While shopping for a DVD player, Frasier meets an attractive woman called Claire. He soon discovers that she is a friend of Lana, former prom queen of his school whom he dated briefly in the past.

In desperation, Frasier cuts a deal with the teenager he's tutoring: he'll get the dimwit a hot date for his school dance if the teen buckles down.

A Caribbean trip turns chaotic as a familiar figure from Frasier's past appears.

Frasier continues to be conflicted about whether he truly wants to be with Lana instead of Claire. He consults his family, but a chance encounter at the airport steers him toward making a decision. Unfortunately, he may be too late.