Like many first novels, This Side of Paradise is largely autobiographical.

Amory Blaine, the protagonist, is drawn from Fitzgerald's adolescence and young manhood. The narrative follows Blaine from his relatively pampered childhood, where he had a very close relationship to his mother, through the difficulties of adjusting to the outside world in prep school and then on through his development as a "romantic egoist" at Princeton. The years at Princeton represent the first genuinely realistic depiction of American college life, and suggest that life on the campus is exciting and intellectually stimulating. For aspiring collegians, the first part of This Side of Paradise was like a guidebook, offering suggestions about how to behave socially, and some sense of the curriculum, mentioning sixty-four titles and ninety-eight writers. Fitzgerald later called the book "A Romance and a Reading List," and the romantic element included Blaine's unsuccessful courtship of...