On the eve of her first day of senior high, May Sutherland’s mother gives her a diary in which to record her experiences. It’s 1948 and the entire student body at Magee High in Vancouver is divided according to their preference for Bing Crosby or Frank Sinatra. After losing her two best friends overnight, May struggles between her disdain for the debate and her loneliness as one of only a handful of neutrals. At home her parents, both university professors, are absorbed in their own work while maintaining the semblance of a happy household. Parked in front of the living-room console, May conducts an extensive comparison of the two singers, only to find her questions one day answered by a different kind of music altogether. The diary entries reveal May’s commitment to being genuine and truthful, and her attempts to match her parents’ poise while passing for a normal teenager in the process.