Honestly I would struggle a bit with this friendship... My DD made friends with a classmate who had some behavioral issues, which I have no problem with but I draw the line when the child doesn't follow the house rules when visiting for play dates. Not a fan of jumping on my furniture, running thru house screaming! I know I have control issues but I would be on edge constantly wondering what they were getting up to! Your DS probably is drawn to his carefree spirit! Maybe just playdates on neutral ground... With a run through of rules before meeting up!