[2] 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.

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.

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).

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.

Meanwhile, the extreme financial hardship at Chez Harper leads Alan to become a guinea pig for medical products, making some nasty side-effects.

Linda's ex-husband hears some of the songs he recorded for Brandon and Charlie is given the job of making children's jingles.

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

Charlie and Alan are introduced to Teddy's daughter, Courtney (Jenny McCarthy), who works as a sales representative for luxury cars.

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.

Note: For this episode, Jon Cryer was nominated for the 2008 Primetime Emmy Award for Outstanding Supporting Actor in a Comedy Series.

Alan begins dating a divorced woman (Christina Moore) who used to best-couple friends with him and Judith.

Evelyn's husband, Teddy, is found dead, in this spoof episode of CSI: Crime Scene Investigation.

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.

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.