He loves her. She loves him not.
In high school, Chris Brander (Ryan Reynolds) was a shy, overweight teen with a crush on the beautiful Jamie Palamino (Amy Smart). Unfortunately, Jamie thought of the good-natured Chris as "just a friend." Fast forward ten years, Chris is a suave, fit and successful music executive visiting home and looking for a little payback. Love has other plans for him, as he attempts to woo Jamie, all the while trying to distract the ditzy, pop-diva client (Anna Faris) he has in tow and a rival suitor (Chris Klein). Soon enough, Chris finds that romancing Jamie has not gotten any easier in his outrageous comedy of errors!