He could either be an idiot.... Is he an idiot? Or he is hiding feelings and is afraid to face you. If he didn't care he wouldn't be asking about you at all.
When I was young a man loved me and I turned down his proposition to be his woman because I loved him but like a best friend not as an intimate partner. It hurt him deeply and I asked for forgiveness 3 separate times but I could see the bitterness in his face and he puffed his cigarette. He said he forgave me but his action said differently. We quit talking and my mom being a waitress at the time switched jobs a lot and he would go to lunch with lady friends at work and find my mom and on a weekly basis ask her how I was. After 10 years of silence he finds me and he was so sorry for what he did and he's my best friend again and then some. So I am sensing here that this man you speak of has hidden feelings.