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.

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.

With Red Oaks' Independence Day party in full swing, Getty enlists David as his coach for the upcoming club tennis championship, and Wheeler catches Misty's boyfriend in a compromising position. Meanwhile, Judy struggles with conflicted feelings for her female yoga teacher.

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.

David is hired to film a sex tape for middle-aged swingers from the club, but the experience isn't quite the stuff of fantasy. Meanwhile, Karen tries her hand at modeling for Barry, and Judy throws a party for the students in her real estate class, to Sam's chagrin.

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.

In the summer of 1985, 20-year-old David Meyers takes a job as a tennis pro at Red Oaks Country Club in suburban New Jersey, as his parents, girlfriend, and co-workers pull him toward a future he's increasingly unsure he wants.

David finds himself swept into a surprising hustle when he agrees to be Getty's doubles partner for an outside-work tennis match. As David gets to know Getty's daughter, Skye, Nash nurtures dreams of playing the stock market, and Wheeler and Misty bond over a parallel parking lesson.

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.

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