Jake's sullen mood baffles and bothers the family and prompts Alan and Judith to take him to a child psychologist.

After Charlie takes Alan to an eye doctor, they end up at cafe where they bump into Charlie's ex-girlfriend, Sherri. While there Alan shows an interest in Sherri, and decides to ask her out. The problem is that Alan can't get over Sherri's relationship with Charlie.

Evelyn buys Alan a new Sports car causing Charlie to claim that his brother has sold his soul to the Devil. The next day, Evelyn extracts payment by insisting that Alan go on a blind, double date with her, her new beau and his daughter. At the restaurant, Alan learns that his mother and boyfriend will not be able to join them because there was a mixup between his heart medication and Viagra and she didn't want to ""waste it"". As a result, Alan is left to deal with the daughter, who is on a weekend pass from a rehab center and still has some loose screws. Alan eventually gets her back to the beach house only to have her drive off in his new sports car and become the object of a televised high-speed car chase.

After falling off the roof, Alan needs Charlie's help in looking after Jake, which interferes with Charlie's social life.

Jake gets suspended from school after drawing an offensive picture of a girl in his class that has large breasts. Meanwhile, Charlie is asked to watch over Alan's chiropractic office after pulling an all-nighter.

Alan has been dating a lot, and Charlie soon finds out that it has been one woman - his ex-wife, Judith. He tries to stop Alan, and even brings Rose, Evelyn and Berta to interfere - but Alan ignores them all.

Berta causes tension between Charlie and Alan, when she temporarily moves in with them

Charlie learns he can't be in a long-lasting relationship, becuase of unresolved issues he has with his mother. Jake asks Charlie for advice about a girl at school.

Ignoring Alan's warnings, Charlie continues to date Isabella until she threatens to put a curse on his manhood.

Charlie wakes up with Rose the morning after her birthday party. Her irate father comes to ask Charlie about what the future holds for him and Rose, but the unexpected happens when Evelyn shows up.

Charlie tricks Jake into taking ballet lessons, so he can get close to the teacher.

Charlie arranges a romantic date with Mia in the hopes of consummating their relationship. Alan begins to date Charlie's most recent ex-girlfriend.

Charlie has trouble keeping up with Mia's healthy lifestyle, so he begins to sneak beers, cigars, and burgers behind her back. When Mia finds out what he was doing, Charlie has to decide if he is truly in love with her or just whipped.

Alan has trouble deciding if he should bring his younger girlfriend to Jake's birthday party to meet his mom and his ex-wife. Rose tries to get her boyfriend to act more like Charlie.

Charlie is nominated for an advertising award, but he decides to boycott it because his arch nemesis always wins. The rest of his family tries to trick him into going. Rose is having relationship problems with Gordon and seeks help from Charlie.

Alan starts to have financial problems when he starts paying for his girlfriend's bills, so Charlie tries to get him to break up with her. Meanwhile, Judith is after Alan because he is late in paying his alimony check.

Charlie is surprised to find out that Kandi has been living with them for the last three weeks. Alan is having a tough time helping Kandi earn a living. Charlie has lost his sense because of the dry-spell he is going through.

Alan tries to win Kandi back. Meanwhile, Charlie starts to sleep with her mom, Mandi, and Judith gets set up with her father, Andy.

Charlie returns to his bachelor lifestyle after Alan moves out of the house. Alan suffers a breakdown after his divorce from Kandi.

Charlie finally tells Alan that he didn't marry Mia because she wanted Alan and Jake to move out of the house, but Alan finds a hole in his logic. Charlie and Alan deal with a noisy neighbor who constantly sings all the time, who happens to be Steven Tyler.

Charlie tries to surf to impress Dottie, a beautiful woman he just met, but after he nearly drowns he is convinced that he saw his late father.

Alan tries to hire his ex-wife's lawyer to help him win custody over the dog he and Kandi shared.

Alan is overjoyed by the prospect of Judith remarrying, as he would no longer have to pay alimony. Alan gets Charlie to help him when it looks like the marriage maybe derailed due to Jake’s dislike of his mother’s fiancé.

Charlie is dating a woman whose personality and life are like his mother’s.

Berta's daughter, Naomi is pregnant and Berta drags Charlie with her when she confronts the baby’s father. Alan reveals a secret fetish.

Alan suffers from insomnia. He visits his psychiatrist, who reveals that the cause of Alan's sleepless nights is his jealousy towards Charlie, and his inability to glide through life.

Charlie gets tired of Alan's mooching and reaches the breaking point during the brothers' double date. Jake is left home alone for the first time.

Worrying Charlie may get rid of one of them, Berta and Lydia fight over him. Meanwhile, Kandi does everything she can to stop Alan from selling their condo.

Charlie's friends and family put a crimp in his plan for a romantic Christmas Eve date. When Evelyn sees who the date is, she goes to great lengths to force a wedge between them.

Jake shares that he has heard his mother having sex with her fiancée, Herb; this revelation brings up a repressed memory for Charlie. This leads Charlie to seek help from Rose.

Charlie sets Alan up with their new neighbour. But he gets jealous when the two form a bond.

After Evelyn tells Alan and Charlie how she feels about there being no mourners at her friend’s funeral, the boys share their feelings that this could also be the case at her funeral. Evelyn tries to prove them wrong by introducing them to a couple she help adopt a boy from China. The boys return fire by inviting the young man to a play date with Jake.

Alan tries to bond with Jake when he realizes that his childhood is almost over. Kandi pursues a career in acting.

Charlie takes a liking to Myra, the witty sister of Judith's fiancé, Herb.