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One of the main rules in any professional relationship is that you don't become friends if you want things to stay copacetic in the work place. Issues get muddy and then things get misconstrued and boundaries get crossed. I know its your guy's business and part of the attraction of that is that you don't have to be in a stuffy office, with a stuffy office environment. But there is a reason why that cliche exists. At this point its probably impossible to switch gears but if there is ever another intern... its worth a shot.
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