The author begins Chapter 38 by reflecting on his post-Sidney romantic relationships. Although he met a young woman, Michelle, whom he really liked, he did not feel he was good enough for her, and he thought it was an “act of kindness” to her to not be in her life (309). Instead, he pursued casual relationships with women at Publicans, though never committing to an exclusive relationship. At around this time, an old friend informed him that Sidney was getting married—news that sickened Moehringer. He was happy, however, to hear rumors that he was going to be promoted at the Times. Unfortunately, one editor's vote of disapproval was enough to prevent this advancement, and Moehringer was devastated to learn that he would not get a reporter job after all.

At this time, he moved back into his grandfather’s house, where his cousin McGraw was spending the summer. Unfortunately, McGraw was considering quitting his baseball career, which enraged his mother, Ruth, and Moehringer and McGraw spent most of the summer at Publicans to hide from her constant abuse. Moehringer was again depressed and discouraged about his career and wanted to escape Manhasset and backpack around Ireland with McGraw. He and McGraw tried gambling on horse racing and poker to raise enough money to travel, though with little success.