In this chapter, Obama recounts his last years of high school at Punahou. The chapter opens as Obama listens to and argues with Ray, his best friend and an African-American native of Los Angeles, about racism and the difficulty of dating. While it is clear to Ray that many of his difficulties stem from racism, Obama insists that race doesn't explain everything.

Obama admits to himself that life in the five years since his father's visit "had gotten complicated" (74) despite the improvements in Obama's social status at school. Ann enrolls in an anthropology master's program in Hawaii and struggles to support her family on her stipend; she lets Obama know early on that graduate school, not traditional mothering, is her priority. Obama helps out as much as he can, but when Ann returns to Indonesia (taking Maya with her) to do research for her degree, Obama moves back in with his grandparents.

Obama's major struggle during these years is to understand how to be black and a man in America. He has few models. His father's only presence in his life are letters filled with cryptic sayings about how he should conduct himself. The black men Obama encounters are Gramps's friends—bridge partners, an old poet—and the men Obama encounters when Gramps takes him to a bar down in the sex work district in Honolulu.