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... more
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. more
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... more
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... more
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"). more
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... more
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.... more
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... more
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... more
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. more
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. more
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... more
Jake tells Charlie and Alan that he often overhears Judith and her fianc?, Herb (recurring guest star RYAN STILES), having sex, and he formulates a theory as to why his mom constantly gives Herb directions... more
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... more
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... more
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... more
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... more
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... more
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... more
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... more
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. more
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... more
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. more
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... more