Jake is getting ready to start a new school as he advances to junior high, but his dad and uncle's scary stories might end his academic career a bit early. Alan and Charlie take him school shopping and find themselves in trouble, both there and later. Meanwhile, Charlie has a rash in a most inopportune area.

Charlie ends up having to go to one of Evelyn's firm get togethers, but the event ends up giving the two a friendship. However, Charlie sleeps with Margaret (Jennifer O'Dell), a woman that he met at the party against Evelyn's orders, but she firmly takes this into an advantage. Alan sleeps with a woman (Janeane Garofalo) who behaves oddly the next morning.

Note: For this episode, Holland Taylor was nominated for the 2008 Primetime Emmy Award for Outstanding Supporting Actress in a Comedy Series.

Alan convinces Charlie that he needs to date more respectable women and sets him up with a judge called Linda (Ming-Na Wen). The two double date and things do not go too well, with Charlie inexperienced at dating woman his own age. Desperate for a second chance, Charlie goes to great lengths to speak to Linda again, which include allowing himself to be caught by the police and sent to court to see her.

Charlie and Linda get closer to consummating their relationship, but Charlie has trouble focusing when he begins to see Rose's face everywhere he turns (the dog walker, the bartender and the house keeper). He visits Dr. Freeman who says that he is only imagining Rose because he is afraid to grow up. Reflecting on that, Charlie ends up on the next flight to London to find out if Rose is still truly there. Charlie does indeed find her there, and they go out for a drink at the local pub. While there, she asks for commitment in a relationship, scaring Charlie back to California as he is already in one. After Charlie and Rose leave to go to the pub, we see wigs and costumes in her apartment, revealing that this was part of Rose's scheme.

Note: This was the 100th episode of the show, and all seven of its writers had contributed to writing this episode.

Charlie discovers that he is good with kids while babysitting Linda's four-year-old son Brandon. Meanwhile, the extreme financial hardship at Chez Harper leads Alan to become a guinea pig for medical products, making some nasty side-effects. While babysitting, Charlie comes up with great funny jingles to help Brandon do as he is told, recording a CD for him. Linda's ex-husband hears some of the songs he recorded for Brandon and Charlie is given the job of making children's jingles.

Charlie and Linda attend a function crowning Linda judge of the year, but Evelyn gives him a pill that she believes to be a sedative. It turns out to be a wrong pill and therefore he acts crazy at the function, embarrassing her in front of the crowd. Meanwhile, Jake sneaks out to attend a rock concert after Alan forbade him to, and finds an irate Alan back home waiting for him, along with Charlie, whom Linda left because of the events.

After Alan and Charlie have a fight about Alan's role in the house, Alan packs Jake up and moves in with his mother. Evelyn and Teddy do not want Alan and Jake in their house and they go to great lengths to reconcile the siblings.

Charlie writes children's songs and finds success as Charlie Waffles. The kids and their parents love him, even signing CDs of his jingles. However, Charlie's newfound fame irritates Alan, and Charlie has a high-proof answer to his sudden stage fright, getting drunk, which actually works out, finding a huge fame at the live audience.

Note: For this episode, Charlie Sheen was nominated for the 2008 Primetime Emmy Award for Outstanding Lead Actor in a Comedy Series.
Note: The man on the TV with the guitar and singing/speaking is Raffi, best known for his children's music.

Charlie and Alan are introduced to Teddy's daughter, Courtney (Jenny McCarthy), who works as a sales representative for luxury cars. Teddy warns Charlie to stay away from her. Charlie, thinking Teddy is simply being a protective father, starts an affair with her instead, and when he is caught upstairs with her while Evelyn and Teddy are downstairs, she blackmails him into buying a new Ferrari from her. When all is revealed, Teddy tells Charlie that was why he was warning him.

First appearance of: Courtney Leopold
Title quotation from: Courtney, after Charlie explains that the Ferrari she is trying to sell him does not have much room.

Learning Charlie stole away a girl he liked in high school and getting angry about it, Alan gets revenge by stealing Charlie's french girlfriend Gabrielle (Justine Eyre). However, things don't really work out like he planned due to Gabrielle's behavior in bed. But Alan finds out that Charlie wanted to break up with Gabrielle by letting Alan steal her, and, at the same time, sees that Charlie is going out with Alan's high school crush again, causing Alan to be angrier than before. Elsewhere, Jake gets dumped by his girlfriend and he seeks advice from Charlie to patch things up.

Note: This was the last episode aired, prior to the 2007–2008 Writers' Strike.

Alan is unhappy about his sex-life with his new girlfriend, Donna (Kimberly Quinn), but is reluctant to break up with her. So he goes to Charlie for advice on breaking up with women. When he does end up breaking up with her, he is shocked to learn that she planned to have a threesome with her hot friend (Sandra Dee Robinson), sending Alan into tears. Meanwhile, Charlie helps a now-free Jake hit on a girl while the two are out to eat. But it ends badly for Charlie when he gets pepper sprayed in the face.

Note: This was the first episode aired since November 2007, due to the 2007–2008 Writers' Strike.
Note: For this episode, Jon Cryer was nominated for the 2008 Primetime Emmy Award for Outstanding Supporting Actor in a Comedy Series.

Charlie sleeps with a woman who is sick, and Charlie accidentally catches her flu. After nobody in his family is there to help him, Rose (who has returned from England) offers her help, but then hits it wild, making Charlie a prisoner in his own house. Meanwhile, Alan feels Jake is pulling away from him, which makes him feel sad.

Alan begins dating a divorced woman (Christina Moore) who used to best-couple friends with him and Judith. He's happy until he learns more about Herb and Judith's sex life than he actually wanted to know; eventually she breaks up with him and dumps him on the streets after he starts to question her too much about their sex life.

While at the coffee shop Charlie is recognised by a woman he dated, but Charlie cannot remember her name, which becomes a problem for him. Jake falls for the same woman's daughter. Charlie double-dates with Jake and fixes Alan up with a hooker, who can't tolerate him, while Charlie's attempt to hide the truth becomes very difficult.

After seeing Charlie with many females in the space of one day, Alan feels Charlie is unable to control his womanizing ways. Charlie goes to see Dr. Freeman, who makes him realize he is over-dating girls and having sex with them because, the whole time, he is missing the one girl who got away (Mia).

Evelyn and Teddy's wedding is under-way, and Alan helps the two make plans for the ceremony. Courtney tells Charlie that they cannot see each other anymore since they are going to be step-brother and sister, but Charlie can't accept it at all costs, and goes to desperate measures to change her mind, with the help of Rose.

Evelyn's husband, Teddy, is found dead, in this spoof episode of CSI: Crime Scene Investigation. The CSIs investigate the death at Charlie's house. During the interviewing process, it is revealed that Teddy and Courtney are con artists who were trying to steal huge money from both Charlie and Evelyn, causing Courtney to be arrested. (Note: George Eads from CSI guest-stars as one of the guests in Charlie's house with a brief role)

This was part of a writer exchange crossover with CSI: Crime Scene Investigation, with Chuck Lorre & Lee Aronsohn writing the CSI episode "Two and a Half Deaths" that also includes cameos from Charlie Sheen, Jon Cryer and Angus T. Jones.

Last appearance of: Teddy Leopold
Note: This episode was selected as a Primetime Emmy Award submission for Conchata Ferrell for Outstanding Supporting Actress in a Comedy Series, but ended up not receiving a nomination.
Note: When released on DVD, the recap seen in the original broadcast was not included.

Alan tries to get Jake to complete a book report about The Taming of the Shrew, but Jake keeps losing the book and neglects to do the report. Meanwhile, when they arrive at the library, Charlie seeks relationship advice in the books and finds himself attracted to an older self-help author (Susan Blakely), whom he meets at a book store. Alan is also obsessed with her, thinking of her as a second mother.

Charlie's relationship with Angie becomes jeopardized after he meets her son's fiancé (Virginia Williams), realizing it's not for the first time; she is one of his ex-girlfriends. Things get worse when she tries to hook up with Charlie again, and she leaves her future husband when Charlie rejects her, causing him to break his relationship with Angie. Meanwhile, Alan tries to get Jake to study for his Algebra exam, but Jake has other ideas in mind.