Two and a Half Men (season 5)

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.

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, Evelyn is one step ahead of Charlie when he becomes interested in one of her clients. A woman Alan sleeps with behaves oddly the next morning.

Alan convinces Charlie that he needs to date more respectable women and sets him up with a judge called Linda (Ming-Na). The two double date and things don't go too well. 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. Charlie ends up flying to London to find out if Rose is still truly there. Charlie does indeed find her there, but she ask for commitment in a relationship, scaring Charlie back to California as he is already in one.

Note: This was the 100th episode of the show, and all 7 of its writers are contributed to writing this episode.

Charlie discovers that he's 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. While babysitting, Charlie comes up with great funny jingles to help Brandon do as he's told. Linda's ex-husband hears some of the songs he recorded for Bradon and Charlie is given the job of making children's jingles.

Charlie and Linda attend a function crowning Linda judge of the year, but a pill Evelyn gives him beforehand ruins their relationship. Meanwhile, Jake sneaks out to attend a rock concert, and finds an irate Alan back home waiting for him.

After Alan and Charlie have a fight about Alan's role in the house, Alan packs Jake up and moves in with his mother. Mom and Teddy don't want Alan there and go to great lengths to reconcile the siblings.

Charlie writes a children's song and finds success as Charlie Waffles. The kids and their parents love him. However, Charlie's new found fame irritates Alan, and Charlie has a high-proof answer to his sudden stage fright.

Note: For this episode, Charlie Sheen was nominated for the 2008 Emmy for Outstanding Lead Actor in a Comedy Series.

After Charlie is introduced to Teddy's daughter, Courtney (Jenny McCarthy), Teddy warns him to stay away from her. Charlie, unaware of what Courtney is capable of, tries but fails, and becomes blackmailed into buying a new car. (When released on DVD, this episode was titled "Shoes, Hats, Pickle Jar Lids." The title is not quoted in the episode.)

First appearance of: Courtney Leopold

Alan learns Charlie stole away a girl he liked in high school. He decides to get revenge by stealing Charlie's French girlfriend Gabrielle (Justine Eyre), but things don't really work out like he planned; Jake gets dumped by his girlfriend and he seeks advice from Charlie.

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). This leads him wanting to break up with her - but he can't, and goes to Charlie for advice; Charlie helps Jake hit on a girl while the two are out to eat.

Note: This was the first episode aired since November 2007, due to the 2007-2008 Writers' Strike.

Charlie sleeps with a woman who is sick, and Charlie catches her flu. After nobody in his family is there to help him, Rose (who has returned from England) offers her help; Alan feels Jake is pulling away from him.

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 wanted to know.

While at the coffee shop Charlie is recognised by a woman he dated but Charlie cannot remember her name and 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.

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 his shrink (Jane Lynch), who makes him realize he's missing the one girl who got away - Mia.

Evelyn and Teddy's wedding is under-way, and Alan helps the two make plans. Courtney tells Charlie that they cannot see each other anymore, but Charlie can't accept that, and tries to change her mind.

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, a few secrets about Teddy are revealed.

Charlie seeks relationship advice and finds himself attracted to an older self-help author (Susan Blakely); Alan's insistence that Jake complete his The Taming of the Shrew book report is hampered by Jake's continually losing the book.

Charlie's relationship with Angie becomes jeopardized after he meets her son's fiancé (Virginia Williams), realizing it's not for the first time; Alan tries to get Jake to study for his Algebra exam, but Jake has other ideas.