At a December meeting at Lolita’s school, Headmistress Pratt tells Humbert that Lolita is misbehaving and using foul language; also, she is not maturing sexually. She uses psychoanalytical terms to explain that Lolita is between the anal and genital phases of development. The application of psychological terms to Lolita upsets Humbert. He grows embarrassed as Pratt continues to suggest that Lolita probably does not understand sex and is subconsciously seeking an outlet. She suggests that Lolita should start dating boys and that she ought to be allowed to act in the school play, The Hunted Enchanters. After leaving the meeting, Humbert goes to visit Lolita in a study room. He finds her sitting with another girl. He pays Lolita 65 cents to masturbate him in exchange for letting her participate in the play. 

Around Christmas, Lolita gets sick. Once she is well, Humbert throws “a Party with Boys” (198). The party goes poorly, as Lolita does not like any of the boys. As a reward, Humbert buys Lolita a new tennis racket. For her birthday, he buys her a book of modern paintings as well as a bike. Lolita does not appreciate art, which disappoints him, especially because her inability to understand art means she cannot appreciate his opinions about art.