Evelyn offers to pay for Jake's college education, leaving Alan to wonder if he ever needs to work again.
Jake disappears with the daughter of Charlie's neighbor, a former NFL player (guest star MICHAEL CLARKE DUNCAN), and Charlie is left to cover his back.
Charlies new girlfriend, Chelsea (guest star JENNIFER TAYLOR) asks him to spend the night at her place, while Alan tries to enforce a punishment on Jake.
Alan tries to escape Judiths grasp as Charlie and Herb go on the prowl.
When Judith (series star MARIN HINKLE) kicks Herb (recurring star RYAN STILES) to the curb, Alan comes knocking.
The guys bump into Jake's former teacher, Miss Paternak (guest star ALICIA WITT) who became a stripper after a fling with Charlie. Charlie tries to help her out by giving her a room and a job, but things spiral out of control.
Charlie romances Alans sweet receptionist (guest star KELLY STABLES) as Alan anxiously awaits disaster.
Charlie tries cooking, Alan tries dating two women at the same time and Jake (series star ANGUS T. JONES) tries beer.
Alan (series star JON CRYER) lends Charlie money and crosses a line in his attempts to get it back.
In the sixth season premiere, Charlie encounters an ex-girlfriend (RENA SOFER "24") whose son looks an awful lot like him. MARTIN MULL ("Roseanne") guest stars as Charlie's pharmacist.
The swinging-bachelor lifestyle of commercial-jingle composer -- and chronic gambler -- Charlie Harper (Sheen) was sorely disrupted when his Malibu beach house was invaded by his uptight brother, Alan (Cryer), and Alan's ten-year-old son, Jake (Jones). Given the childish hedonism of Charlie and the domestic immaturity of the soon-to-be-divorced Alan, young Jake turned out to be the true "grown-up" in the Harper household.
Charlie tries to resist temptation when he meets the grown daughter of the woman he's dating (SUSAN BLAKELY) and realizes they've met before. JANE LYNCH guest stars as Dr. Freeman.
Charlie finds himself attracted to Angie (recurring guest star SUSAN BLAKELY), an older woman who writes self-help books. Meanwhile, Alan and Jake battle over a school assignment.
A CSI team investigates a mysterious death at Charlie's house. George Eads ("CSI: Crime Scene Investigation") makes a cameo appearance.
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.
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