Charlie volunteers to take care of Jake for the weekend.

When Jake's school principal demands to meet immediately with Alan concerning a picture Jake drew of a large-breasted schoolmate, Alan leaves a message asking Charlie to help.

Charlie is dismayed to learn that Alan's recent dating spree has been with Alan's ex-wife, Judith. Charlie fears he will rarely get to see Jake if Alan and Judith reconcile.

Alan infuriates Charlie when he gives Berta permission to move into the beach house for a couple of days. Charlie reprimands Alan and informs him that he's just a houseguest.

After a woman Charlie has been having sex with professes her love for him, he responds inappropriately and suffers from impotence.

Charlie is thrilled that he's dating Isabella, a wild, sexually uninhibited woman--until Alan points out that she's a spooky Satan worshiper.

Charlie finds himself in a compromising position after getting drunk and spending the evening with his stalker, Rose, celebrating her birthday.

After Charlie's romantic overtures towards Mia, an attractive ballet teacher, are rejected, Charlie tries to prove to Alan that he can persuade Mia to go on a date with him.

A wealthy, elderly woman named Norma (Cloris Leachman) is romantically interested in Alan.

Alan organises a family dinner to celebrate the publication of a newspaper article that describes him as a 'good doctor, good neighbour and a good guy', but Evelyn isn't impressed.

When Alan dates a cooking instructor, Sandy, both he and Charlie gain weight. Charlie refuses to allow Alan to break up with her, fearing the loss of her fabulous meals.

Charlie and Alan take Jake to a friend's house and go out for some sibling bonding, but Alan convinces himself that Jake was too eager to spend the weekend away from him.

No one believes Charlie when he says that his relationship with Mia is getting serious.

After a month and a half of abstinence, Charlie is quite eager to consummate his relationship with Mia. Unfortunately, there are still a few roadblocks.

Charlie's lifestyle causes tension with Mia. Charlie can't keep pace with the healthy routine that Mia has introduced, so he sneaks cigars and beers in the garage.

Concerned that he is dating a woman half his age--and mortified to introduce her to Evelyn--Alan tries to avoid bringing his 22-year-old girlfriend, Kandi, to Jake's birthday party.

When he is nominated for an advertising award, Charlie boycotts the banquet, having lost several years in a row to his cocky competitor, Archie.

Alan gets into financial trouble because he keeps paying the expenses of his young girlfriend, Kandi. When Kandi's old car breaks down, Alan leases a new one for her.

Kandi moves in with Alan and Charlie, causing tension in the house. Charlie's not happy to learn of the new arrangement, considering he has been having a dry spell with women.

Charlie is now dating Kandi's mother, Mandi. Meanwhile, Alan is depressed because Kandi has left him and is staying with bitter Judith, who brainwashed her against him.

Jake's teacher, Francine, calls Alan and Judith into her classroom to discuss Jake's lack of interest in school.

When a cute girl from Jake's school invites Jake to a party, Charlie butts in on Alan's milestone moment with his son by offering his own words of wisdom on women.

When Charlie finds out that his ex, Mia, is in town with her dance troupe and wants him to come to her performance, he tries to behave as if he were no longer attracted to her.

With Charlie and Mia arranging their wedding, their families meet, and things immediately begin to fall apart. Rose takes Charlie's engagement news hard.