Alan plans Evelyn's wedding to Teddy (ROBERT WAGNER), while Charlie pursues his future stepsister and Teddy's devious daughter, Courtney (JENNY McCARTHY).
Alan worries that Charlie's womanizing is out of control. JANE LYNCH returns as Charlie's therapist, and EMMANUELLE VAUGIER returns as Charlie's former fiancée, Mia.
Charlie goes with Jake on a double date and sets Alan up with a prostitute. Recurring guest star MELANIE LYNSKEY appears as Rose.
Alan dates one of his ex-wife's friends who reveals a secret about Judith's sex life. Recurring guest star RYAN STILES appears as Judith's second husband.
Rose (recurring guest star MELANIE LYNSKEY), Charlie's lovable stalker, is back from England and takes strange care of a very sick Charlie.
Seeing Alan not fully passionate about his relationship, Charlie coaches Alan in the fine art of breaking up with a woman.
While trying to help Jake get over a breakup, Alan discovers that it was Charlie who stole his high school girlfriend. Alan seeks revenge on Charlie by following the same advice Charlie dispenses to Jake.
After Evelyn and Teddy become engaged, Charlie struggles to fight his attraction to Teddy's daughter, Courtney, Charlie's soon-to-be stepsister.
Charlie finds success as a children's singing star, making Alan miserable. Guest star RICHARD KIND ("Spin City") appears as Artie, an executive at Charlie's record label.
Charlie and Alan argue over Alan's place in the house, prompting Alan and Jake to move in with Evelyn. Recurring guest star ROBERT WAGNER appears as Teddy, Evelyn's boyfriend.
Charlie's girlfriend, Linda (recurring guest star MING WEN), is embarrassed to be seen in public with him. Meanwhile, despite Alan forbidding it, Jake sneaks out to a concert.
Charlie has to find creative ways to entertain the 4-year-old son of his girlfriend, Linda (recurring guest star MING WEN). Meanwhile, Alan becomes a human "guinea pig."
In the landmark 100th episode, Charlie gets closer to consummating his relationship with Linda, but he keeps seeing Rose's face everywhere he turns. Recurring guest star JANE LYNCH appears as Dr. Freeman.
Tired of dating vapid young women, Charlie allows Alan to introduce him to a sophisticated, intelligent municipal court judge, Linda.
Charlie reacts oddly after an evening with his mother. And Alan's date, Sharon (JANEANE GAROFALO - "The Larry Sanders Show," "The West Wing"), reacts oddly after having sex with Alan.
In the fifth season premiere, Charlie and Alan try to prepare Jake for his first day of junior high school -- but they might end up traumatizing him instead.
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