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.

It's summer '86 and life hasn't gotten any easier for the misfit staffers and clueless members of Red Oaks Country Club. David is caught in the crossfire between girlfriend Skye and her father Getty. Ex-spouses Sam and Judy brave the Jersey singles scene. Nash sets his romantic sights on a rich widow. And resident stoner Wheeler tries to break out of the "friend zone" with lifelong crush Misty.