In Chapters 17 to 19, Moehringer relays his experiences in high school. He was thrilled to have the opportunity to work at a law firm in Manhattan where his cousin Sheryl also had a job. Sheryl, now in her early twenties, advised Moehringer on her idea of manliness, but her suggestions were limited to superficial considerations such as fashion choices, newspaper brands, and drinking. Sheryl told him to behave like the upper-class men who also commuted from Manhasset to Manhattan. She also encouraged him to drink more frequently and visit bars with her despite being under-aged.

Moehringer continued to miss and worry about his mother frequently during this time. One day, his worst fears were realized when she was hit by a drunk driver and was hospitalized with a severe concussion causing temporary amnesia. Fortunately, his mother returned home from the hospital after a week and sustained no long-term brain damage. Moehringer returned to Arizona to visit his injured mother and, once there, felt lonely and overwhelmed. He sought out his high school crush, Lana, and humorously recounts his first sexual experience with her.

Moehringer had tried for many years to put his father out of his mind, however, by this age, he began looking for him once more.