The Troubling Thing About This Movie...
I saw this movie when it first came out, and liked it well enough. But on re-watch a couple of weeks ago I was bothered and put off by a few things.
First, Benny is the heroine. Her character is presented as the chubby, insecure girl who is so spirited and warm and relatable that she gets the handsomest guy in school. But I don't really see her appeal. She's decent and loyal, but her personality doesn't sparkle. She seems kind of needy and self-absorbed. She's a buzzkill. I didn't really get why he would choose her over, say, Eve.
I feel like Jack chose her because he's kind of weak-willed and needy himself, and he wants a mother figure or something. She makes no secret of how much she wants him, so he believes she will love him unconditionally and not make him work for her. Then when she does make him work (or at least wait), he turns to Nan. Granted, she makes it easy, but still.
And then there's the Nan thing. It really bothered me that the one girl who dared to have sex was portrayed as a self-loathing Catholic, backstabber, social climber and manipulator. Whereas the girls who didn't have sex were the sympathetic, deserving ones.
As a result, I kind of found myself sympathizing with Nan. She had a tougher home situation than either Eve or Benny. Her father is boorish, her mother beaten down. She wants to escape that trap, and she uses her best weapon, which is her beauty.
The whole message of the movie bugged me. The characters were not nuanced enough, and there were no gray areas. Benny was a good girl who deserved Jack, Jack fell from grace and now has to prove himself utterly devoted to her in order to get her back (never mind his needs, it was all about Benny), and Nan was the whore and the villain.