Lane is looking for her "magic man". A man who has all of the attributes that are on her checklist. In the meantime she finally hears her calling when a job opportunity presents itself in the form of Cosmo magazine. After failing to impress the editor they head out of the office when they begin talking men. There Lane (Hillary Duff) has the idea to combine dating and work place. After causing a blackout at her job interview she lands the job in an office to begin her undercover work. After dating several co-workers she happens to spill her drink on a "magic man candidate" Liam. However her boss isn't impress by the direction she tries to take her story and tries to get her to stop dating Liam.