As they continue heading west, Humbert becomes increasingly paranoid. One day, Humbert catches Lolita talking to a strange man, who resembles Humbert’s relative Gustave Trapp. Lolita says she was simply giving him directions and shrugs off Humbert’s suspicions. On the road the next day, Humbert suspects they’re being followed by a red car but manages to evade it. Lolita says she has misread the tour book, and by mistake they find themselves at a theater, watching a play written by Clare Quilty and Vivian Darkbloom. Humbert is suspicious about the play’s authors but cannot see them well in the shadows. When questioned, Lolita states that Vivian is actually a man and Clare is the female author of The Enchanted Hunters. Humbert recalls that Lolita used to have a crush on the celebrity Clare Quilty, but Lolita laughs off the idea.
At the post office, Humbert reads a letter to Lolita from Mona, who describes the school production of The Enchanted Hunters. When he finishes the letter, he realizes that Lolita has disappeared. Humbert chases after her, and when he finds her, Lolita says she had seen one of her friends from Beardsley. Humbert interrogates her vigorously, but she does not budge in her story. Humbert tells Lolita that he has written down the license plate number of the car following them, but he discovers that Lolita has erased the number and smacks her for it. Later, Humbert realizes that the man following him—whom he has taken to calling Trapp, after Humbert’s Swiss relative, whom the man resembles—has been switching cars. When Humbert’s car gets a flat tire, Trapp stops not far behind them. Humbert gets out of the car to confront him, but Trapp turns and speeds away while Humbert’s car, with Lolita at the wheel, starts moving. Lolita claims that she was trying to stop the car from rolling away. Humbert begins to keep the gun in his pocket.
Despite believing that Lolita’s acting experience has taught her to be deceitful, Humbert fondly remembers watching her go through her drama exercises. However, that thrill doesn’t compare to the joy he feels while watching Lolita play tennis. Humbert goes on at length, describing how maddeningly attractive Lolita is on the tennis courts. He admits that he finds all kinds of games romantic and magical, including his chess games with Gaston. In the middle of one tennis game, at a hotel in Colorado, Humbert receives an urgent note that the Beardsley School has called. However, Humbert realizes that the school would have no way of getting in touch with him there. From a window in the hotel, Humbert looks back to the tennis court and sees a strange man playing doubles with Lolita. By the time Humbert returns, the man has left and neither Lolita nor the other doubles pair will tell him about the mysterious stranger. Lolita tells him she wants to go swimming.
Later, at the pool, Humbert sees a dark-haired man watching Lolita lasciviously. He sees that Lolita can tell the man is watching her, and he watches as Lolita flirts with the man from afar. Humbert recognizes him as Trapp, the man who has been following them, but Trapp disappears before Humbert can confront him. Humbert drinks heavily and starts to wonder if he’s imagining Trapp.
Later that night, Lolita claims to be ill. Seeing that she has a high fever, Humbert takes her to the hospital. He stays in a nearby motel, separated from Lolita for the first time in two years. Lolita recovers quickly, and Humbert visits her in the hospital, bringing presents. He sees a letter on Lolita’s bed tray, but the nurse insists that it belongs to her, not Lolita. Later, Humbert himself becomes feverish, but he tells the hospital he’ll pick up Lolita the following day. However, when he arrives at the hospital, the doctors inform him that Lolita has already left with her uncle. Humbert goes into a violent rage but manages to get himself out of the hospital. He vows to kill Lolita’s abductor.
In this section, the novel begins to resemble a traditional crime novel and detective story. As in the gangster movies Lolita adores, Humbert and Lolita find themselves pursued by mysterious cars and strange, shadowy men. Humbert begins to fall into the role of a film noir protagonist, adopting the appropriate language and habits, drinking heavily and calling his gun his “chum.” Both the reader and Humbert find themselves awash in clues, but many of those clues will end up as nothing more than red herrings, or dead ends. The combination of Humbert’s paranoia, the mysterious cars, and Lolita’s inexplicable absences make Humbert’s situation seem dire indeed. The more Humbert tries to prevent the inevitable, the less control he has over Lolita—or even himself. Despairing, he turns to violence, hoping to eliminate his mounting sense of dread by eliminating his shadowy pursuer, whom he refers to as “Trapp,” with a pun on “trap” that is all too appropriate to Humbert’s situation. Humbert’s paranoia can be attributed, in part, to this shift in the narrative’s genre. Humbert considers himself an aesthete, an intellectual, and a romantic. He enjoys styling himself the hero in a love story, but he’s profoundly unsuited to the role of gumshoe in a hard-boiled thriller.