Charlie attempts to surf in order to impress a beautiful girl--with disastrous results. Later, after nearly drowning, he tells Alan that when Charlie's life was hanging in the balance, the guys' deceased father appeared to him and made a request that Charlie is reluctant to fulfill.

Charlie Harper (series star Charlie Sheen) is a well-to-do bachelor with a house at the beach, a Mercedes in the garage and an easy way with women. But his casual Malibu lifestyle was interrupted when his tightly wound brother, Alan (series star Jon Cryer), and Alan's 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); Alan's deeply neurotic ex- wife, Judith (series star Marin Hinkle); Charlie's domineering, unapologetically blue-collar housekeeper, Berta (series star Conchata Ferrell); and Rose (recurring guest 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 in common: They both love Jake and want what's best

Unable to sleep, Alan takes Charlie's suggestion and goes for a jog on the beach. After his run takes a disastrous turn, Alan turns to a psychiatrist in the hope that discovering the source of his insomnia will help alleviate it. Meanwhile, Jake pleads with Charlie not to date the hot mother of a classmate whom Jake likes.

When Berta discovers that Alan has been secretly dating her daughter, Naomi (recurring guest star Sara Rue), Alan expects trouble. But Berta's reaction is surprising--and much worse--than Alan could have imagined.

Alan is overjoyed that he'll no longer owe Judith alimony when she marries her new fianc , Herb (recurring guest star Ryan Stiles - "The Drew Carey Show"). However, when Judith and Herb's marriage plans are threatened due to Jake's disdain for his soon-to-be stepfather, Alan enlists Charlie's help, and the guys bond with Herb in an effort to improve his relationship with Jake.

Alan makes himself at home in Judith's house

Alan, Charlie, and Evelyn are spectators for Jake's very first day on the job

Charlie accuses Alan of siphoning gasoline out of his car

Alan and Berta reminisce about their first jobs

Alan and Judith debate the function of the spare bedroom while Jake puts his two cents in