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Originally Posted by Ramrod
I would allow it but I would also seek out some way to 'check up' on the conversations from time to time (keystroke logger or something) to see if things were taking any 'undesirable' turns. I know it's deceitful, sneaky and underhand but when it comes to protecting my kids I have no shame 
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You can get MSN to save conservations into a folder of your choice, so just get msn to save it into a folder located on your password.
Again i think that the fact the child is talking to a adult on the internet would be of far greater concern to most parents than if they are gay or not.