Useless personal anecdote: My mother never tried to monitor or limit my online freedom. By the time we got internet into the home, I was far more savvy in such things than she is to this day, and my knowledge increased rapidly when given access to the wellspring of information that is the online world. Indeed, even out in RL (as the kids are calling it these days) I didn't have a lot of restrictions, and was pretty much free to come and go as I pleased within reasonable limits from about 14 on, so long as she knew where I was.
I like to think I turned out more or less okay, because I'd been raised in an environment valuing respect and responsibility.
Eventually you have to trust your kids to make the right decisions for themselves. The teenage years are when the limits should be expanded, and the pace at which that should occur is highly context-sensitive.
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I wake up in the morning more tired than before I slept
I get through cryin' and I'm sadder than before I wept
I get through thinkin' now, and the thoughts have left my head
I get through speakin' and I can't remember, not a word that I said
- Ben Harper, Show Me A Little Shame
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