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.
A newly-paroled Getty makes a last-ditch effort to save Red Oaks from the wrecking ball. Sam's side business is dealt a major setback. Misty and Wheeler separately fend off unwanted advances. And David finally makes a decision he should have months ago.