During her flight to Chicago, Jessie is eager to “be home again” (246), expecting her relationship with Scar to be just as it was two months ago. Once Scar picks her up at the airport, however, Jessie senses a change in their dynamic. When Jessie compliments her new hairstyle, Scar explains that she “needed a change” (248).

At their favorite pizza place, Jessie explains everything that she has experienced in LA, looking for advice. Scar does not have much to say and reminds Jessie that this time has also been difficult for her. Jessie realizes: “Until now, it has never once occurred to me that my leaving happened to anyone but me” (250), but the two drop the subject, and Jessie suddenly regrets coming to Chicago.

They spend the evening with Scar's new friends in the Schwartz's basement, where the group interrogates Jessie about her new life in LA. She worries that all her complaints to Scar might have sounded like “humblebragging,” even though “the stuff that makes Wood Valley sound interesting and cool is exactly what makes it so lonely” (253). Drunk and lonely while Scar and her love interest, Adam, sneak off, Jessie texts SN and brings up her failed date with Caleb.