We lock eyes for months- but WHY?

there's a guy who I see around regularly at the same place. In the very begining he would smile. But i was too shy to smile back and he eventually stopped. With time I noticed him talking about me, but i couldnt tell if good or bad. I would also make A LOT of eye contact with him. From a distance, he will hold it, and I am the one to get nervous and look away. He knows my friends, he will say hi to them even though he doesn't know them well, but nothing to me. Not to mention he pays attention to who im with and what we do (their words not mine). When I randomly talked to him once he turned red. And i didn't really get another chance to say something.
Either way, now I know some of his friends. I hang out with them and we talk some. When I was talking to his friend he came in and said hello to him but seems uncomfortable with staying. His friend didn't want to leave and he had to awkwardly sit and stay a bit, he listened to me talk at first but then once I made eye contact with him he stopped looking and then went fidgeting on his phone. Why is it so difficult to understand him? Im trying to approach and make it easy and its only getting harder.
We lock eyes for months- but WHY?
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