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.
Charlie finally gets a chance for a double date with a hot neighbor, who is out for revenge on her cheating husband, and her sister who's a hot soap opera actress, and needs Alan to come along. The problem is that Alan gets sick from Jake, so Charlie takes them to a steam room to help Alan get rid of his flu symptoms. This backfires, as Charlie also gets sick, but he has no intentions of canceling the date.
Judith believes that Jake is having a hard time dealing with his parent's divorce, after he starts annoying everyone with his non-stop guitar playing. So she suggests that they send Jake to a therapist. Alan doesn't agree at first, but after thinking about it, he believes it might not be such a bad idea.
Jake is very impressed and can't stop talking about his mother's new boyfriend, Dr. Melnick, which annoys Alan. While Evelyn borrows Charlie's car to help her impress a Saudi prince, because she wants to sell him real estate. When Charlie gets his car back, he discovers his mother's bra in the backseat. When he finds out why it's there he decides to trade in his car.
Alan meets a woman named Nancy at a grocery store, who fulfills every single one of his desires, forcing Charlie to take care of Jake. After knowing Nancy for a few days Alan decides to ask her to marry him, prompting Charlie to try and talk him out of it, and he even gets help from the brothers' mother.
When Charlie leaves the house to avoid a date that he can't stand, he ends up at a coffee shop, where he meets his old girlfriend Lisa. He finds out that she broke up with her husband, and now has a child. Now he must try to convince Lisa that he's okay with her having a child. While Jake tries to justify to his father why he isn't doing so well in school.
After getting unusually turned down at a bar, Charlie learns that a website has been made dedicated to exposing his lifestyle. Charlie sets out to find who created the site, making amends to all those he stood up, but it's harder than it looks when all the women take the apology better than expected.
After an earthquake hits, Judith's house is damaged and she needs a place to stay. So Alan decides to invite her to stay with him and Charlie, without getting Charlie's permission. Charlie isn't happy with this, but accepts it. Alan becomes jealous when Judith goes on a date, and asks Charlie to find him a date, so that he can show Judith that he dates as well.
When Judith decides to take a vacation, the brothers have to take care of Jake during the week. Alan finds it challenging, and even forgets to pick up Jake from soccer practice. When Alan finds out that he has to go to the I.R.S. because they're auditing him, he forces Charlie to take care of Jake, and Charlie doesn't do any better then Alan.
After Charlie has back pain, Alan decides to take him to the Hospital. While there Charlie can't stop hitting on the doctor who is examining him. The only problem is that he has a history with her that he can't remember. Berta is feed up with Jake's inability to use the bathroom properly, so she decides to make him clean it until he learns.
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.
Mia comes back to town with her dance troupe and invites Charlie to her performance. At first, he decides not to go and tries to convince Alan that he no longer has feelings for her. He goes to the see the performance and Mia explains that she wants some of Charlie’s sperm. Charlie responds by asking Mia for something.
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.
Charlie borrowed money from Alan and on the day he is supposed to pay him back, Alan goes to ask Charlie for the money. He again finds Charlie in bed with a beautiful woman. After Charlie shoos him out and assures him he'll get the money for him later that day, the woman asks if Charlie is really out of cash and Charlie tells her not to worry, that he has plenty of hooker money.