Hallie is the female romantic lead of the novel, one of the two main protagonists. She is in her mid-twenties, having graduated from college eight years prior. She grew up in the town of Omaha with her parents and a younger sister, Lillie. In school, Lillie was perceived as the messy sister while Hallie was the responsible one who had it together. Hallie has a full-time job as a tax accountant and enjoys her work, but when the story opens, her life has become something of a shambles. It’s been a year since she broke up with the man she loved, Ben. Ben’s telling Hallie he loved the idea of her more than he loved her shook her confidence, and she gave herself a period to recover, calling this the winter of her twenties. In this winter she’s taken on two part-time jobs, one as a bartender and the second at a jewelry store, and shares an apartment with Ruthie, the eccentric friend of a coworker, while she saves up to afford a place of her own.

Hallie is not the type to have one-night stands, and doing so with Jack—a man whose last name she doesn’t even know—comes to represent the epitome of irresponsibility, her rock bottom.