Harper Stewart is a writer living in Chicago with his beautiful and free-spirited girlfriend, Robin. The movie opens with Harper returning home from a day of meetings to inform Robin that his semi-autobiographical debut novel, “Unfinished Business,” has been selected by Oprah’s Book Club and will be fast-tracked for publication. They celebrate by lounging in a tub, but even though they have been dating for two years and all appears well in their relationship, Harper balks at the mention of marriage. Robin is hurt by his reaction and assumes it is because Harper still has feelings for the college girlfriend he wrote about in his novel. Despite this, Robin agrees to attend Harper’s best friend’s wedding in New York.