While working as a DJ at the school radio station, Alex strikes up a telephone friendship with caller Lorraine Ferrar, who shares his love of swing music, and he and the attractive 40-year-old meet and develop a special relationship.

Drawn to Lorraine's sexy voice and love of swing music, Alex invites her to a Big Band concert. On arriving at her home for the date, he's shocked to find that she's an older woman and the mother of one of his sister's classmates. But they develop a platonic relationship, enjoying each other's company and discovering a wide range of shared interests. When Alex and Lorraine continue to ""date"", Steven and Elyse try to accept it but eventually ask her to stop seeing their son.