Jake cheats on his girlfriend, Tammy, with her 18-year-old daughter, and the brouhaha that erupts doesn't spare Alan or Walden.
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Walden and Alan's attempt to take Herb's mind off his loneliness gets out of control when they party too hard.
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Alan moves in with Herb after he has a fight with Walden.
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Walden runs into his ex-wife, Bridget, at a singles event, and their conversation turns to reconciliation, but Alan worries that they're no longer compatible.
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Walden pleads with Kate to give their romance another shot when he's lonely on Valentine's Day. Meanwhile, Alan's holiday with Lyndsey doesn't proceed as he'd hoped.
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Alan is alarmed when Jake brings his thirtysomething girlfriend home for a visit; Walden tries to keep a secret from Alan.
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Lyndsey is miffed when Alan won't give her a key to the beach house, so she decides to go on a date with a gynecologist. Meanwhile, Alan, Walden, Herb and Billy trade tales of their romantic woes.
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Walden is ready to tell Kate the truth about his identity when he and Alan go to her fashion show in New York.
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Alan makes an investment in Kate's fashion line—using Walden's money. Meanwhile, Walden's double life as a poor man begins to wear on him.
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Alan is alone for Christmas, while Walden continues to play his poorer alter ego.
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Alan helps Walden develop an alias to find a woman who doesn't just love him for his money.
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Alan is surprised that his second ex-wife, Kandi, wants him back in her life. Meanwhile, Walden tries to make Berta's birthday special when she would rather not acknowledge it.
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Alan has a surprising inspiration when he mulls making a commitment to Lyndsey; Walden enjoys the attention of a wealthy older woman.
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Walden hires an actress to be his girlfriend when he tires of the ups and downs of traditional relationships. Meanwhile, Missi and Jake make plans for a rendezvous at the beach house.
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Walden has a romantic dilemma involving a choice between Rose and Zoey.
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Walden begins dating Rose—who was in Paris the day Charlie died—much to Alan's dismay.
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A visit from a friend's daughter makes Walden feel his age.
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Alan and Lyndsey vow to liven up their sex life.
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Walden's mental health deteriorates after his breakup with Zoey.
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Walden gets a hand from singer Michael Bolton in the Season 10 premiere when he makes big plans to surprise Zoey on her birthday.
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