A New York executive, decides to drop everything while visiting his parents (George Segal and Jessica Walter) in Florida, and move into their retirement community. The move prompts his parents to make an unexpected life decision as well.

Alan becomes jealous as David develops a budding relationship with Elaine's new boyfriend, an astronaut (John Hurley).

Elaine and Alan battle for David's affections by buying him fancy gifts.

David becomes the community's matchmaker and reaps the financial rewards with his number one escort, his father.

In an effort to stop his mother from meddling in his dating life, David tells a lie that snowballs out of control.

All is well in David's life until his parents go head-to-head for the neighborhood board seat and take dirty politics to another level.

Alan hits Elaine with a golf cart, but puts the blame on David. Meanwhile, David takes advantage of Elaine's empty apartment and plans a romantic dinner for Jessica.

Alan sets David up with some job interviews in an effort to build his confidence, but makes matters worse when David strikes out on all of them.

It's Alan & Elaine's anniversary and the newly separated couple don't know how to handle it. David decides to come clean to Jessica about his one-night stand.