He probably does have an obsession with breasts. And his comments about you and his brother's girlfriends are immature and completely inappropriate. But from what you say, it's not clear that he has any idea how bad this makes you feel. Have you explicitly told him that these comments make you bad about yourself? If you have and it continues, this does not speak well of him. If you haven't, don't assume that he will connect the dots on his own. He probably doesn't know that it really hurts you. At least, it's worth giving him the benefit of the doubt.
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It sounds like he does like bigger breasts in women, but he also appreciates the way you look as well. I wouldn't take it personally, I don't think he's playing mind games I think that is how he feels but that doesn't mean that he isn't into you or your relationship just because you're a bit smaller up top. If he always jokes about that stuff, you should tell him that you're insecure about your boob size and he should stop if he cares about you.
I think that you really need to tell him that if you respect him and don't compare him then he needs to give you the same kind of treatment. He might be insecure because of your age difference or have low self steem.
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I think he just feels comfortable opening up to you. He is so comfortable that he lets his guard down completely and tells you what ever is on his mind. I am in a steady relationship and I am always doing this with my girlfriend. Jst the other way round. How she will never look good in some clothes because of her larger boobs. And she also joins in sometimes. It's kind of fun discussing boobs with your gf.
It seems that he's quite a jerk now.
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