While Moehringer tried to be optimistic about his second year at Yale, he felt burdened by both social and academic pressure. Moehringer remembers the efforts he made to be accepted by his classmates and claims that he felt more included by his peers when drinking at the bars than in the classroom. He continued to experience financial constraints, and he struggled to find good work. As a result, the author began his own business laundering wealthy students’ clothes. The author recounts his experience of falling in love with one of his friends’ girlfriends, a student named Sidney, whom he quickly began dating.

As in the rest of his Yale experience, Moehringer was conscious of his and Sidney’s different backgrounds. Unlike his family, Sidney’s parents were still married and ran a successful construction business together. Moehringer remembers that although Sidney had multiple boyfriends at this time, Moehringer was extremely infatuated with her and even suggested that they marry. Sidney, however, remained ambivalent about the relationship, and Moehringer repressed the full extent of his feelings for her. The author recalls his relief at both passing his second-year classes at Yale and not losing Sidney as his girlfriend. Moreover, he was pleased that she had promised him he was her only boyfriend at that point, and he introduced her to his family and the Publicans community.