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It's possible that he didn't know that he was hurting your feelings. I listen to the way the teenage boys in my classes rank on each other, and I'm amazed at how this serves as a form of bonding ritual for many of them. It may be that he's just treating you like one of his guy friends, taking shots as a way of being harmlessly entertaining, without realizing that it's possible to cause real hurt.
Or it could be that he was just being a jerk. The tone of the conversation is important in understanding the difference.
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