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When Walden encourages a depressed Alan to update his look and start dating again, Alan faces a moral dilemma when he attracts a married woman.
Alan has trouble coping when Lyndsey dumps him and Walden must find a way to help him get back on his feet.
Walden dates a hot 22-year-old woman, but finds himself more attracted to her worldly grandmother. Meanwhile, Alan and Jake go on a father-son bonding trip.