The Hottie & The Nottie (2008)

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Nate Cooper (Joel David Moore) has been smitten with Cristabel Abbott (Paris Hilton) since he was six years old. But before he could try and snuggle up to her at nap time, his family moved away. Now, years later, he moves to Los Angeles to find his long lost love. The good news: Cristabel is still single and stunning. The bad news: Cristabel is still best friends with June Phigg (Christine Lakin), the ugly girl he remembers from first grade. The catch: he has to find a boyfriend for June before he can make his move. Using every trick in the book to find June a boyfriend, Nate discovers that romance comes in many shapes and sizes - and that true love can strike when you least expect it.