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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.
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.
Because his relationship with Sasha has gone to the next level, Gary must now decide if he should put his career on the line to date his boss or if it's not worth it. Meanwhile, Allison tries to teach Tom a lesson in responsibility.