My boyfriend makes me feel bad about myself

Anonymous
My boyfriend is 19 and I'm 22. He has everything about him together except that he can be immature at times and say stupid things. He will make comments about other girls' boobs and when we first met he made comments about my boob size. I am quite small and he used to make little digs at me like when we were out shopping, holding up large bras on me and saying "one day". I finally said I will not get a boob job ever, and he said, "you look great how you are I don't want you to change I'm sorry I never meant to hurt you by saying that." But how can he not know that these comments make me feel ugly? I never make comments about his outer appearance. He says I look pretty all the time and when I'm naked he said one time "how did I get so lucky?", but then he goes and makes these comments about his older brother's girlfriend and how she has bigger boobs than the girlfriend before her (which tells me that he was checking her out.) It's just all chest size to him and it's hurting me. It is clear that he is very self conscious but how do I feel better about myself? Does he really mean what he says or is this some kind of mind game he's playing to feel better about himself?
My boyfriend makes me feel bad about myself
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