Shiloh is one of Rowell’s dual protagonists in the story, and Rowell alternates between Shiloh’s present reality as a single parent raising two young children and her high school self. As a teenager, Shiloh is a rebel, far left leaning in her politics and set on eschewing traditional teenage rituals like senior prom. An unapologetic misanthrope, Shiloh doesn’t enjoy being in large groups and prefers the company of her best friends, Mikey and Cary. Shiloh and Cary share a unique bond as they live in the same under resourced part of Omaha, and they spend a lot of time together since Cary drives Shiloh to school daily. Though she doesn’t realize it then, Shiloh is in love with Cary in high school, but she lacks the confidence and self-acceptance to act upon her attraction. Aside from constantly touching him, Shiloh gives no indication she loves him, and Cary never tells her he feels the same. When they finally act on their mutual attraction in college, Cary is on the precipice of military deployment, and Shiloh downplays their connection, pushes him away out of self-preservation, foreshadowing the ways in which The Enduring Power of First Love catalyzes Shiloh’s personal growth over the course of the novel.