The Emmy-winning fourth season of television's top comedy starts with a shock (Alan's getting divorced?again) and ends with a rock (the diamond that Evelyn's (Holland Taylor) new boyfriend wants to put on her finger.
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.
Alan feels guilty when Charlie finally tells him why he broke up with Mia. The truth is that Charlie and Mia didn't get married because she had wanted Alan and Jake to move out.
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.
Alan and Kandi become embroiled in an unconventional custody battle. Alan is determined to retain custody of his and Kandi's dog after Kandi walks away from their split with both the condominium and the car.
Alan is overjoyed that he'll no longer owe Judith alimony when she marries her new fiance, Herb (recurring guest star RYAN STILES - "The Drew Carey Show").
Although Charlie doesn't get along with his sharp-tongued, passive- aggressive mother, he is strangely attracted to Lydia (recurring guest star KATHERINE LaNASA - "Justice"), a blonde high-end real estate agent--which is exactly what his mother is.
When Berta swears vengeance on the married man who got her daughter, Naomi (recurring guest star SARA RUE), pregnant, she forces Charlie to come with her. Meanwhile, Naomi helps Berta with the housework. And Alan reveals an unusual fetish.
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.
During a double date, Charlie becomes annoyed with Alan for constantly borrowing money and promising to pay the tab "next time." When Alan leaves Charlie with the check after dinner, Charlie tries to beat him at his own game.
Charlie must choose between his girlfriend Lydia (recurring guest star KATHERINE LaNASA) and Berta as they fight for his allegiance, each thinking the other has crossed the line.
As Charlie prepares for a steamy Christmas Eve alone with his date, his friends and family keep dropping in--and staying--until Charlie finds himself hosting an unplanned, unwanted holiday party.
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.
Jake tells Charlie and Alan that he often overhears Judith and her fiance, Herb (recurring guest star RYAN STILES), having sex, and he formulates a theory as to why his mom constantly gives Herb directions in bed.
After getting to know Danielle (BROOKE SHIELDS - "Nip/Tuck," "Suddenly Susan"), the guys' hot new neighbor, Charlie discovers that she shares some common interests with Alan and proceeds--with ulterior motives--to set them up.
When Rose announces that she is moving to London permanently, Charlie doesn't listen at first. But he eventually realizes that he must face his true feelings for her. Meanwhile, Alan tries online dating--with unforeseen results.
A sexy young girl whom Charlie has been dating cajoles him into going to a hot new club and bringing Alan along to meet her friend. But when they arrive, Charlie and Alan are mortified to learn that the partygoers consider them old.
After Alan and Charlie tell Evelyn that none of her acquaintances will mourn her when she dies, she bitterly ignores them for a few weeks. The guys then discover that, instead of trying to be more pleasant to the people she knows, Evelyn has brought together a whole new group of "friends," including two men and a cute boy who seem suspiciously like adoring versions of Charlie, Alan and Jake.
When Jake starts covering his walls with posters of sexy women, Alan realizes that his son is almost grown up. He makes a last-minute attempt at father-son bonding, wanting to make the most of what little childhood Jake has left. Meanwhile, Kandi embarks on a new career as an actress.
As Judith and Herb's (recurring guest star RYAN STILES) wedding nears, Charlie gets close to Herb's witty sister, Myra (recurring guest star JUDY GREER - "Arrested Development"). But Charlie's flirtation does not please Judith, who orders Alan to make Charlie stop pursuing Myra.
While Alan prepares Jake for Judith's wedding, Charlie continues his fling with Herb's (recurring guest star RYAN STILES) sister, Myra (recurring guest star JUDY GREER). Besides Judith's disapproval of the relationship, Charlie gets a surprise from Myra after admitting that he truly likes her.
When Greg (MATT ROTH), a single father from Alan's support group who has been spending a lot of time with Alan, reveals that he is gay, Charlie suspects that Greg is attracted to Alan.
Jake experiences a windfall when Charlie takes him to the racetrack. Meanwhile, Alan is stuck in a hellish Department of Motor Vehicles office. Series star JON CRYER made his directorial debut with the episode. JOEL MURRAY ("Dharma & Greg") guest stars as Petey.
Charlie loses a woman he is dating to a young, handsome handyman, Fernando (Grammy Award-winning recording artist ENRIQUE IGLESIAS), who is working on Charlie's house.
Charlie and Alan must confront their "daddy issues" when Evelyn's new boyfriend, Teddy (ROBERT WAGNER - "Hart to Hart"), invites them to Las Vegas on his private jet. MIKE CONNORS ("Mannix") guest stars as Hugo.