Sounds to me like the guys likes you a long time. Cut him some slack of course, he may come off as obsessed due to the ignorance on your part for not seeing it before; my girlfriend and I are only three years apart: but it sounds like you need to get on board and ask this guy to a movie and tell him your feelings! Trust me; he'll love hearing it; even if he doesn't "like" you back. Which from the description you've given he does. Best of luck!
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