@wunderlust89,
Why can't you invite him out for a soda and fries? ask him to join him at a game, invite him to watch your event that he asked about.
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In any case, it seems like he'd like to at least talk with you and you seem to be making it difficult.
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Just use basic courtesies. Say hi, ask him to join you at events etc. Talk to him.
No need to guess.