Joanne, a fashion photographer, helps her friend, Lane Daniels (Hilary Duff), an aspiring writer, get in to see Kate White, primary editor at Cosmopolitan Magazine, to pitch a story idea - which doesn't go well. On the way out the door, Kate and Lane discuss how hard it is to find a good man, which leads to Kate assigning Lane the task of joining the business world to find a man amongst all those eligible 'downtown' bachelors, and writing an article about that. She is to go under-cover and look for her 'magic man' (one for whom she has a lengthy checklist of desirable attributes, as opposed to her friend Joanne's checklist which consists of: 1- breathing, and 2- cute). With a fraudulent résumé, Lane bluffs, bumbles, and sabotages her way into getting an administrative assistant position in the Corporate Strategic Planning department of a major investment firm. She is to work for Tom Rinehart (Michael McMillian), Managing Director, who is a bit of a quirky 'stick in the mud' when it comes to personal 'risk-taking'.