Lexy Gold (Lindsay Lohan) lives amongst the wealthy and elite of Manhattan, New York. Clad in Prada, she prides herself on her ability to get the scoop and serve it up in her school newspaper's advice column. She competes for status on the newspaper with middle-class Jack Downey (Bug Hall), the editor. When an article and photograph Lexy has taken of her teacher, Mr. Orlando Walker (Ian Gomez), is published in the city's daily paper, he goes missing and his car is found in the East River. With help from Lexy's best friend Jen (Brenda Song) and one of her schoolmates Gabe (Ali Mukaddam), Lexy and Jack set out to solve the mystery behind the disappearance.