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Been through this with my own. First of all, as mal already stated, 14 year olds are not entitled to all that much privacy. You, as the parent, or in your case...the parental figure, not only have a right to know who, what, when and where he is up to...you have a responsibility to know.
Hey...kids are kids. We've all been there, right? Unless he's into something harmful, and not just over your comfort level, then try to keep a fairly open mind about it. Your wife wants to trust the kid, and that's probably as it should be. Give the kid, and your wife, some latitude. Give him that trust. Until, that is, he's caught abusing it. Then it's time to break out the monitoring software, and the chat logs, etc, etc. Give him a hands on history lesson in what life may have been like in the Soviet Union, under Josef Stalin. Then, gradually...let up, and see if he's picked up on the lesson.
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"I distrust those people who know so well what God wants them to do because I notice it always coincides with their own desires." - Susan B. Anthony
"Hedonism with rules isn't hedonism at all, it's the Republican party." - JumpinJesus
It is indisputable that true beauty lies within...but a nice rack sure doesn't hurt.
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