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I don't mean to be glib or condescending, but the kid took a chance and made a stab, and you dumped on his face. Not too difficult to diagnose here, it's pretty obvious why he's upset and uncomfortable.
To "bridge the gab" you'll have to start to address his discomfort, and redraw your boundaries, as apparently they're shorter for you than they are for him. Basically, he had set his hopes (and put himself on the line) for one particular outcome, and you 'laughed at it' then flat rejected it. Those feelings will have to be addressed. It seems like you two prob have some communication issues to start, which will make it hard, but hey anything's possible.
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