David Kepesh (Kingsley) is a minor literary celebrity in New York City who shies away from commitment, happy with his casual relationship with a businesswoman (Patricia Clarkson) who is rarely in town. But a date with a stunning grad student named Consuela (Cruz) surprisingly turns into a long-term romance. As their relationship deepens, the professor finds his ego challenged by the girl's enchanting beauty, changing David from a confident Lothario into a jealous boyfriend.