Lolita is now fourteen, and Humbert is constantly tormented by worry that she may fall in love. In order to learn what he is supposed to do, he reads newspaper articles directed at fathers of teenagers. The articles admonish him not to think of his daughter as a little girl, but as a growing young woman who needs fun and freedom. A good father is supposedly friendly toward his daughters’ boyfriends, chatting with them and trying not to seem like “an old ogre.”

Humbert dismisses this advice and decides to be an ogre. He tells Lolita that she may not, under any circumstances, go out on dates, attend co-ed parties at friends’ houses, talk with boys on the phone, or otherwise engage in potentially romantic encounters. He knows that he must allow her to take part in a few normal activities, so he lets her go places with female friends. He also allows her to chat with boys in public—as long as he is nearby in his car, waiting and watching over her. Under pressure, he also makes a promise to let her throw a co-ed party at home.

Lolita furiously fights Humbert’s restrictions against her dating life. At first he is insanely jealous about this, but ultimately he realizes that Lolita has no particular love interests; she is only objecting because she feels entitled to certain freedoms as she grows up. He muses that children, especially girls, are conservative people who want to behave like their friends do.

Humbert does not get to spend every waking moment with Lolita, so he cannot be certain that she never sees any boys. No matter how strict he is, there are moments when she disappears for a short time, only to turn up and give him “over-elaborate explanations” for her absence. However, he definitely gets the impression that she is too experienced to be impressed by the clumsy advances of teenagers. Because of this, he has no special animosity toward the particular boys he sees talking to her. He just prohibits her generally from the greater danger of romantic relationships that do not involve him.

For safety's sake, Humbert works hard to appear to be the staid, boring European father of a motherless girl. In between his glorious sessions of sexual amusement, he watches himself going through the motions of ordinary life. He works in the college library, goes grocery shopping, goes out to dinner, and shovels snow—always dressed immaculately and behaving with utmost propriety.