As he progresses to Princeton University from the Midwest, he experiences a series of flirtations with some predatory young women and a chance at friendship with some intellectual young men. His love-life culminates in a genuine but ill-fated love with a soul-mate who rejects him to marry a wealthier young man.

This Side of Paradise was first published in 1920 and was considered daring and intellectual in its day. Its enormous popularity helped to launch young Fitzgerald's career as a major writer.