In the second-season finale, told through flashbacks as Jake reads a report to his class, an angry husband (Orson Bean) confronts Charlie for sleeping with his wife. Natalie: Karen Trella. Teacher: Patricia Bethune. Jake: Angus T. Jones.
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A women's volleyball team walks into a bar. It's no joke, but a godsend for Alan and Charlie, who are drinking away the guilt of letting Jake stay with Evelyn. Danielle: Catherine McCord. Kimberly: Christina Chambers. Evelyn: Holland Taylor. Jake: Angus T. Jones.
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Alan foolishly borrows money from Evelyn to buy a Porsche, and in turn she asks him to go on a blind date with the daughter (Chloe Webb) of a man she's dating. Cab Driver: Jay Harik. Waiter: John O'Brien.
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Alan, Jake and a reluctant Charlie accompany Evelyn to the funeral of one of her ex-husbands, and Charlie starts hitting on the young and beautiful widow (Cynthia Preston). Christine: Gigi Rice. Minister: Steve Tom. Evelyn: Holland Taylor.
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When Charlie and Alan antagonize each other like adolescent boys, Rose gets them to sit down and discuss their unresolved issues. Rose: Melanie Lynskey. Berta: Conchata Ferrell. Jake: Angus T. Jones. Judith: Marin Hinkle.
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A bold Alan asks out Sherri (Jeri Ryan), who was indifferent to Charlie when they dated, and, to everyone's surprise, she's attracted to Alan. Stephan: James Edson. Jake: Angus T. Jones. Alan: Jon Cryer. Charlie: Charlie Sheen.
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Charlie persuades Alan to pretend they're a couple to impress a gay ad-agency exec, then has a dilemma when he falls for the man's gorgeous ex-wife (Lucy Lawless). Eric: David Starzyk. Evelyn: Holland Taylor. Rose: Melanie Lynskey.
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A wild night of pleasure leaves Charlie in severe back pain, but it's not enough to keep him from hitting on his beautiful doctor (Alicia Coppola), which appalls Alan. Debbie: Kristen Miller. Male Nurse: Ken Jeong. Nurse: Helen Greenberg.
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Judith goes to Hawaii, leaving Jake with Alan and Charlie for an entire week, and everything that can go wrong does for all three...er...two and a half men. Jake: Angus T. Jones. Berta: Conchata Ferrell. Alan Jon Cryer.
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Worried over getting a colonoscopy, Alan takes Charlie's advice to go with him to Las Vegas and to bring Jake. But obstacles keep delaying the outing, including Jake getting sick. Anesthesiologist: Suzanne Whang. Doctor: Mark Chaet. Jake: Angus T. Jones.
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Evelyn pushes Alan too far when she crushes Jake's self-esteem, and he tells her she's no longer allowed to see her grandson. Dr. Little: Bob Morrisey. Evelyn: Holland Taylor. Jake: Angus T. Jones. Judith: Marin Hinkle.
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When a water pipe breaks in Judith's home, flooding the house, Alan invites her to stay at Charlie's until the repairs are finished, but when she goes on a date while staying there, he regrets his kindness. Camille: Nicole Forester. Svetlana: Magdalena Zielinska.
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A high-school friend (Paget Brewster) visits Alan, who is awed by how beautiful she's become; and the transformation doesn't escape Charlie's notice either. Jake: Angus T. Jones.
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Charlie learns that there is a Web site devoted to trashing him and his womanizing ways. Meanwhile, Alan mistakenly thinks Judith wants to get back together with him. Gail: Jodi Lyn O'Keefe.
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Alan and Rose begin a surprisingly close friendship that could become something more. Meanwhile, Charlie tries to compose a theme song for a cartoon based on a comic book. Rose: Melanie Lynskey. Jake: Angus T. Jones.
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Charlie's old flame Lisa (Denise Richards) returns. She's no longer married, but has a child for whom Charlie feigns interest in order to win over Lisa. The couple's real-life daughter appears as the infant. Megan: Audrey Wasilewski. Berta: Conchata Ferrell. Jake: Angus T. Jones.
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In a strange reversal for the brothers, Alan meets a woman (Kelley West) at the supermarket who releases his uninhibited wild side. Evelyn: Holland Taylor. Judith: Marin Hinkle. Jake: Angus T. Jones.
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Charlie and Alan hire Berta's disturbed sister (Camryn Manheim) as a caterer after Evelyn guilts them into throwing a party for her. Berta: Conchata Ferrell. Evelyn: Holland Taylor. Judith: Marin Hinkle. Alan: Jon Cryer.
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A guilt-riddled Charlie confesses he did something to Alan when they were kids that has affected Alan's life negatively. Rose: Melanie Lynskey. Evelyn: Holland Taylor. Jake: Angus T. Jones.
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Charlie meets his match in a self-centered woman (Jeri Ryan) who takes control of the relationship and treats him the same way he usually treats his dates. Alan: Jon Cryer. Berta: Conchata Ferrell. Jake: Angus T. Jones.
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Charlie trades cars with his mother so that she can impress a client with his Mercedes, but later regrets his decision when he learns how she used his vehicle; Alan is bothered that Jake seems to like Judith's new boyfriend more than him just because the man has a boat and a pool. Judith: Marin Hinkle. Alan: Jon Cryer. Jake: Angus T. Jones.
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Jake could be suspended for making an obscene gesture at school, but Charlie thinks he has a way to fix things with the teacher (Missi Pyle) in order to keep her from punishing the boy. Judith: Marin Hinkle. Alan: Jon Cryer. Jake: Angus T. Jones.
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Alan is shocked to learn that Jake's pediatrician (Ryan Stiles) is sleeping with Judith; while Evelyn confronts Charlie about his hatred for her and is joined by Berta and Rose who demand to know as well. Judith: Marin Hinkle. Evelyn: Holland Taylor. Berta: Conchata Ferrell.
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Sean Penn, Elvis Costello and Harry Dean Stanton appear as themselves in the second-season opener in which Alan is hurt that Charlie excludes him from his regular meeting with his friends, which he refuses to call “a support group.” Coop: Bobby Cooper. Rose: Melanie Lynskey. Judith: Marin Hinkle.
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