1. trying to merge the thoughts, "he's talking dirty" and "he's capable of giving out personal information i think is important" is stupid. They're so far from each other on the spectrum of personality. I don't care how little you know about the kid, THAT IS HOW FOURTEEN YEAR OLDS TALK NOW. You can either get over your dillusions (and i mean this to everyone, not as an indivisual attack on the original poster) that your teenagers have anything but nasty, disgusting, graphic, foul conversations, or you can jerk yourself off to all the monitering software in the world until you really find out exactly what he's talking about..
Parents are so pompous about privacy. Yes, it's your house, and no, they aren't owed any privacy at that age- but use your fucking heads for a moment. You can't shield them from everything in the world, and you can't tell them what to think or how to think.
That is this kid's persona. This is who they're going to be. You can be a positive influence, or you can be an asshole. That's all they understand, and you know it. Use your brain first, before your mouth, and do something to change your situation in a positive way, not just sit there re-reading hours of chat sessions looking for that gold nugget of personal information or whatever you believe is somehow putting you in danger.
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