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In the seventh season, he begins a relationship with Lyndsey Mc Elroy (Courtney Thorne-Smith), the mother of one of Jake's friends.Their relationship is temporarily suspended when Alan cheats on her and accidentally burns down her house, but the relationship eventually resumes.He needs friends and the three form a tightknit surrogate family.At the end of the ninth season, Jake joins the United States Army; he appears occasionally during season 10, briefly dating Tammy (Jaime Pressly), who is 17 years his senior and has three kids, as well as Tammy's daughter Ashley (Emily Osment).In the ninth-season premiere (after Charlie's death), the beach house is sold to Walden Schmidt (Ashton Kutcher), an Internet billionaire going through a divorce from Bridget (Judy Greer).

After Alan divorces, he moves with his son to share Charlie's beachfront Malibu house and complicates Charlie's freewheeling life. Television reached a multiyear broadcasting agreement for the series, renewing it through at least the 2011–12 season. decided to end production for the rest of the eighth season after Sheen entered drug rehabilitation and made "disparaging comments" about the series' creator and executive producer Chuck Lorre.They later break up when he reveals who he really is, though Kate realizes that Walden's money helped her become a successful clothing designer.Jake announces he is being shipped to Japan for a year, so Alan and he go on a father-son bonding trip.The first five seasons find Charlie in casual sexual relationships with numerous women until the sixth season, when he becomes engaged to Chelsea (Jennifer Taylor), but the relationship does not last as Chelsea breaks off their engagement.Afterwards, Charlie flies to Paris in the eighth-season finale with his stalker Rose.

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