One day, Headmistress Pratt calls Humbert Humbert in to discuss Lolita’s worrying behavior at school. She is worried that Lolita is sexually and socially repressed, and that her father’s strictness about dating and socializing might have something to do with it. Chalking up this behavior to Humbert’s being an “old-fashioned Continental father,” she urges him to loosen his restrictions on her behavior. In particular, Pratt asks Humbert to let Lolita participate in the school play, a production of The Enchanted Hunters. Humbert agrees, frightened that Pratt has noticed something wrong with Lolita. Before leaving the school, he visits Lolita in class, where he pays her a few cents for a hand-job. He is later shocked by his boldness in taking such a huge risk.
Here, we get a glimpse of the damage Humbert has done to Lolita. By abusing her, he has turned her into an outsider, a social misfit like himself. The reappearance of the name “The Enchanted Hunters,”—the motel where Humbert first raped Lolita—should put us on our guard. Something with great importance for Humbert’s fate is about to take place. We can speculate from his previous behavior that Humbert might be aroused by knowing he is on the brink of getting caught.