In high school, Chris Brander (Ryan Reynolds) was a shy, overweight teen with a crush on the beautiful Jennifer 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, though, as he attempts to woo Jamie once again, while all the while trying to distract the dizzy pop-diva client (Anna Faris) he has in tow and a rival suitor (Chris Klein). Soon enough, Chris finds that romancing Jamie hasn't gotten any easier in this outrageous comedy of errors!