"The Best Girlfriend You Never Had" is the first story in Pam Houston's 1998 collection of stories, Waltzing the Cat, published by W. W. Norton. Houston won the Willa Award for Contemporary Fiction for the book. As in all of the collection's eleven interlocked stories, Lucy O'Rourke narrates "The Best Girlfriend You Never Had." O'Rourke is a thirty-one-year-old photographer obsessed with finding lasting love. Comprised of a series of anecdotes and reflections in which O'Rourke recounts traumatic childhood episodes with her parents and key events of past relationships—those of her friends and hers—"The Best Girlfriend You Never Had" meanders along rather than charging ahead, while musing on the near-impossibility of finding a suitable partner. In this sense, the story is more of a collage of various encounters and insights that comments on a theme rather than a single story with a unified beginning, middle, and end. O'Rourke introduces characters such as her best friend, Leo, a stand-offish "boyfriend" named Josh, and Lucy's girlfriend, Thea, all of whom appear in other stories in the collection. Houston established her reputation by writing about her attraction to men she knows are inappropriate for her, and this theme also permeates many of these stories. John Updike included the story in the collection Best American Short Stories of the Century in 2000.