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 new boyfriend wants to put on her finger. In between though, Charlie Harper’s hip Malibu beach house is the place for laughs, gorgeous girls, single parenthood, celebrity neighbors, family dynamics, more girls and more laughs!
In the season premiere, Charlie deals with the immediate aftermath of his canceled wedding--and Alan's impulsive new marriage to 22-year-old Kandi (series star APRIL BOWLBY).
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.
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 fiancé, 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, a blonde high-end real estate agent.
When Berta swears vengeance on the married man who got her daughter, Naomi, pregnant, she forces Charlie to come with her. Meanwhile, Naomi helps Berta with the housework.
Unable to sleep, Alan takes Charlie's suggestion and goes for a jog on the beach. Alan turns to a psychiatrist in the hope that discovering the source of his insomnia will help alleviate it.
Charlie becomes annoyed with Alan for constantly borrowing money and promising to pay. 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 unwanted holiday party.
When Berta discovers that Alan has been secretly dating her daughter, Naomi, 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 fiancé, Herb, having sex, and he formulates a theory as to why his mom constantly gives Herb directions in bed.
After getting to know Danielle, 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.
A sexy young girl whom Charlie has been dating cajoles him into going to a hot new club. 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.
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.
As Judith and Herb's wedding nears, Charlie gets close to Herb's witty sister, Myra. 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 sister, Myra. 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.
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, invites them to Las Vegas on his private jet. MIKE CONNORS ("Mannix") guest stars as Hugo.