Why does my boyfriend keep taunting me about other girls and smiling when he knows it upsets me? How do I get it to stop?

Anonymous
Ever since my boyfriend of 5 years and I started doing long distance over half a year ago (countries apart), he seems to enjoy taunting me. He jokes about getting close to other girls and girls hitting on him, and I can hear him smiling, waiting for my reaction.

Also, he recently said that a girl who had broken up with her boyfriend was "dramatic" and "weak" for saying that she [was so upset that] it felt as if someone close to her had died. I told him that he shouldn't judge since he has never been through a break up. He praised another girl in comparison who ended her relationship and said "meh", saying "that's the spirit!" So I asked him, if we broke up, would you just think "meh" and not feel anything? Because he was crying the day he left our house to move overseas. He said he was sad but that ended after 5 minutes when he realized his bright future ahead of him.

Right after that he talked about me coming to visit him and watch him at his conference so that I can be his "trophy wife". I understand that these are just stupid jokes but the way he grins at me, waiting for my response, as I feel upset I find immature. I've told him so many times that I don't like it when he does this and he apologizes, yet he keeps doing it. His ego has also been inflating a lot since moving to go to a prestigious uni and I don't like the way he talks about other people that he perceives are "below" him, claiming that they are "rotting away". I am not recognizing him so much anymore. What do I do?
Why does my boyfriend keep taunting me about other girls and smiling when he knows it upsets me? How do I get it to stop?
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