We still like our 15 1/2 year old home before dark, so I would also have said no to walking even a few blocks in the dark. Going next door in the dark is a bit different though so I probably would have allowed that. If I was ok with him going to the girl's house (which it sounds like you weren't due to particular reasons) I would drive him rather than let him walk in the dark. Up until recently we had Interguard on his computer which monitored his internet activity including messages and he was aware of it.