James "Jimmy" Gualtieri is the son of mobster Paulie Walnuts, a member of the DiMeo family, who was told many times by his father to not be like him in the mob life.

Eventually, Jimmy learns that his father would be in jail and had to drop out of school, collect the money from his after school job, and help get his father out.

While celebrating Paulie's release from jail, he meets Meadow Soprano, the oldest daughter of the Don for the DiMeo Family, Tony Soprano.

After meeting Jimmy, Meadow starts to find him attractive and tries to flirt with him, how does he feel about her?