First of all my boyfriend and I (not to be rude) are two very attractive people. We are both 23, work out every day, and my mom says we look like a Barbie and Ken except not idiots, haha. But anyway through most of my childhood I was very awkward and kind of ugly. I grew into myself but I still have the heart of an "ugly girl". My boyfriend doesn't help..he's been gorgeous his whole life and if I look bad one day he'll say "What did you do with your makeup? You're wearing too much/you're wearing it wrong, you look weird today." He doesn't understand why that would upset me. Also when I tell him I'm thinking of getting surgery for my face, he always tells me "Okay then go ahead if it makes you feel better," instead of saying "no, you're perfect the way you are."
The weird thing is, he thinks I'm prettier than every girl he knows, and he tells me this. He says it's really important to HIM that I think I'm gorgeous, but how can I think that when he always criticizes me? I feel like we are always arguing about this, and he just says that if a person doesn't like an aspect of themselves they should change it, whereas I think unless its a deformity, people should learn to love themselves regardless. So why does he do this? Why does he tell me I'm the most gorgeous woman he's ever seen, with full sincerity, and then tell me what's wrong with me? And how can I stop starting fights about this?
He's never been known to sugar coat anything...if he was saying this to make me feel better, then he wouldn't say the mean things to begin with.
I'm not angry because I know he isn't trying to be mean, but it does bother me.
You can easily just blow off what he's saying or tease him about his fastidiousness about you looking your best. You can't change his attitude, but you can change the way you react to it. Maybe if you didn't react so strongly to his helpful suggestions, he would take the hint and lay off. Obviously, since you've fought about it, it's been previously discussed - so change tactics and laugh it off or ignore it.
As for why he behaves that way - it's because you're insecure and it sounds like you are constantly looking for his approval on your looks. I guess he now feels like it's his duty to help you out. Your insecurity is understandable, since you've described yourself as a previous ugly duckling, but it sounds like you're having problems getting over it. Maybe if you stopped emphasizing the importance of looking good, he will too.
If his comments upset you let him know. A closed mouth doesn't get fed honey. I would be offended by a guy saying that to me too. Unless you look really tore up that day he shouldnt say that you wear your makeup wrong.