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Gary tries to help Tom impress a girl by buying a boat, but he gets in over his head and must seek help from Allison's boyfriend.
Gary and Sasha's first date is interrupted by Allison, so Sasha starts to really notice the bad sides of dating a divorced man.
Worrying that Tom may be hanging out with the wrong guys at school, Gary and Allison take it upon themselves to probe into Tom's personal life. Meanwhile, Sasha flirts with professional surfer Laird Hamilton.