After Humbert’s residency at Catnip College, he and Rita return to New York. Their apartment there has a mailbox with a glass slit in it. The light often falls through this piece of glass in such a way as to distort the handwriting on the letters that await him. Because of this, he often convinces himself briefly that he is seeing Lolita’s “lovely, loopy, childish scrawl” on the envelopes. This causes him to feel many false flashes of hope.

When Lolita finally does write to Humbert, he does not immediately realize it. He happens to grab the mail out of the mailbox in the midst of an argument with the janitor, who is complaining about a male friend of Rita’s who recently vomited on the stairs. Distracted by this conversation, Humbert wrongly dismisses one of the envelopes as a boring note from Rita's mother. He opens the other envelope, which comes from his friend and lawyer, John Farlow.

Humbert is surprised when he sees that John's letter is rambling and somewhat shrill. John has always been a staid and dependable man, and he has handled Charlotte’s monetary affairs since her death. Now, however, his wife has died, and he has re-married and moved to South America. He says that he is no longer willing to handle Charlotte's money. He has heard a rumor that Lolita has disappeared and that Humbert is now living with “a notorious divorcee.” Humbert reads the letter and tosses it aside in disgust, annoyed that people have been talking about him and that John's personality has changed over the years. In Humbert's opinion, people should stay the same forever rather than inconveniencing their friends by going through annoying transformations. This is one of the reason Humbert likes books; his favorite book characters behave in the same ways no matter how often he re-reads their stories.

Next, Humbert turns to the other letter. He is shocked when he sees that it is from Lolita. She addresses him as “Dad” and says simply that she is married and pregnant. Her husband, Dick, has an excellent job offer in Alaska, but they do not have enough money to move. She asks Humbert for a few hundred dollars to help her get out of the town where she currently lives—a dirty place where “you can’t see the morons for the smog.” She refuses to give Humbert her home address, asking him instead to write her at her town’s post office. She concludes with the words: “I have gone through much sadness and hardship.”