Nate Cooper (Joel David Moore) has been smitten with Cristabel Abbott (Paris Hilton) since he first laid eyes on her at the impressionable age of six. But before he could try and snuggle up to her at nap time, or maybe send her a valentine, his family moved away. In the intervening years there have been other women in Nate's life, but none who could measure up to Cristabel. Convinced she's 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 Nate remembers from first grade, June Phigg (Christine Lakin). 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 even when he pays them, guys all flee at the sight of her. And then it hits him: June needs a makeover. But as Nate and June become friends and she emerges from her cocoon, Nate slowly realizes that the girl of his dreams isn't the hottie at all. It's the nottie -- who turns out to be something of a hottie herself.