Why is he trying to purposely make me jealous?

Either he really has a personal hate against you. Or more PROBABLY he doesn't have social skills which enable him to understand others. Unable to admit to himself that he likes you - I see this most often. It's like in pre-school where you're young and can't deal with liking a girl so you be mean to her. He just doesn't know how to get you and so the other option is to run away and try to completely avoid having to face the fear of liking you. This is complete normal behavior for a under 18. You youngsters shouldn't think you know how to deal with your own emotions and social problems. It's something you'll naturally learn and develop as you get older.
You yourself should toughen up your act and not let immature behavior upset you. And why are you even affected unless you like him back?
I dated a guy 10 years older than me and even has more experiences in terms of dating. he used to even have a reputation in the past.
but it nevertheless makes him anything mature.
I have talked to him I dont like him talking about women in that particular way, got me crying even to the point.. he destroyed my self esteem. and he said he loved making me jealous because it makes him secure that i am with him. Guys do it to assure themselves, yes, that pathetic.
My only advice is to you is to get out. You don't need somebody disrespecting you in order to give themselves a fresh buzz
If someone is purposely trying to make you jealous, it just goes to show how immature they are. I wouldn`t waste my time on them if I were you.
He does it becuase he knows he can get a reaction out of you and the fact that you said it makes you upset and cry just gives him a buzz, I guess.
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