A little history with this guy in that he is a player / flirt and acts like he is not. So in the past, I responded to his flirting as though it was interest and he completely rejected me as though he had no idea what I was talking about. We worked another season together where he was a complete jerk to me (he was my boss) and he was nice after the season ended. For the 2 months afterwards, he was constantly giving me crap / teasing me in our class together, which I did not respond to. Class is over and I have taken the approach of just keeping to myself and focus on my stuff while were at work (I'll respond to him to be polite, but try to keep it brief). When we are out with our group of friends, he interrupts my conversation with our other female friend (and then excludes me from the conversation), or makes almost mean comments about me (for example: "oh, she got my spoon dirty from her coffee stuff" or "her face always looks mean"), he even called me the "ice queen" in front of them. But yet at times, he will show concern for my well being (almost nosy), stand up to our friend that we both dislike when she makes comments towards me, and he will bring up stuff he remembers about my family / or that I've said. He tries to start conversations (usually about himself: oh I started working out or I really didn't enjoy reading that article for my meeting, etc.) He has a girl that he has been "seeing" this entire time and with his track record I have just been trying to stay away from him (because I get dirty looks from all of his little girls). At one point I really thought that he liked me and I was embarrassed when I misread him, and I just always felt like an ego boost for him. So why is he being a jerk so much? Is he mad that he can't use me as an ego boost anymore? And why won't he just leave me alone? I can tell that my opinion of him bothers him, but it's come to the point that I no longer go out with our group of friends and I keep to myself at work.