At the beginning of the the film, Andie Anderson (played by Kate Hudson) comforts her friend, Michelle, who has been dumped because she was too clingy, needy, weird, etc. Michelle (played by Katheryn Hahn) says that the beautiful Andie wouldn't get dumped for making the same mistakes. Andie sets out to prove her wrong. Enter Ben, the poor victim, who gets treated to 10 days of alternate personality Andie. And he falls in love with her anyway. So essentially, Michelle was right.
Not really, since he does make it clear when he first breaks up with her that he was attracted to the confident, ambitious journalist he met the first night, not her clingy act.
Ben: "That's what I'm talking about. Where's the sexy, cool, fun, smart, beautiful Andie that I knew? The one that wanted to be a serious journalist? You're up, you're down, you're here, you're there, you're like a frickin' one woman circus."
Sometime in the middle of the film (after a few days of Andie and Ben dating), Andie brings in a photo album depicting poorly photoshopped images of their (Andie's and Ben's) "future" wedding, first child, first family vacation, and two children along the way. Soon after, Ben's mother calls for Andie and they speak on familiar terms and talk about the album. What I don't understand is how Andie, having known Ben for a handful of days, if that, can talk to his mother on such familiar terms without meeting her and also having his mother's approval to compile that album in such a short amount of time of knowing each other.
Maybe that's why he falls so hard for Andie; his mom is a psycho, and Andie reminds him of her.
What bugs me about this film (something I found particularly hard to explain) is that their roles are not symmetrical. While he has to make her fall in love (in order words, a constant growth), she has to be attractive at first and then make him dump her (up and then down).
The problem seems to be that you're expecting actual egalitarianism in a modern Rom Com.