This is my situation
sounds like you need a better haircut... the right hair cut would frame your face better and exposing more of your face (assuming you are a hon) likely exposes all of the features you dislike without actually softening them and probably doesn't look right...
but bad haircuts and unattractive girls aside... i don't like when a chick has her hair up, personal preference, i never think it looks better than well groomed hair that's left down...
Is it really surprising? The kind of stuff in the OP is pretty much romcom tier idealization.
Is it normal for trannies to have such an overly-romantic view of their desired gender? No wonder so many get disillusioned aftet transitioning.