I don't think monitoring software is an invasion of privacy.. but then again, I don't think that 14 year olds are entitled to all that much privacy... Keep a diary if they want privacy... but once they hit the big bad world outside (even online) then it's a parent's responsibility to know what that child is doing, where they are going etc.
Putting the monitoring software on behind your wife's back, however, is wrong. Instead of monitoring software, what about using parental controls in windows and giving the kid his own login to the computer? BUt that needs to be discussed with your wife as well...
I get the feeling that maybe your wife is trying to make up for lost time with her son. That she's been a little detached from his life til now and she wants him to like her... (COuld be wrong though) and she doesnt want to rock the boat with him. Janey's right with the be a friend to your child... She's his parent not his buddy.. He's gonna need some rules and some boundries... and you and your wife have to be on the same page (otherwise if he's a devious child, he can and will play the two of you against each other)
Good luck...
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