I never really liked the lyrics to this one, and being prompted to think about it, I know why.
It's a song from the perspective of an insecure, jealous girl, whose reliability as a narrator is unknown. She saw this guy wanting another girl in high school and him being rejected by her for whatever reason, while narrator girl was passed over. Any motivations she assigns are pure projection, or possibly, his opinions, because we don't know if she ever knew ballet girl and may be basing everything on her boyfriend's opinion. Oh yeah, he says, she totally rejected me because she's a bitch, not because of anything wrong with me! Considering they are both creepy and petty enough to be writing a song about someone in high school, I give them no benefit of doubt.
Then there's the real nasty part. Five years later--so, what, they are at most 23 now?--ballet girl is a mother. So there was someone else she liked and clearly got involved with besides skater boy. This is used dismissively as some kind of contemptible fate; also "she's alone" because she's the stay at home taking care of a child, or she was abandoned, possibly (shit, maybe the father died). By comparison, because they are rich and famous, they "win". That's quite a horrid judgement, displaying an awful mentality. Again, they assume they know everything ballet girl wants and thinks.
That's the final point. Narrator girl claims she's better because she could see the "soul inside" beneath the rough exterior. OK, nice message, and assuming the narrator is right about ballet girl's inner feelings and her friends, which we don't know, maybe don't let your bitchy friends dissuade you from following your heart. But what's the sole criterion showing he is a good soul? That he's rich and famous now. In reality, that means nothing about how good or bad you are; it's basically irrelevant. But if you are going to generalise on that quality, it would far more likely mean you're a piece of shit.
So the end message is the old nasty, ubiquitous one that being rich and famous is all that matters, makes you a good person, and means you win, so you can rub it in the faces of anyone who didn't do what you wanted. You'll regret not dating someone who later becomes rich and famous because you missed out on the wealth and fame!
Fuck off.