’s be clear: Sheen insists he’s been celibate for nearly a decade and describes his romantic life today as “uneventful.” But culture doesn’t deal in uneventful Charlie Sheen. It deals in spectacle, redemption arcs, and improbable reinventions. A public relationship with another man would be all three.
Consider the symbolic power. Here is a man once caricatured as the ultimate Hollywood lothario—the sitcom star who burned through marriages, Playboy models, and drug binges with equal abandon—suddenly embodying a different kind of masculinity. Not the conqueror of women, but the partner of another man.
In a moment when conversations around fluidity and late-in-life honesty are gaining visibility, Sheen’s pivot could do something radical: normalize the idea that sexuality is not a fixed point, even for a man who once represented its most rigid stereotype.
Who Would Dare?
Speculation is inevitable. If Sheen were to rejoin the dating pool, who might be willing—or brave—enough to sit across from him at dinner?
Pop stars like Troye Sivan or Lil Nas X could inject him with cultural currency. Sivan’s sincerity and youth would make Sheen look almost paternal, while Nas’s flair for spectacle would turn every red carpet into performance art. A Lil Nas X–Charlie Sheen pairing might actually crash the internet, and isn’t that the highest form of relevance?
Comedians like Bowen Yang or Ryan O’Connell could offer balance. Yang’s wit could puncture Sheen’s bluster, while O’Connell’s frankness about identity could model the kind of vulnerability Sheen has long avoided. Imagine Sheen trying to rant about “winning” while Bowen calmly eviscerates him with a perfectly timed zinger.
Then there are the safer bets. Andy Cohen, the Bravo impresario, has survived Real Housewives table flips; he could certainly survive a Sheen outburst. Ross Mathews, the genial pop-culture commentator, might be the gentlest choice of all—able to soften Sheen’s image by simply standing next to him and smiling.
The Case Against
But let’s not confuse possibility with probability. The scars of Sheen’s past—his substance abuse, his public meltdowns, his treatment of women—remain raw. Many in the LGBTQ community might question whether elevating Sheen as some kind of queer icon is wise, or even fair. Do we really want the man who once called himself an “F-18” to become a spokesperson for fluidity?
More practically, Sheen himself may not want it. His description of celibacy as “uneventful” carried a note of relief, even peace. For a man whose life has been defined by chaos, uneventful may feel like winning.
Why This Moment Matters
Even if Sheen never dates again, his admission has cultural weight. He is not a Gen Z pop star or a queer influencer with a carefully calibrated coming-out story. He is Charlie Sheen—brash, damaged, complicated, and still, somehow, oddly compelling. By acknowledging his same-sex experiences, he widens the frame of who can be part of the conversation.
His revelation also challenges the idea that sexual exploration is confined to youth, or that past behavior must be erased in order to embrace present truth. Sheen is 59. If he can flip the menu in midlife, what does that say to others who have felt locked into identities that no longer fit?
The Conclusion
So, should Charlie Sheen date another man—and if so, which one? The gossip columnist in me would love to see him on Lil Nas X’s arm, dressed in matching leather at the Met Gala. The strategist in me thinks Andy Cohen could manage him into redemption. The romantic in me thinks Ross Mathews could coax out a softer side.
But the realist in me suspects none of this will happen. Sheen has lived enough lives for ten people. If celibacy gives him peace, that may be his greatest plot twist yet.
Still, the fact that we can even imagine Charlie Sheen in a same-sex relationship—and take it seriously—tells us something. It tells us that cultural perceptions shift, sometimes in the most unexpected places. And it tells us that even Hollywood’s most notorious straight man can help rewrite the script.
And if he ever does order off that flipped menu again? I, for one, will be watching the table very closely.
Rob Shuter is a celebrity journalist, talk-show host, and former publicist who has represented stars including Jennifer Lopez, Alicia Keys, Kate Spade, Diddy, Jon Bon Jovi, Tyra Banks, Naomi Campbell, Jessica Simpson, and HRH Princess Michael of Kent. He is the author of The 4 Word Answer, a bestselling self-help book blending Hollywood stories with personal breakthroughs. Rob hosts Naughty But Nice with Rob, a top 20 iTunes podcast, and was the only entertainment columnist at The Huffington Post. A veteran of PR and magazines, he also helmed OK! Magazine. Read his latest exclusives at robshuter.substack.com