Photographs of Fitzgerald amongst his classmates in grade school and prep school. He also kept pictures of the town he stayed in, his friends and "rivals," and even a woman's lock of hair, her significance to him no longer known.

Francis Scott Key Fitzgerald, commonly referred to simply as Scott Fitzgerald, was raised in Minnesota. Being a “St. Paul boy” in his teens, for the rest of his life Fitzgerald would continue to be referred to as a “St. Paul man.” He went to preparatory school in Hackensack, New Jersey and from there to Princeton University and it was during this stretch of time when he began to show his classmates his tremendous ability to write. This demonstration was not through novels or even short stories initially, but rather through his writings for the stage. Fitzgerald’s comedy “Coward” was being performed in local amateur theaters while he was in prep school and at Princeton he rapidly rose to prominence in the Triangle Club, which produced an original musical every year. In his freshman year, Fitzgerald wrote all of the lyrics for “Fie! Fie! Fi-Fi!” When the Club took its customary winter break tour, newspapers from New York to Cincinnati reported on the show's success. He would go on to write all of the lyrics for the next two Triangle Club productions, the only person in Club history to solely author the lyrics for three years' shows. In addition to his enormously successful plays, Fitzgerald contributed short stories and poems to campus publications, garnering him a reputation as a prolific writer, though he ultimately failed to graduate.

Fitzgerald's memorabilia of his last days of high school before going off to Princeton, including a dance card. His prep school football team is immortalized in a photo from 1912, as is a poem he wrote to a young woman named May.

Princeton provided Fitzgerald with the milieu for his first novel, This Side of Paradise. However, the book was not written from within the walls of a Princeton library. The aftermath of World War I had interrupted Fitzgerald’s education. Dropping out of Princeton, he volunteered for the U.S. Army, and while stationed in Alabama, he met Zelda Sayre, who would eventually become his wife. Her larger-than-life Southern belle personality, combined with his reputation as a performer, would contribute to the stories that were to form about the Fitzgeralds following the publication of his novels.

Memories from Princeton: Fitzgerald kept his report cards, invitations to events, and clippings on his successes with musical and literary clubs. Also see a playbill for "Fie! Fie! Fi-fi!," his first Triangle Club play, and an article acclaiming it.