Alan finds out that Charlie is part of an exclusive men's group and begs his brother to be a part of it. The group contains Sean Penn, Elvis Costello, Harry Dean Stanton, and Bobby Cooper.

Alan gets upset when he finds out Judith is dating Jake's pediatrician. Charlie points out, however, if she does marry him that Alan's alimony payments will end.

Jake is on the verge of getting suspended from school when he gives his teacher Miss Pyle the finger. Charlie tries to save Jake from the suspension by dating her, but fails several times.

Jake loves his mother's new boyfriend, Dr. Melnick, and won't stop talking about him, which bugs Alan. Evelyn borrows Charlie's car to impress a Saudi prince, so she can sell him real estate. When Charlie gets his car back, his mother's bra is found in the backseat. After he finds out why it is there, he trades it in.

Charlie meets somebody who can play hard to get better than he does, which makes him want her even more.

Alan denies ever shoplifting a toy as a child and fears that he he might have a dark side to him. Charlie admits that he planted it so he wouldn't get in trouble from their mom.

Charlie and Alan hire Berta's sister to help set up and cater a party that their mother had talked them into throwing her.

Alan meets the girl of his dreams in Nancy, who fulfills all of his desires which forces Charlie to take care of Jake. Trouble stirs a few days later when Alan decides he wants to marry her.

Charlie leaves a date he can't stand and ends up at a coffee shop where he runs into his ex-girlfriend, Lisa. She has broken up with her husband and left with a child. He tries to convince her that he's okay with her having a child. Jake tries to reason with his father why he isn't doing too well in school.

Jake helps Charlie come up with the theme song for a children's television show which is based on one of Jake's favorite comic books. Alan finds out how smart and fun Rose is when he starts spending more time with her.

Charlie finds out about a website created by him that shows how evil he is to women. Charlie goes and tries to find out who made the site by apologizing to all of them. He finds it hard to track down the creator when all the women take the apology a lot better than he expects.

Alan gets jealous when an old classmate who grew up to be a beautiful woman seems more interested in dating Charlie then himself.

Judith's house (actually Alan's of course) gets damaged during an earthquake and needs a place to stay. Alan offers Charlie's house without his permission. Charlie agrees, although not happy at first. Alan gets jealous when she goes on a date and has Charlie find him one to show her he can date just like anyone else.

After insulting the way Alan raises Jake, Alan and Charlie throw Evelyn out of the house. After ignoring her numerous phone calls, she feigns an emergency at the hospital which Aland and Charlie believe at first, until they catch her bluff.

Alan gets worried about a minor medical procedure he is going to face, so Charlie decides to take him to Vegas to get his mind off it.

Alan and Charlie have to take care of Jake the whole week while Judith takes a vacation, which proves harder then they imagined.

Alan takes Charlie to the hospital where he hits on a doctor he didn't know he had past history with. Berta is fed up with the way Jake uses the bathroom so she makes him clean it until he learns.

Charlie is invited to a party hosted by a gay ad-executive named Eric and he takes Alan pretending they are life partners. While there, Charlie meets Eric's ex-wife Pamela, and tries to get with her without Eric knowing.

After Charlie takes Alan to the eye doctor they end up at a cafe where they both bump into Charlie's ex-girlfriend, Sherri. Alan deicdes to ask her out after showing interest, but he can't get over the relationship she had with Charlie.

When Charlie and Alan take their personal frustrations out on each other, Rose buts in the middle to try and help them out.

Evelyn reads that her second husband Harry had died. They all attend the funeral. Jake is excited to see a dead guy while Charlie is excited about the opportunity of a newly single widow, and Alan is glad he can pay his respects to Harry.

Evelyn buys Alan a new sports car if he goes on a double date with her, her new boyfriend and his daughter. Alan finds out that his mother and her boyfriend can't make it, leaving the two of them alone, when Alan finds out she has a few loose screws and she ends up stealing his new car, and ending up on a televised high-speed car chase.

After learning that Jake spent his whole Spring Break at his other grandparents, Evelyn pressures Alan to have Jack spend more time with her. Alan is worried she will screw him up, like she did to him and Charlie. He agrees, though, and drops him off at her house. Alan meets a sexy woman at Charlie's favorite bar, which easily gets his mind off his son's bad time.

Jake must read what he did over the weekend as an essay to the class. The weekend consists of Charlie unknowingly sleeping with an elderly man's trophy wife over the weekend.