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.

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.

Troubled by his recent relationship woes, Frasier goes to the country for peace and quiet but ends up facing the ghosts of failed relationships past.

Frasier and Niles compete to see some rare wine, owned by a rich relative of Kirby's girlfriend. Meanwhile, Martin must wear a blood pressure monitor.

Kenny tells Frasier and Roz that some recent research into KACL listeners shows that Frasier's average listener is an older gentleman who keeps the radio on for company. He suggests Frasier reach out to the youth.