Most of the characters are drawn directly from Fitzgerald's own life.[25]
- Amory Blaine – a Princeton alumnus from the Midwest and later a World War I veteran who has a series of unfulfilling romances with young women. The character is based on Fitzgerald and his failed relationships.[26] The name "Amory" is taken from Fitzgerald's football hero at Princeton, Hobart Amory Baker.[27]
- Isabelle Borgé – a wealthy but shallow debutante who becomes Amory's first love.[28] The character is based on Ginevra King,[29] an heiress upon whom Fitzgerald developed a life-long fixation.[28] Like Isabelle and Amory, Fitzgerald met King on Christmas break during his sophomore year at Princeton, and their relationship ended in a similar fashion.[30] Purportedly, "Fitzgerald was so smitten by King that for years he could not think of her without tears coming to his eyes".[31]
- Rosalind Connage – a cruel and selfish flapper who becomes Amory's second love.[32] Rosalind is based on Zelda Sayre and, to a lesser extent, on the fictional character of Beatrice Normandy in H. G. Wells' realist novel Tono-Bungay (1909).[32] Mirroring Rosalind's materialistic relationship with Amory, Sayre initially ended her relationship with Fitzgerald due to his lack of financial prospects and his inability to support her privileged lifestyle as an idle Southern belle.[e][33][34]
- Eleanor Savage – a beautiful 18-year-old atheist whom Amory meets in Maryland.[35] Fitzgerald based Eleanor on Elizabeth Beckwith MacKie, a romantic interest whom he knew briefly.[36][37] MacKie later commented that "the Eleanor he described only reminded me of how little he really knew me. His Eleanor loved to sit on a haystack in the rain reciting poetry. Forgive me, Scott: if that is the way you wanted it, then you missed the whole idea of what can happen atop a haystack."[38] Fitzgerald also partly based Eleanor on a young love of his mentor Father Sigourney Fay.[35]
- Thayer Darcy – a Catholic priest who becomes Amory's spiritual mentor. The character is based on Father Sigourney Fay, Fitzgerald's mentor and confidant.[39] While writing This Side of Paradise, Fitzgerald quoted verbatim entire letters sent to him by Father Sigourney Fay.[40] In addition to using Fay's correspondence, Fitzgerald drew upon anecdotes that Fay had told him about his private life, including his failed romances.[35] When reading This Side of Paradise, Fay wrote to Fitzgerald that the use of his own biographical experiences told in confidence to the young author "gave him a queer feeling."[35]
- Beatrice Blaine – an aging and eccentric matron who is Amory's mother. Based on the mother of one of Fitzgerald's friends.
- Clara Page – a widowed older cousin whom Amory loves, but she doesn't return his affections. Based on Fitzgerald's cousin Cecilia Delihant Taylor.[41]
- Cecilia Connage – Rosalind's cynical younger sister who purloins Rosalind's cigarettes. She is envious of her sister's popularity among young men.[32]
- Allenby – a heroic football captain at Princeton based on Hobey Baker, the legendary Princeton athlete and military aviator who died during World War I.[42]
- Thomas Parke D'Invilliers – a Princeton classmate who has a gift for poetry. He becomes Amory's close friend and confidante of various subjects, among which are literature, love for young beauties, politics and the meaning of the self. D'Invilliers later becomes a journalist, developing his own perspectives as apart from that he shares with Amory. Fitzgerald based D'Invilliers on his friend, poet John Peale Bishop.[43] The character reappears as a fictitious poet in the opening of The Great Gatsby.[43]
