Diana O’Toole is the protagonist and narrator of the novel. A native New Yorker, she has red hair and blue eyes, is 29 years old as the story begins, and works at Sotheby’s as an associate specialist. Diana has an art business degree, but she is also a naturally talented artist. She reconnects with this talent by the end of the book. Diana is an only child—her mother was fairly absent throughout Diana’s childhood, being a famous photographer focused on her career. Diana was close to her father, however, who was always loving, supportive, and present.

Diana is ambitious, hardworking, and a meticulous planner, and these traits led her to achieve professional success. As a college student, Diana had set her sights on a job at Sotheby’s, and following an excellent performance as an intern there, she was hired by them after graduating. Diana’s need to plan is not limited to merely her career; it also influences aspects of her personal life, such as her relationship with Finn. To Diana, the comfort and security she finds with Finn comes from the fact that they have matching plans for their careers and their lives together.