David takes a freelance job videoing a bris and accepts Getty's invitation to lunch in the city. Back home, Judy enjoys Ladies Night with new friends, while Sam goes on a blind date.

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.

With the pressure of his trial weighing on him, Getty turns to an unusual confidante for moral support. One of Wheeler's students gets a little too close for comfort. And while Skye struggles to find her place on the New York art scene, David and Karen reconnect.

Summer of 1987 finds David Meyers living in New York and working at a video production company. Unfortunately his dreams of becoming a filmmaker-and his love life-are going nowhere fast. Meanwhile at Red Oaks, tennis pro Nash learns alarming news about the future of the country club.

While David angles to get hired to direct a dog food commercial, best friend Wheeler learns of a handsome rival for girlfriend Misty's affections. Nash visits Getty in prison, bringing dire news of a threat to Red Oaks. IRS Agent Terry pitches Sam on a business venture for which neither is qualified.

Wheeler weighs an unusual proposition from his Columbia lit professor. Despite warnings from his ex-wife Judy, Sam decides to go into business with Terry. Getty recruits David to help save his beloved Red Oaks.

Sam and Shirley run into trouble during a night on the town. Following a dressing-down from his boss Derek and a fight with Wheeler, David goes in search of a friendly face.

As summer winds down, it's the end of an era for Red Oaks Country Club - but the start of a bright future for David Meyers and friends.