Welcome back to the Harpers' Malibu beach house - home to one of the funniest TV comedy hits in a long, long time. Resolute bachelor Charlie's trying (but not very hard) to remember the name of the girl currently taking a shower upstairs.
Charlie Harper (series star CHARLIE SHEEN) is a well-to-do bachelor with a house at the beach, a Jaguar in the garage and an easy way with women. His casual Malibu lifestyle was interrupted when his tightly wound brother, Alan (series star JON CRYER), and Alan's young son, Jake (series star ANGUS T. JONES), came to stay with him.
At Charlie's urging, Alan decides to put his past behind him and returns a ceramic giraffe he vindictively took from Judith during the divorce. However, Judith does not remember the keepsake, and more importantly she has an attentive new boyfriend, Dr. Melnick (RYAN STILES - "The Drew Carey Show," "Whose Line Is It Anyway?"), who is Jake's pediatrician.
Jake thinks he's dreaming late one night when he sees the teacher who tried to get him suspended, Miss Pasternak (MISSI PYLE - "Bringing Down the House"), practically naked in Charlie's kitchen. When Jake refuses to go to school the next day, Charlie agrees to end the relationship with Miss Pasternak. Unfortunately, she gets upset, and Charlie and Jake both suffer.
Jake adores Judith's rich, new boyfriend because the man has a boat and a pool, and he promises to teach Jake how to snorkel and scuba dive. Feeling inadequate, Alan teaches his 11-year-old son how to drive a car. But when Judith's boyfriend ends the relationship, Jake becomes furious at his mother. Now it's Judith's turn to feel inadequate, and Alan does something he may regret.
Charlie dates a woman, Sherri (JERI RYAN - "Boston Public," "Star Trek: Voyager"), who is a self-centered, manipulative narcissist--a female Charlie. But Charlie doesn't like the way Sherri treats him. Meanwhile, Alan tries to instill some discipline in Jake to improve his son's homework habits.
When Evelyn tells Jake that Alan shoplifted a toy as a child, Alan denies the charge, as he has ever since the incident took place. He finally admits to Charlie his theory that maybe there is a "Bad Alan"--an evil side of him that stole the toy--which the good side of him works daily to suppress.
In order to serve as a good example to Jake, who has been disrespectful lately to his mother, Charlie and Alan begrudgingly agree to give their own mother a party to celebrate her real estate achievements. Berta suggests they hire her sister, Daisy (CAMRYN MANHEIM - "The Practice"), who owns a catering company.
Alan's expectations for a first date with Nancy (KELLEY WEST), a woman he met while shopping for groceries, are far exceeded when she introduces him to a world of sex he never knew existed.
Charlie encounters Lisa (recurring guest star DENISE RICHARDS, series star CHARLIE SHEEN's real-life wife), the woman he thought was "the one" until she informed him of her engagement another man.
Charlie writes the theme song for a new cartoon based on one of Jake's favorite comics, but Jake hates the song. Realizing that Jake knows the comic better than he does, Charlie enlists his nephew's help. Meanwhile, Rose invites Alan to a movie and surprises him with her intellect.
Charlie is surprised when a woman, Gail (JODI LYN O'KEEFE - "Nash Bridges"), with whom he flirts in a bar, rejects his overtures and tells him that women around town have been comparing notes on his philandering. Later, Jake mentions that he did an Internet search on Charlie's name and found something interesting.
Jamie (PAGET BREWSTER - "Huff," "Friends"), Alan's close high school friend, visits Alan at the house. Charlie used to make fun of Jamie when they were teenagers, but when the two brothers see how attractive she is now, they both vie for her affections. However, Jamie has a plan of her own.
When an earthquake causes plumbing damage in Judith's home, Alan allows her to move into the beach house temporarily--much to Charlie's displeasure. After a few days, Charlie and Jake can no longer bear Judith's presence, and though he pretends otherwise, Alan is jealous when Judith goes on a date with another man.
After Evelyn undermines Jake's confidence by belittling his hard-earned high grade on a test, Alan decides to cut her out of their lives. When Charlie and Alan receive news that Evelyn is in the hospital, they realize it's a ploy for her to get back into their lives.
On a boring, rainy weekend, Charlie convinces Alan to ride with Jake and him to Las Vegas. Apprehensive about his upcoming colonoscopy, Alan agrees that the diversion will be good for him. After Alan packs numerous suitcases, and the guys are ready to leave, Jake becomes physically ill.
Judith takes a vacation and leaves Jake with Alan. But then Alan finds out he's being audited by the Internal Revenue Service. Burdened with this last-minute misfortune, he's forced to leave Jake in Charlie's irresponsible hands and hopes that his brother can get Jake to school.
While in a precarious position with a woman, Charlie injures his back and won't let Alan--a chiropractor--help him. After Alan drives Charlie to the doctor's office, Charlie is surprised to learn that his physician died four years ago, and a beautiful female, Dr. Michelle Talmadge (ALICIA COPPOLA - "Bull"), has replaced him. Meanwhile, Berta teaches Jake a lesson.
Charlie masquerades as a homosexual so that Eric (DAVID STARZYK), the gay owner of an advertising agency, will continue to give Charlie more jingles to write. Charlie convinces Alan to pretend to be his gay partner and attend a party hosted by Eric.
While at a coffee shop, Alan and Charlie encounter Sherri (recurring guest star JERI RYAN - "Boston Public"), a woman who once dated Charlie just so she could have sex with him. Alan is enchanted with her beauty, so Charlie encourages Alan to ignore his memories of teenage rejection and ask her on a date.
Evelyn harasses Charlie for not calling her, and Judith bills Alan for an expensive pair of tennis shoes she bought Jake. Unable to express the anger they have towards the women in their lives, Charlie and Alan lash out at each other. Rose--with her questionable background in behavioral psychology--tries to help the two brothers sort out their feelings.
While scanning the obituaries for potential property listings, Evelyn discovers that her second husband, Harry, has died. Although pleased that Alan agrees to attend the funeral with her, she's furious to hear that he had stayed in contact with Harry over the years.
After Evelyn gives Alan a loan so he can purchase a new Porsche, Charlie informs his brother that Alan has sold his soul to the devil. Evelyn proves Charlie is right when she coerces Alan to go on a double date with Trudy (CHLOE WEBB - "China Beach," "Sid and Nancy")--whose father Evelyn wants as a boyfriend.
When Evelyn learns that Jake spent his entire spring vacation with his other grandparents, she pressures Alan into letting Jake stay with her for a night. Concerned that Evelyn will destroy Jake's life the way she destroyed theirs, Alan and Charlie grudgingly take a resentful Jake to Evelyn's home and quickly flee to Charlie's favorite bar.
Charlie has sex with a gorgeous young woman, Natalie (KAREN TRELLA), without realizing she's married to an elderly man, Norman (ORSON BEAN - "Dr. Quinn, Medicine Woman"). At school, Jake is required to give a report to his fifth-grade class about his weekend.