In Twenty Boy Summer, Sarah Ockler tells the story of Anna, a girl who embarks with her best friend Frankie on a 20-day trip to Zanzibar Bay, where Frankie decides that they should meet a new boy every day and find their first summer romances. What Anna doesn't tell Frankie is that she already has had a summer fling, and that it was with Frankie's brother, Matt, who tragically died one year before.