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Well just try, maybe your friends just thought he was homeless.
holy shit...how desperate are you? you accepted a date with someone you don't know at all? that's just crazy!!
Why does it matter where he does or doesn't live? Some people fall on hard times. It doesnt mean you shouldn't give him a shot
Keywords
Um, desperate much? If they look homeless, I'd be cautious just to talk to them. This is a whole new level of... awkward. Random guys you meet at bus stops that ask you on dates... Just... No.
umm, didn't he even look homeless? hahah