Rose’s third chapter, “Entering the Conversation,” focuses on his four years as an undergraduate at Loyola Marymount University. After MacFarland helps get him admitted, Rose moves into a small apartment with one of his Mercy High classmates, John Connor, who was also starting at Loyola in the fall. The two choose classes based on MacFarland’s recommendations, and they immediately find themselves out of their depth. Rose—who was already only provisionally admitted—is floundering, but he does not reach out for help because he “felt stupid for telling them I was…well—stupid” (43). Instead, Rose “fortified” himself “with defiance,” and he spends his free time scoffing at what he and John dub “the Loyola man,” or the preppy, well-to-do, run-of-the-mill Loyola student (44).

Rose is in a precarious academic position by the end of his freshman year. His grades are close to dipping below a C average, which would violate the terms of his provisional acceptance and get him expelled from school. Rose’s problems are also compounded by deep personal tragedy—Lou Minton, the man who had helped care for Rose’s ailing father and had become a member of Rose’s family—commits suicide after having an argument with Rose’s mother. Luckily for Rose, he had kept in touch with MacFarland, who reaches out to his old connections at Loyola.