While spending time with Jake, Charlie finds it hard to enforce rules that Alan has set out for him. It gets to the point were Jake lures a flock of sea gulls into his room, and Charlie gets very upset. This prompts Jake to try and get Charlie to forgive him. Alan starts doing chores for Judith, in the hopes of them getting back together. During one of the tasks, Judith kisses Alan, leading him to believe that things will get back to the way they once were.
After spending a day at Disneyland, Jake gets sick and wants to go to his mothers' house, to have her take care of him. This sends Alan into a state of misery, as he realizes he's losing his wife, and son. Charlie suggests that they go drinking, and Alan agrees. After drinking the boys take a cab home, but at one point they end up at their mothers, where they try to tell her what they think of her, but fail in getting the point across.
Charlie is very unhappy with his housekeepers' decision to quit, after she experiences Alan's demanding ways. Alan then offers to take on the role of housekeeper, but this situation doesn't work at all. So Alan decides to get the housekeeper to come back. Before Alan leaves, he puts Charlie in charge of getting Jake ready for a dinner with his mother and grandparents. Charlie also tries to get Rose to move on, and date other men. He finds both situations to be bigger challenges then he first thought.
After spending a night in Las Vegas, Charlie decides to live up to his promise that he made to Jake about attending his soccer game. During the game, Charlie sets up a play-date with an unattached mother named Kate, and they hit it off. During one of their dates, Charlie seems like he's ready for a serious relation. Alan sets up a meeting with Gloria (one of the soccer moms) to write a soccer newsletter, but Gloria has other intentions for the evening, and he has no idea. During the evening another soccer mom, Brooke, tries to move in on Gloria's plans.
Charlie tries to teach Jake to avoid certain calls that Charlie doesn't want to deal with, like his mother (Evelyn) for one. Evelyn gets so frustrated with not being able to talk to Charlie, that she decides to drop in while in the neighborhood. She invites them to dinner, to meet her new boyfriend (Tommy). When the brothers get over to their mothers house, Charlie is shocked to realize that Tommy's daughter is Olivia, one of the people he has been avoiding. Olivia tries to confront Charlie about their situation, but doesn't get the answer she wants, and throws a drink in his face, then storms off. After a week of not being able to contact their mother, Alan gets worried about her. So the brothers decide to go to her house and see if she's okay. They find her sitting in the dark and drinking, and she informs them that Tommy dumped her for a younger women. Later the brothers get Jake to try and cheer her up.
After meeting Wendy, a one-night stand of Charlies, Jake befriends her. Charlie doesn't like this situation, as he believes Wendy is using Jake to further their relationship, and he has no intention to keep it going. It gets to the point were Wendy even starts spending time with Evelyn, and Charlie becomes desperate to get rid of Wendy. After Charlie breaks it off Jake becomes very unhappy with him, because he won't be able to see Wendy anymore. This forces Charlie to confront Jake and explain the situation as best as he can. Rose sees that Alan knows how to play scrabble, and asks him to teach her to play, he agrees. During the scrabble games the two bond, and Charlie suspects that she is using Alan to get closer to him, but doesn't pursue the issue.
While at the movies, the brothers bump into Judith and her new boyfriend. Seeing that Judith has changed her look, and the fact that Jake doesn't think Alan is as cool as Judith; prompts Alan to realize that if he wants to get back into the dating scene, he's going to have to change his look as well.