Viewing love as a contract seems, initially, like mistaking windmills for giants, or a peasant girl for a grand lady. This chapter seeks, like Don Quixote, to convince readers to suspend their practiced views of everyday relationships in order to see them in a new light. What seems crazy at first glance may come to look as good, and sometimes better, than the more conventional view. As a law professor, I usually write about love and contracts by focusing on legal opinions and statutes, and recently I have added real-life stories from books and newspapers, as well as my friends, family, colleagues, and students. But if I am right that love and contracts often complement instead of oppose each other, then my argument that contracts shape the beginning, middle, and demise of love relationships ought to hold true in fiction as well, especially for the jump-off-the-page characters and situations in Don Quixote. Applying this analysis to Don Quixote invites new readings, and may even bring yet more readers to this brilliant text.