Nate Cooper (Joel Moore
) has been smitten with Cristabel Abbott (Paris Hilton
) since he first laid eyes on her at the impressionable age of six. In the intervening years, there have been other women in Nate's life, but none who could measure up to Cristabel.
Convinced Cristabel is the only girl for him, Nate decides to move back to L.A. and track her down. The good news: she's still single and stunning. The bad news: there's a reason she's still single. Cristabel's still best friends with the same ugly little girl from first grade, June Phigg. The two are inseparable. They live together. They go to yoga together. They would even go on double dates together...if only June could get a date. And Cristabel simply refuses to leave dear June home alone.
Determined to spend as much time as possible with Cristabel, Nate sets out to find a boyfriend for June. But guys all flee at the sight of her, and it hits him: June needs a makeover. As Nate and June become friends and she emerges from her cocoon, Nate slowly realizes that the girl of his dreams may not be the hottie at all...