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Why is my friend trying to make this girl jealous and miserable?

This he liked this girl— although the was in a long-term relationship with his current live-in girlfriend— and she rejected him when he asked her out. Now he does everything that he can to make her jealous and irritate her until she is on the verge of tears. He’ll brag about what he bought his girlfriend or text her to ask for date ideas. He’ll make fun of her for being single. He constantly go out of his way to tell her that he “only sees her as a little sister”. He’ll purposely bring his girlfriend to events that he knows she’ll be at.

Yet, now that she wants nothing to do with him and is dating other guys, he desperately tries to get her attention and dig up information on her dating life. He keeps asking mutual friends (like myself) what she is up to. He gets mad that she’ll talk to other mutual guy friends but not him. She’s told him that she’d rather not talk to him, but he keeps trying to find reasons to talk to her.

Why does he try to make her jealous? As a friend to both of them, it’s hard to watch.
Why is my friend trying to make this girl jealous and miserable?
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