Celebs Make Shocking Confessions About Their Lives

After his split from Sarah Trigger, Jon Cryer admitted he felt completely undateable. Emotionally wrecked and insecure, he wrote that he didn’t believe he had anything to offer a real relationship. At the suggestion of Charlie Sheen, he decided to pay for companionship just to regain confidence around women.

Cryer described those experiences as awkward and uncomfortable, including one brief connection that ended abruptly when he learned Sheen had previously slept with the same woman. After hearing why she and Sheen didn’t work out, Cryer immediately ended it. The confession is painfully honest, blending vulnerability, loneliness, and the strange realities of leaning on famous friends during a low point.