Amory Blaine, the son of a wealthy family, is introduced at the beginning of the novel as deeply influenced by his relationship with his mother, Beatrice: a charming, intelligent, but unstable woman. As a result, he considers himself an "aristocratic egotist," acting with a self-involved superior attitude; the name Amory means "brave, powerful leader." Amory has difficulty being liked by his peers and sustaining emotional relationships with girls. Despite his air of confidence, he hungers for social status and popularity and assumes whatever characteristics he believes will help him attain acceptance. At Princeton University, he eventually makes more friends and has many romantic partners, but he still fails to develop much emotional intimacy or self-awareness. Amory enlists as a soldier in World War I. After he returns, he suffers romantic heartbreak, the loss of his family's wealth, and the death of his close friend and father figure, Monsignor Darcy. These events cause Amory to develop a somewhat more mature view of the world and his place in it.
Beatrice, whose name means "blessing," has a close and formative relationship with her son, Amory, in his early childhood, but they grow apart as he grows older, and she sends him away to be educated elsewhere. Their relationship influences the kinds of relationships Amory will have with women as he gets older; Beatrice can be fickle and dramatic, characteristics Amory's lovers often share.
Monsignor Darcy sees Amory as a reflection of himself, and considers Amory to be the son he never had. He offers Amory a great deal of guidance and understanding throughout his young adulthood, and is the person to whom Amory seems to be closest. Amory takes his advice seriously and aims to impress him. Monsignor Darcy's death marks a turning point in Amory's view of himself and his place in the world.
Isabelle, whose name means "devoted to God," is Amory's first love, a girl who he knew from his schoolboy years and is reunited with during his first year at Princeton University. Isabelle is characterized by her judgmental attitude toward Amory. Their love affair is intense but short-lived. Amory is quick to realize he doesn't truly care for Isabelle, while she criticizes him for being egotistical.
Rosalind, whose name means "beautiful rose," seems to affect Amory in a way that none of his lovers before or after her do. Rather than see her as a mirror of himself, Amory feels true love and affection for her. Rosalind is a free-spirited young woman, but she ultimately marries for money, breaking Amory's heart in the process.
Although Amory seems incapable of loving Eleanor (whose name means "bright, shining one") as purely as he loved Rosalind, they are bonded by a shared love of poetry and literature. Yet their romance is also fleeting. Eleanor is high-spirited but ultimately proves dangerously unstable. Their magical summer romance ends when she threatens to ride her horse over a cliff. Amory finds himself ultimately repulsed by her in the same way he has been by other women in the past.
Clara, whose name means "bright or clear," remains an unattainable woman in Amory's life because his charms fail to impress her and she rejects the possibility of a romance with or marriage to him. An intelligent woman, as well as a widow and a mother of two, she radiates empathy and maturity, characteristics the egotistical Amory lacks. Of all the women that Amory has loved, he realizes that she is the only one who truly sees him for who he is.