Unceremoniously dumped and branded a loser by his current girlfriend, Nate Cooper (Joel David Moore) recalls his first crush, Cristabel Abbott (Paris Hilton), at the impressionable age of six. Armed with information collected from the Internet by his geeky friend's mom, and convinced she's the only girl for him, Nate decides to move back to L.A. and find Cristabel.

She's still single and stunning, and turning the heads of every man she passes. But there's a reason she's still single; Cristabel is still best friends with the same ugly little girl Nate knew from first grade, June Phigg (Christine Lakin). They live together, they go to yoga together, the only thing they don't do is go on dates together. June has a severe case of the "notties", she's physically unattractive and her personality seems to match. However, Cristabel simply refuses to leave June home alone unless she has a date.

Determined to spend as much time as possible with Cristabel, who has expressed a passionate desire to be with him — if only — Nate sets out to find a boyfriend for June, but guys recoil at the sight of her. Nate concludes June needs a makeover, and she's introduced to a very sexy doctor with all the right moves. However, 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 real hottie at all, and the nottie may be headed for disaster with the doc.