Nate Cooper (Moore) cannot sustain a relationship with a woman, due to continuing to be in love with his childhood crush Cristabel Abbott (Hilton). He sets out for the beaches of California to pursue her, learning from his best friend Arno (Wilson) that she has grown to be the hottest woman in California. Nate also learns to his horror that Cristabel won't enter a romantic relationship until her best friend, June Phigg (Christine Lakin) has. And June, as it happens, is the ugliest woman in California. Not to be deterred, Nate sets about landing June a date.
His efforts prove in vain, until Cristabel meets attractive dentist Johann (Johann Urb) who, pursuing Cristabel on the sidelines to Nate's chagrin, offers June cosmetic surgery. June accepts. Up until now, Nate has been disgusted by June as has every other man in the movie, but once she's got the surgery thus rendering her beautiful Nate falls in love with her instead.
This film provides examples of:
- Author Avatar: Cristabel is basically Paris Hilton playing Paris Hilton.
- Chick Flick: Matches the standard formula of one.
- "Friends" Rent Control: Cristabel works for a charity organisation, and June works at a zoo. Apparently, they earn enough to afford beachfront property in LA.
- Genre Shift: At about the one-hour mark, the film stops being gross-out comedy and starts being a standard Chick Flick.
- Gonk: June.
- The Grotesque: June has shades of this
- Line-of-Sight Name: Nate and Cristabel are at a picnic and she asks him the name of the date he has supposedly got for June. He comes up with Cole Slawsen.
- Meaningful Echo:
- The "out of breath moment."
- That Junes goes on the boardwalk at night after everyone's left.
- Mr. Fanservice: Johann.
- Never Trust a Trailer: The UK trailers for the film called it "The Number One Film" - adding in small print that it was number 1 film in the IMDB Bottom 100 at the time of release.
- The Noun and the Noun: Which also invents a new word to get the rhyme.
- Secret Test of Character: Cristabell pulls this on Nate.
- Setting Update: Shakespeare's The Taming of the Shrew IN BEVERLY HILLS! With a hint of Pygmalion, only without the dialect changes.
- Stalker with a Crush: Nate. Lampshaded by Cristabel.Cristabel: You stalked me.Nate: "Stalked"... is a big word...
- Wedlock Block: As a The Taming of the Shrew variant, this is natural, though it is a self-imposed one.