本剧故事发生在一家乡村俱乐部里，是网球版《疯狂高尔夫》（Caddyshack）。1985年夏天，20出头的年轻人David Myers在位于新泽西州的犹太红橡树乡村俱乐部里谋得一份职业网球助理的工作，他试图通过这份工作来确定自己究竟想要怎样的生活。Richard Kind扮演David的父亲Sam Myers，他一直希望儿子能成为一名会计师。在一次心脏病发作之后，Sam确信自己不久于人世，于是将一些惊人的秘密告诉了David。从此以后，这对父子的关系变得十分尴尬。
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.
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.
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.
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