Late last year, on the set of their hit CBS sitcom Two and a Half Men, Jon Cryer had some bad news for his costar Charlie Sheen: Cryer and his wife of four years, Sarah Trigger, were separating. No sooner had he spilled the beans than Cryer wished he hadn't. "The thing is, you can't complain about something with Charlie because he will always try to fix it," says Cryer. "He said, 'Hey man, you know, if you need a place to stay, you can crash with Denise and me,' " referring to actress wife Denise Richards. Cryer was incredulous. "Dude," he said, "how much like the show do you want your life to be?"

Good question. On Men, Cryer plays Alan Harper, a newly divorced father of an 11-year-old son who moves in with his single, swinging brother Charlie (played by Sheen). "Look at me," Cryer said in a recent episode. "I'm a broke, hopelessly neurotic, middle-aged man who doesn't even know who he is or where he belongs. I have no wife, no home, nothing."

Life has not been nearly as bleak for Cryer, 39, who shares custody of their 4-year-old son Charlie with Trigger, 36, a British-born actress. "Thankfully my ex and I have managed a much more civil relationship than my character and his ex have," he says. And yet, "even when people try to be as civil as they possibly can, it hurts, it really hurts," says Cryer. "That hole you feel when you are not with your child is indescribable. There was an episode last year where Jake, my character's son, says, 'It's okay, Dad, don't worry about me.' When we shot that, I was practically bawling. Your kids really try to do that for you: They see you are hurting and they try to fix it. As a father, I'll tell you, that is brutal."

Sheen, for his part, says his offer to take Cryer in during those early dark days was spontaneous.
"I was just like, 'Dude, if it's too difficult at home and you need a place to get away...' " he says. "I was concerned with him as Jon. I wasn't even thinking of the comedic aspect of, 'Good God. This is life imitating art.' I didn't care about that."

Cryer, however, can't help seeing a connection. "As much as I don't want to be like Alan, in truth I really am," he says. "I am this repressed, kind of uptight, perpetually nervous guy."

Screenwriter Richard Schenkman, Cryer's best friend, disagrees. "Jon is in no way as uptight as that guy. He is much more fun than Alan and a lot cooler." Still, Cryer has always had a penchant for playing geeks—none more indelibly than lovelorn Duckie in 1986's Pretty in Pink (see box). Three years later he won acclaim as a mailroom clerk turned agent in the highly touted yet short-lived sitcom The Famous Teddy Z. After nerdy turns in at least three more failed series, "all of a sudden I wasn't even getting the jobs," he says. "In almost two and a half years I worked three weeks total. My agent said simply, 'You're cold. [Producers] don't want to take a chance on you now.'"

It came at the worst possible time for Cryer, who had just married Trigger, his girlfriend of five years (they met during production of his 1998 sitcom Getting Personal). "I had bought a nice house, and my son had been born," he says. Determined to score another sitcom, in 2002 he fired his manager of 20 years and "started auditioning for everything," he says, including Two and a Half Men. "The network didn't want me. They wanted a new face." But Sheen (who had worked with Cryer in the 1991 spoof Hot Shots!) was sold on him from their first reading together. "I couldn't even put another face, another voice on Alan Harper," he says.

Seeing the show take off after its debut last September "filled me with elation. At the same time, my marriage was collapsing," says Cryer, who won't discuss the reasons. And so the eerie parallels with Alan began. "Last season, the day they reran the episode where my character gave a deposition in his divorce, I was giving my deposition in my real divorce," he says.

Now, seven months after he filed for divorce, Cryer is adjusting to life as a single guy. To furnish his new small Spanish-style rental in North Hollywood, he recently went shopping at IKEA. "I thought, 'Shelves and a desk: How hard can it be?' It turned into a bloody, glueful, sticky mess that resulted in some rickety furniture." His social life is also a bit shaky. "There are so many things that are just awful about dating," he says. "Besides the anxiety you feel about whether this person's going to like me, as a single parent, you also feel this weird guilt. You feel bad enjoying yourself when you're not around your child, but you can't include your child in your dating life because you don't want to confuse them."

But then Cryer confesses he can be a bit overprotective when it comes to his son. "There's a part of your mind that's always with your child—that says, 'I wonder if he is putting his finger in a socket,' " he says. "I am hoping that he grows up to be less fearful than me." And that he chooses another line of work. "Charlie's got charisma. He's the kind of kid people gather around," says his dad. "My ex and I would rather he not become an actor, but he certainly has a gleam in his eye."

Mike Lipton. Oliver Jones in Los Angeles

  • Contributors:
  • Oliver Jones.