In a Malibu beach house, two very different men and one growing boy create a surrogate family unit that promises to make each one of them a better man.
Commercial jingle writer Charlie Harper 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, arrives with his 10-year-old son, Jake.
Charlie's life turns upside down when his brother and nephew move in. At the supermarket, Charlie discovers he can use 10-year-old Jake to attract women.
Unsure how to properly discipline Jake, Charlie ignores him after the child 'forgets' to stop feeding the seagulls and leaves the door open, allowing the gaggle of birds to enter the house. Meanwhile, Alan gets a surprise from Judith when he goes to fix her sprinklers.
When Alan's attempt to provide Jake with a fun-filled weekend backfires, Charlie tries to console his brother by taking him to a local bar and getting Alan totally inebriated. As Alan and Charlie travel home, their cab driver offers them some unsolicited therapy.
When Charlie's longtime cleaning lady, Berta, quits her job, Charlie quickly realises he can't function without her and sends Alan to lure her back. Meanwhile, Alan places Charlie in charge of getting Jake ready for Judith, who is coming to take her son out for dinner.
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After a drunken night in Las Vegas, Charlie reluctantly attends one of Jake's soccer games and soon discovers the advantages of going to these matches. The players' mothers are quite attractive, and Charlie makes a date with a particularly sexy soccer mom.
Charlie rethinks the way he treats women when he, Alan and Jake are forced to cheer up a pitiful Evelyn after her boyfriend terminates their relationship. Meanwhile, Charlie teaches Jake some valuable lessons about screening calls from women, but the lesson backfires.
Charlie's friend Cindy frequently showers at his house after surfing. When Jake sees a butterfly tattoo on Cindy's partially nude behind and later draws a picture of it in class, Judith gets angry and talks to Alan and Charlie about letting her son see half naked women.
When Alan and Judith argue during a rehearsal of a play that Jake and his classmates are rehearsing, Charlie is forced to handle a roomful of fourth graders alone. The kids think Charlie is a loser until they realise he wrote the "Maple Loops" cereal jingle.
Charlie likes his new girlfriend, Wendy, but becomes concerned when Jake forms a friendship with her. When Wendy charms Evelyn as well, Charlie worries that Wendy is expecting more from the relationship and ends it. When Jake gets mad at him, Charlie learns a lesson.
When Charlie finds out that his favourite ex-girlfriend, Lisa, is getting married, he desperately tries to prove to her that he has become a better family man than her fiancé, despite his inability to commit to her. But Charlie can only carry on the charade for so long.
Charlie and Jake convince Alan to get a makeover when it appears Judith is moving forward since the breakup, sporting a new hairdo and new date. But when Charlie takes Alan shopping, the brothers clash over what image is right for him.
When Charlie's cleaning woman, Berta, brings her sexy and rebellious 16-year-old daughter, Prudence, to Charlie's house, Jake develops a childish infatuation with her ... and Charlie and Alan try to restrain their interest in the flirtatious minor as well.
Desperate to get a date, Charlie volunteers Alan to escort the woman's sister, turning the date into a foursome. Charlie tries to speed Alan's recuperation from a cold, but when Charlie gets ill and Alan discovers how attractive the sister is, their roles reverse.
When Charlie learns that his credit rating is ruined, and his debts are all overdue, he discovers that his accountant, Stan, is completely inept. At Alan's urging, Charlie tries to reduce his spending habits, but he has a difficult time giving up his luxuries.
Charlie and Alan find Frankie, a sexy but seemingly crazy woman, hitting a car with a baseball bat. Charlie brings Frankie back to his Malibu home but the two brothers, both competing for her attention, are taken aback by a secret that she's been hiding.
Frankie explains why she's in hiding with her 8-year-old daughter, Joanie. Both of the men are romantically interested in Frankie, and she reciprocates with one of the brothers. And Joanie likes Jake, who is completely disinterested in her.
Alan offends Charlie by choosing their crazy cousins as Jake's guardians. Later, as Charlie and Jake play basketball, Jake falls, hitting his head. Charlie rushes him to the emergency room and finds that his charm with women doesn't work with the admitting nurse.
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, wants to be Charlie's friend.
Judith's sinister-but-sexy sister, Liz, plans to attend Jake's 11th birthday party. Alan asks Charlie to behave. But when Liz arrives, she ignores Charlie and flirts with Alan instead. Liz proceeds to cause a commotion between her sister and her ex-brother-in-law.
Jake becomes a brooding musician when he continuously plays "Smoke on the Water" on his guitar with an ever-present grumpy attitude. Finally, Judith convinces Alan that Jake needs professional assistance, and they enlist the help of Dr. Linda Freeman.
Charlie and Laura, Alan's divorce attorney, begin a relationship. Laura doesn't care that he dates other women, but she does have one request: Charlie must be available for her whenever she wants him. Charlie loves the idea, until Laura takes advantage of the situation.
Alan succumbs to Judith's demand that they take Jake to therapy every week but he doesn't realise that he, too, is having issues ... with sleepwalking. Evelyn hints to Charlie that Alan used to sleepwalk as a child, leading Charlie to come up with a clever new solution.
When Jake imitates one of Charlie's sexist remarks in front of Judith's support group, the women decide that Charlie's home is an unfit environment for the child. Charlie must cajole the support group in order to win his nephew back.
One of Charlie's many women fears she's pregnant, and Charlie is relieved when the lady finds out she's not. When Alan realises that this is not Charlie's first pregnancy scare, he suggests a permanent solution for Charlie ... a vasectomy.