The song "Preppy Boy" by John Grant tells the story of a narrator who is infatuated with a stylish and preppy boy. The lyrics describe the boy's appearance, including his clothing such as cuffed khakis, brown top-siders, and a navy blue polo shirt. The boy is portrayed as confident and sporty, playing lacrosse and wanting to be in charge. The narrator acknowledges the boy's desire for power and success but suggests that the girl he is interested in, referred to as "the girl in the whale skirt," will never understand him. Despite this, the narrator finds the boy attractive and expresses interest in him. The song also touches upon themes of waiting and yearning. The narrator mentions being tired of waiting in line and being unemployed, possibly suggesting a sense of longing for a romantic connection with the preppy boy. The narrator admits that the boy may not be perfect, comparing him to Treat Williams (an actor), but expresses a desire to take a chance with him. Overall, "Preppy Boy" conveys a mixture of admiration, longing, and hope for a potential romantic relationship.
