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.

It's the summer of '87 and change is in the air at Red Oaks. David is chasing his dream to become a director in NYC. Wheeler and Misty have taken their relationship to the next level but face unforeseen obstacles. Getty is making lemonade out of lemons in prison and Sam and Judy are finding new and unexplored passions. Meanwhile, back at Red Oaks, Nash finds that the club's future is in danger.