Alan has a surprising inspiration when he mulls making a commitment to Lyndsey; Walden enjoys the attention of a wealthy older woman.
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.
Alan helps Walden develop an alias to find a woman who doesn't just love him for his money.
Alan is alone for Christmas, while Walden continues to play his poorer alter ego.
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.
Walden is ready to tell Kate the truth about his identity when he and Alan go to her fashion show in New York.
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.
Alan is alarmed when Jake brings his thirtysomething girlfriend home for a visit; Walden tries to keep a secret from Alan.
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.
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.
Alan moves in with Herb after he has a fight with Walden.
Walden and Alan's attempt to take Herb's mind off his loneliness gets out of control when they party too hard.
Jake cheats on his girlfriend, Tammy, with her 18-year-old daughter, and the brouhaha that erupts doesn't spare Alan or Walden.
Lyndsey's breakup with Alan leaves him crushed, so Walden tries to lift his spirits and help him get back on his feet.
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