Herzog writes a fake letter to the governor and then writes a letter to Ramona, telling her not to feel bad because he decided to take a vacation without her. Part of him wants to run into her arms and marry her, but the other part realizes that he's just lonely and desperate.
Herzog's next letter apologizes to a man named Shapiro, who apparently wrote a book on Romanticism that Herzog took forever to review while he was in Europe.
Shapiro visited Herzog once, but quickly became more interested in talking to Madeleine than Herzog. He was overwhelmed by Madeleine's beauty and her knowledge of Eastern European books and languages. The two of them talked about culture and art endlessly while Herzog listened. The truth is that Herzog didn't like the way Shapiro acted (too cocky) and he took it out on Shapiro's work, which was actually good.
Herzog forgets about Shapiro so he can write a letter to his brother Shura asking for five hundred dollars. It looks like the divorce has left him strapped for cash. He also asks whether his brother can recommend a lawyer for him in his ongoing legal issues (i.e. the divorce).
Herzog writes a letter to Sandor Himmelstein, the lawyer from Chicago who he stayed with after Madeleine put him out of their house. This was back before Herzog knew about Madeleine and Val's affair. Sandor is a realist who won't say things just to make a person feel better. He gives Herzog tough love and tells him exactly what to do to minimize the damage this divorce will do on his life.
In retrospect, Herzog realizes that Sandor (like Dr. Edvig) was just another pawn Madeleine used to convince Herzog to give her the settlement she wanted.
Herzog finally arrives at his destination—the home of an old friend named Libby. Libby comes out to meet him and shows him into the house. But as soon as he's alone, Herzog decides that this trip was a mistake. He takes his suitcase and leaves a note for Libby saying he had to go. By eleven o'clock that same night, he's lying in his own bed.
Before going to sleep, Herzog opens an old letter that Lucas Asphalter gave him back in the day. It's a letter from Madeleine's nanny, Geraldine Portnoy, who tells Herzog all about the affair between Madeleine and Val. The letter ends with a concerning detail about Val locking Herzog's daughter June in a car late at night so he (Val) could have a loud fight with Madeleine in private. Herzog feels a bolt of murderous rage when he reads this.