20-year-old David Myers takes a job as an assistant tennis pro at the predominantly Jewish Red Oaks country club in New Jersey and tries to figure out what kind of life he wants to lead.

David talks Barry into hiring him to film a wedding at Red Oaks. While the club comes out to celebrate, Nash squares off with a rival to impress the father of the bride, and Wheeler ponders an eccentric stranger's business proposition.

David's romantic plans for Karen's birthday go awry, while Sam and Judy's marriage counselors give them a new "empathy" drug to tap into their romantic feelings, and Misty sets Wheeler up on the world's worst blind date.

A mysterious Japanese liquor gives David and Sam an intimate glimpse into each other's lives.

David and Skye ponder their respective futures, both romantic and professional, as they spend an evening in New York City. Wheeler and Misty spend the night driving around town and discussing life.

David's tensions with Barry, his recent night out with Skye, and his growing distance from Karen all threaten to derail a Red Oaks bar mitzvah he's been hired to film. All while Wheeler scrambles to recover a missing package of cocaine.

As the end of summer approaches, David coaches Getty for the Red Oaks tennis championship, and the Red Oaks staff say their goodbyes. But there are big changes coming for the Meyers and the Gettys.