There’s a fine line between wanting to protect your children and spying on them. Your children, especially your teenagers want their privacy – they THINK they are entitled to it… So while we as parents reason spying with the urge to protect our children, we often upset them and potentially jeopardize the trusting relationship we have with our kids.

How much spying is too much? There seems to be no right or wrong answer to this… Check out the article that was posted on Huffington Post about this issue:

How much, if ever, should we use technology to spy on our teens? According to Anthony Wolf, clinical psychologist and author most recently of “I’d Listen To My Parents If They’d Just Shut Up,” that question “is one of the most discussed dilemmas in teenage parenting circles.” The italics are Wolf’s.

I’m relieved to know that me and my tribe of post 50 friends with teens are not alone in fretting over this question. Before my son went on Facebook I had one condition: that he friend me so I could keep tabs on him. I’d warned him about the perils of the online world, including the fact that what goes on the Internet has the half-life of plutonium.

What I didn’t tell him, primarily because it didn’t really dawn on me at the time, was that Facebook and all the spokes in the wheel that radiate from this cyber supernova of connectivity (iChat, Google chat, texting, Skype, etc.) would give me extraordinary access to his private world should I choose to avail myself of it.

And the temptation is undeniable. When my son left a long iChat dialogue thread open on my laptop (emphasis on the words “my laptop”), I could not resist reading. I learned about several things he was doing on the sly. They were a little dicey but essentially age-appropriate. I, too, did them when I was his age. In fact, I had far more freedom than he did (another issue altogether). Still, the ability to peer into his world was an enticement to surveil him even more. And in that I’m not alone, either.

But what are the costs of cyber snooping on our kids, assuming they’re not being cyber-stalked or are cyber stalkers, or that nothing truly dangerous is going on? And what do we do with compromising information, whether it has to do with our child or someone else’s child? Does being a parent give us carte blanche to spy or snoop on our kids?

There are no right or wrong answers here, just a sea of subjective opinions as diverse as the parents who assert them. Some parents are control freaks. Others are more laissez-faire. Parenting experts, however, have some pretty clear consensual opinions. Wolf asks: “To what extent do you need to know about everything your child is doing in order to steer them in the right direction or to best protect them from harm? How much do you need to know in order to allow them the freedom and concomitant risk that enables them to navigate future situations better on their own?” It’s almost a rhetorical question.

“Kids that are hell-bent on bad behavior will usually find a way to engage in that behavior,” Wolf continues. And most parents will eventually find out about it in the real world. But “secret snooping has a definite downside. It is dishonest. And if our children find out — which they often do — they will very likely feel betrayed. It says that, in the adult world, being dishonest is okay, provided you have a good enough reason to be. If I could be convinced that sneaky snooping was a significantly useful instrument in a parent’s arsenal for protecting children from significant harm, then I might go along, reluctantly. But I don’t think it is.”

Wendy Mogel, clinical psychologist and author most recently of “The Blessing of a B Minus,” echoes Wolf’s sentiments. In a piece called “The Digital Lives of Your Kids: What Parents Need To Know” Mogel writes of the online world: “Our children’s lives are not like ours were. They’re not free to hang out at the corner drugstore or on the stoop or in a vacant lot. They have little privacy or downtime. They are scrutinized, measured and cloistered. But teenagers need to communicate and connect and express themselves freely. They need privacy and risk. They even need to make a few cheap mistakes before they go off to college.”

The value of the “cheap mistake” — indeed, even the blessings of a B minus, to coin the title of Mogel’s book — is often lost in today’s competitive and fearful parenting zeitgeist. But Mogel and Wolf both have good points. There is no room for what Mogel calls “the experimental floater life” or “a gentle truthiness” — two things we all got away with in our day — when an electronic eye is always peering overhead.

My son can’t get away with a white lie, for example (“Hey mom, can I get on Facebook? I don’t have any homework tonight”) because I can simply go online to Teacherease and instantly check the veracity of that statement. (“That’s not true. You have biology and geometry…”) I can also get real-time snapshots of his grades on every assignment and in every class, making report cards almost redundant.

Like most teens, my son loathes this. I have mixed feelings. On the one hand, I revel in the instant access to his academic progress. On the other hand, I feel like a traffic cop sitting perpetually by the side of the road with radar gun poised. Is there an injustice here, even if the virtues to the parents are evident? And how might this effect my son’s ability to be self-reliant (the subject of Mogel’s first book “The Blessings of a Skinned Knee”)?

A recent New York Times article called “Cracking Teenagers’ Online Codes” explored this terrain in a profile of 34-year-old Danah Boyd, a hip “rock star emissary from the online and offline world of teenagers” who is also a senior researcher at Microsoft and a fellow at the Berman Center for Internet and Society at Harvard. “Children’s ability to roam has basically been destroyed,” Boyd told the Times. “Letting your child out to bike around the neighborhood is seen as terrifying now, even though by all measures, life is safer for kids today.”

Like Mogel, Boyd sees the Internet as the online equivalent of yesterday’s café or coffee shop, where kids should be able to congregate, hang-out, and share their grievances and passions — without parental interference. “Teenagers absolutely care about privacy,” she states. “Teenagers are not some alien population. When we see new technologies, we think they make everything different for young people. But they really don’t. Teenagers are the same as they always were.”

That might be the case, but those “new technologies” certainly make parenting different. The virtual environments in which teens socialize and learn about the real world are also vastly different, posing all sorts of other questions that are as psychological as they are cultural. In fact, if anything seems constant in this new electronic wilderness, it’s that parenting is still as challenging as it is rewarding — and there’s nothing virtual about that.