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Wheeler weighs an unusual proposition from his Columbia lit professor. Despite warnings from his ex-wife Judy, Sam decides to go into business with Terry. Getty recruits David to help save his beloved Red Oaks.
While David angles to get hired to direct a dog food commercial, best friend Wheeler learns of a handsome rival for girlfriend Misty's affections. Nash visits Getty in prison, bringing dire news of a threat to Red Oaks. IRS Agent Terry pitches Sam on a business venture for which neither is qualified.
Sam and Shirley run into trouble during a night on the town. Following a dressing-down from his boss Derek and a fight with Wheeler, David goes in search of a friendly face.
Summer '87 finds David in the Big Apple, working at a video production company, and striking out with the ladies of New York. Luckily he's got roommate Wheeler to help cheer him up. But Wheeler's got his own problems, with the appearance on the scene of a handsome rival for Misty's affections. Meanwhile Nash brings an incarcerated Getty news of a threat to the future of their beloved Red Oaks.