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.

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.

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.

Getty prepares for his trial on insider trading charges. Nash's romance with Widow Horowitz heats up. Meanwhile, David wonders if he may be too suburban for Skye's new city lifestyle.

Barry recruits David to film his bachelor party jaunt to Atlantic City, and Nash and Wheeler tag along for the most awkward road trip of their lives. Sam and Judy team up to search for his lost cat.

As Karen and Barry prepare to tie the knot, David finds himself grappling with a forlorn Nash, arguing parents, and stark choices for his future.

Getty feels the heat as the jury verdict-and the club recall election-loom. With the summer winding down, Wheeler and Misty confront tough questions about what fall brings. David must define his own independence and make a decision about Getty's lucrative job offer.