Coming-of-age romantic comedy loosely based on the series of short stories by Melissa Banks. Brett Eisenberg (Sarah Michelle Gellar) is a young woman attempting to work her way up New York City's publishing ladder. Brett attends a book signing, hoping to meet influential publishing giant Archie Knox (Alec Baldwin). No sooner do they trade glances than Archie is wooing Brett with extravagant dates, expensive gifts, and career assistance. The relationship is a storybook romance from the start, but slowly becomes complicated due to the couple's age difference and Archie's drink problem.