It's the summer before senior year and 16-year-old Winston Downs has a problem. Okay, maybe it's not a problem exactly. He's just found out he's the subject of a crush. He was not prepared for this. He's not prepared for anything. With less than a year before he's supposed to have everything "figured out", what can Winston do? Winston can write. What starts as a diary of emotions (that may or may not be given to his admirer) becomes a journal featuring explanations of his past, examinations of his present, and expectations of his future.