Set in 1985, high-school graduate David Myers takes a job as an assistant tennis instructor at the predominantly Jewish Red Oaks country club to find out what kind of life he wants for himself. While David makes friends with his tennis supervisor Nash, he inadvertently makes an enemy out of Mr. Getty, the snobbish and arrogant president of the club when David beats him at a grudge tennis match. Meanwhile, David's father Sam is recovering from a heart attack at the hospital in which both he and David's mother Judy flirt with the attractive Korean nurse. David's girlfriend Karen, who works as the aerobics instructor, is persuaded by a sleazy photographer who tries to recruit her to be his model. Also, slacker/stoner parking valet Wheeler tries to pick-up the hot golf instructor Misty. David also learns that the mysterious young woman ogling him is Mr. Getty's daughter. Written by Larry B.

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. Written by Anonymous

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.

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. Written by Anonymous

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. Written by Anonymous

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.