This collection consists of a diary maintained by Olivia Tutwiler (later Olivia Tutwiler Hill), a young teacher living in Blacksburg and Childress, Virginia, during the first two months of 1919. The diary begins with January 1, finding Tutwiler in Blacksburg, perhaps during her school's winter break, living at home with her parents. The diary entries are overwhelmingly concerned with Tutwiler's crush on an unidentified cadet at the nearby Virginia Polytechnic Institute, and the entries are addressed to him as "dear boy." The diarist writes often of her love for the cadet, while complaining of his lack of consideration and of her frustration in trying to win his affection. She also mentions a number of other cadets and young men, several of whom are pursuing her, but in whom she has little interest. (Mentioned only a couple of times in passing is the name "Bunker," being Henry "Bunker" Hill, whom Olivia Tutwiler would eventually marry.)

Interspersed within these entries are details of Tutwiler's activities: while staying in Blacksburg, she picks up extra employment by performing clerical duties at the nearby Virginia Cooperative Extension. She also mentions a number of social activities--attending university basketball games and dances, throwing a birthday party, frequently making candy--and discusses the movies she sees and the books she reads. Occasionally, her entries touch on some of the larger issues of the day, mentioning people who have fallen victim to the influenza epidemic of that year and acquaintances who have shipped overseas for service in the war.

By February 3, Tutwiler is again living and teaching in the Childress community (but returns at least twice to Blacksburg), and she mentions her local acquaintances, sometimes relaying gossip. She frequently describes the weather and road conditions. She also makes mention of some of the problems she encounters as a teacher, frequently complaining of her students' lack of knowledge and discipline. The entries end with March 4, 1919.