Commercial jingle writer Charlie Harper (series star Charlie Sheen) is a wealthy bachelor with a house at the beach, a Jaguar in the garage and an easy way with women. But his Malibu lifestyle is interrupted when his uptight chiropractor brother, Alan (series star Jon Cryer), arrives unexpectedly with Alan's 10-year-old son, Jake (series star Angus T. Jones). Alan's wife, Judith (series star Marin Hinkle), suspecting that she may be gay, wants a divorce. Charlie reluctantly allows Alan and Jake to live with him temporarily, but as it becomes increasingly obvious that Judith is never going to relent, Charlie and Alan's self-obsessed, controlling unmarried mother, Evelyn (series star Holland Taylor), offers to let father and son live with her. However, by that time, Charlie has formed a close bond with the clever Jake, even learning a few things about poker from the boy. Charlie also finds out that pretending to be a single dad with a cute kid can be a great lure for women. Meanwhile, Charlie tries to evade Ros

Charlie Harper (series star CHARLIE SHEEN) is a well-to-do bachelor with a house at the beach, a Jaguar in the garage and an easy way with women. His casual Malibu lifestyle was interrupted when his tightly wound brother, Alan (series star JON CRYER), and Alan's young son, Jake (series star ANGUS T. JONES), came to stay with him. Complicating matters further are Charlie and Alan's narcissistic, emotionally toxic mother, Evelyn (series star HOLLAND TAYLOR--not appearing in this episode); Alan's deeply neurotic ex-wife, Judith (series star MARIN HINKLE); Charlie's domineering, unapologetically blue-collar housekeeper, Berta (series star CONCHATA FERRELL--not appearing in this episode); and Rose (series star MELANIE LYNSKEY), a brilliantly manipulative and vaguely crazy neighbor who had a brief fling with Charlie, remains obsessed with him and is determined to stay in his life by whatever means necessary. Despite the complexities of their lives and their own strained relationship, Charlie and Alan have one thing

Charlie encounters Lisa (recurring guest star Denise Richards, series star Charlie Sheen's real-life wife), the woman he thought was "the one" until she informed him of her engagement another man. He's thrilled to learn that her marriage did not work out, even though there's now a new wrinkle in their potential relationship--a baby (played by Sheen and Richards' daughter, Sam, in her first screen appearance).

Charlie agrees to meet with a former girlfriend who ended their relationship years earlier, leaving Charlie devastated. But Charlie's in for a huge surprise when he discovers that she is now a he, and he, Bill (Chris O'Donnell - "Batman & Robin"), wants to be Charlie's friend. Initially disturbed by the sex change revelation, Charlie relents and befriends Bill. But Charlie and Alan are horrified when Bill starts dating their mother, and Evelyn becomes sexually intimate with Charlie's ex-girlfriend!

One of Charlie's many women fears she's pregnant, and Charlie is relieved when the lady finds out she's not. When Alan realizes that this is not Charlie's first pregnancy scare, he suggests a permanent solution for Charlie--a vasectomy. Charlie's doctor recommends freezing some s***m in case Charlie changes his mind about having children, but things don't go quite as planned.

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