This updated Cinderella (Hilary Duff) is named Sam, wears pink high tops, and spends her off-hours exchanging anonymous emails with her Prince Charming-to-be, high school quarterback Austin Ames (Chad Michael Murray). Raised by her amenable, hardworking dad Hal (Whip Hubley) to appreciate tomboyish pleasures rather than femme fashions, she’s understandably devastated when, first, he, marries wicked, botox-injected Fiona (Jennifer Coolidge), and second, dies in a Los Angeles earthquake.
You might imagine these are terrible trials, but, this being a romantic teen comedy, the trauma is fleeting. Or rather, it leads directly to Sam’s present day misery, living in Fiona’s attic and playing always-on-call servant to her and daughters Brianna (Madeline Zima) and Gabriella (Andrea Avery). The stepsisters take water ballet classes for an instructor who visibly loathes their gaucherie but, like everyone in this film’s L.A., lusts after Fiona’s money, and so puts up with all kinds of humiliation. This “everyone” includes Sam, whose moral compass is somewhat skewed by her desperation to leave home (such as it is); a high school senior, she’s applied to Princeton, and presumes Fiona will pay tuition — as long as Sam performs her scullery maid duties with a smile.
While she has enough to do at home, Sam also works for Fiona at the diner that Hal once loved and tended; now renamed “Fiona’s” and done up in the tackiest of décor (a porcelain Elvis guitar clock), the place still does decent business (and keeps Fiona and her daughters in expensive terrible clothes. Before and after school (where she’s a straight-A student, of course), Sam waits tables (which entails roller skating and nametag-wearing), scrubs floors, and does dishes, encouraged to keep on by her dad’s loyal-after-death employees — Rhonda (Regina King), Bobby (Paul Rodriguez), and Eleanor (Mary Pat Gleason) — the working class “others” whose approval makes Sam look gallant and admirable even when she’s behaving as selfishly and childishly as anyone her age might.
Sam is relentlessly harassed by whiny Brianna and Gabriella (someone calls them “wannabe Olsen twins”), as well as her mean classmates, including standard issue bitch-diva/head cheerleader Shelby (Julie Gonzalo), who happens to be dating (or so she insists) Austin. Since Sam’s support system at the diner (“You got a whole family behind you!”) can’t follow her to school, she has a best friend there too, a nerdly boy named Carter (Dan Byrd), who has an inexplicable but convenient crush on Shelby. (His primary function appears to be providing his mother’s car, to transport Sam to the Big Dance.)
Since the conclusion is foregone — Sam and Austin will hook up, her dreams will come true — Mark Rosman’s feeble film wrangles slight innovation out of its email gimmick (call it: You’ve Got Mail meets Ella Enchanted meets Confessions of a Teenage Drama Queen), though Austin is so terribly slow on the uptake that even when he meets his dream girl in person, at the school’s Halloween dance, he doesn’t recognize her. Yes, she has a dainty mask over her eyes, to go with the wedding dress that Rhonda has lent her — and don’t even get me started on the aggravation of this plot point, that Rhonda (call her: Fairy Godmother) happens to have a wedding dress, boxed and waiting and perfectly fitting Sam, and Rhonda apparently has no life outside the diner and Sam — but still! He sees her at the diner and/or school every day (he’s part of the crowd that taunts her at work; they call her “Diner Girl,” so imaginatively).
While it’s completely unclear why Austin is the boy of Sam’s dreams (his writing skills hardly seem extraordinary), her appeal for him is also vague. Apparently, on email, she encourages him to “be himself,” that is, not the football star who’s destined to take over his dad’s car dealership, but a poet. You heard me. A poet. And he imagines her as “not just some chick. She was real, with more on her mind than what she’s gonna wear or how much weight she’s gonna lose.” Or so he tells his idiot best friends.
Once Austin does learn Sam’s identity — via a horrifically mean skit performed by Shelby and the stepsisters, in front of the entire class at a pep rally (why are high school movies so extremely predictable? Is there no one in the business today who’s seen Heathers?) — he must make a decision: stand by his dream girl or play by dad’s rules. Gee whiz.
Worse, Sam waits on Austin’s decision. There’s a roundabout bit of business just before the Big Game, when she decides she’s lost everything and so she can march into the boys’ locker room to tell him off, but really, her happiness is contingent on him making the right choice, and on Fiona getting what she deserves. Derivative by definition, this shoulda-been girl-power movie is only another tween fantasy, in which the girl gets the boy.