If you could see every email, every chat, every internet search your teenager does on his laptop late at night would you want to? Because if you want to, you can.

I know this because one day at lunch in a restaurant I ran into a friend, whom I’ll call Mrs Orwell, and she told me that she had started monitoring her daughter’s computer by installing spyware. Before I go any further I should say that Mrs Orwell is in no way the drab or crazy person you might imagine from this particular vignette. Instead she is quite glamorous and sensible and fun; she is busy with her own life, and does not seem unduly or excessively involved with her children. Which is why when she told me that she was secretly monitoring her daughter’s every move on the internet, I was intrigued. If anyone else had told me the same thing, I would have thought, well, she’s nuts or dangerously bored.

The reason Mrs Orwell turned to spyware is that her 15-year-old has a very serious, brooding boyfriend. She had come across some evidence (in the real world: a diary entry left open on a desk) that the boyfriend was dangerously or theatrically self-destructive, and so she was worried about her daughter.

After a certain amount of inner turmoil, Mrs Orwell installed a program that a friend introduced her to, called eBlaster, which gives her a written report of every keystroke made on her daughter’s computer.

The eBlaster website gives the following example of its omniscience: “4pm Your daughter comes home from school and goes online. 4:15pm She receives an email from a guy named Tom. 4:16pm within seconds eBlaster sends you an EXACT COPY of this email to your work email address. 4:30pm Your daughter replies to the email from Tom. 4:31pm within seconds eBlaster sends you an EXACT COPY of her reply.”

The question of whether you need an “exact copy” of Tom’s email “within seconds” and what you might do with it is left to the imagination.

In recent years SpectorSoft, the company that markets eBlaster, has seen robust sales as anxieties over teenagers rise. A spokesperson from the company says that it objects to the term “spyware”, which she calls “old school”. She says, “I mean, do they also have dial-up modems?”

Mrs Orwell tells me that she only scans the voluminous reports. She doesn’t read them word for word. For one thing, she would die of boredom. She has learnt that her daughter is not sleeping with her boyfriend. She has not uncovered any sign of drugs. “There are a lot of private conversations that she has with her boyfriend that I would rather not have seen,” she says. “And I have to say the sex chat skeeves me out.” But most of what she reviews is innocuous, bland.

She does like to know what her daughter is up to, who her friends are, what they are like, whose parents are pretty absent. (When she says this, I think guiltily to myself that I will probably be one of those pretty absent parents.) Through all the chats, she gets a better sense of the characters in her daughter’s life than other parents get from sketchy answers and fleeting glimpses of a friend on her way out of the door.

Most sane people will interrupt here: “But you should be talking to your child!” Of course you should, but as anyone who has ever been, or talked to, a glowering 16-year-old knows, sometimes talking doesn’t work. Not to mention the fact that recreationally lying to one’s parents at that age is not exactly unheard of, or exotic, or even a sign of particularly bad character.

Even for those of us who have not yet had the misfortune of having teenagers, it is very easy to imagine the scenario of temptation: an opaquely troubled 15-year-old, a helpless and increasingly anxious parent, several well-intentioned but totally thwarted attempts at actual conversation, laconic or cryptic utterances, moody poems or doodles examined like hieroglyphics, a bad influence who skulks into a room.

Still, should the temptation be resisted? When I wonder out loud if kids should have a little time outside parental scrutiny to gain some measure of independence, Mrs Orwell makes the clever argument that what they really need is the “illusion of independence”. That is, they need to think they are on their own acting responsibly, when in reality they are not yet even remotely on their own. (Here one thinks of the relatively benign scenario of parents shadowing a child walking to school on their own for the first few times. The child thinks she is walking by herself but the parents are watching from a safe distance, just for a while, to make sure everything is OK.)

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This seems like a thought-provoking point but I am not so sure that the shadowing is as benign in later life. One could argue the value of privacy for teenagers is the space to make mistakes, to do stupid things, to regret decisions, to take risks, to venture out, to learn. Naturally we want to protect our children for as long as possible, and sometimes by whatever shady means possible, but what if in protecting them we are also crippling them? What if navigating the internet is the (granted often mindless) work of those years, what if facing the nastiness of other kids, or putting vampy photographs on Instagram, or doing crazy internet searches is part of how you learn independence or forge a strong, separate identity? What if someone trusting you to be on your own is more valuable than all the monitored chats, all the pillowy protection of parental oversight?

The beautiful Mrs Orwell remembers sneaking out at night and going to nightclubs when she was close to her daughter’s age. Her parents gave her rigid curfews and she rebelled. But the idea of her children engaging in the wildness she did horrifies her, which is, I think, a pretty common feeling. I say, “Well, we survived.” She says, “Only by chance.”

The city is by any external standard safer than when Mrs Orwell was slipping into a taxi downtown, but we are more fearful than ever of its perils. This is the tricky thing: many well-intentioned and psychologically sophisticated parents don’t want their children to experience the freedom they did, to have the slightly too exciting experiences they had in school. They want their teenagers to be innocent and safe, but safe in this context may be another way of saying “controlled”.

When anyone these days invokes the word “safety”, as in “I was just worried about his safety”, any line of questioning or critical thinking is automatically shut down. Who doesn’t want teenagers to be “safe”? Who can argue against the absolute or obvious good of safety? But the cultural concern for our teenagers’ safety may have become a little overblown, a little existentially weird. We may be worrying too much about the safety of normal, responsible kids who are perfectly well equipped to navigate the temptations and dangers of the teenage demi-monde. I also wonder if on a deeper level some of what we are worrying about is not, in fact, their safety, but their growing up.

Sherry Turkle, a psychologist and professor at the Massachusetts Institute of Technology who has spent 30 years studying our relationships with technology, says that she has come across teenagers in her research who are incredibly upset about their parents monitoring them. She has seen teenagers who buy disposable phones to evade the monitoring of their smartphones. “Adolescence is an age of experimentation. Kids need to be able to try on and cast off personalities, to try out ideas, to fall in and out of love, to navigate the world like Huck Finn on the Mississippi and to do all this outside of parental scrutiny.” It is too soon for substantive research into the effects of increased surveillance on teenagers but she believes it is harming them: “Everyone thinks we are living in an age of emergency, but we need to ask ourselves what are we creating out of our sense of crisis?”

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On the other hand, what happens if your child is not a normal, responsible kid? The shades of difference are sometimes hard to measure in those self-dramatising years. A haunting anecdote from Andrew Solomon’s book, Far From the Tree, comes to mind. He interviewed the parents of Dylan Klebold, one of the shooters at Columbine, who killed 13 innocent people, and they had absolutely no idea that their son was in such trouble. They were, according to Solomon, exceedingly responsible, empathetic, involved, educated parents, and yet they had no sense at all of the violence brewing in their son.

This is at once shocking and not shocking: how well do we know the people we love? Or rather, if you love someone, aren’t you capable of huge and mysterious amounts of romantic delusion, of denial, of giving them the benefit of the doubt? Some tiny part of me thinks, if the Klebolds had only had eBlaster, they would have known and stepped in. How many kids would be saved by our knowing more than we technically should know? If your child is authentically in danger, real danger, shouldn’t you take all desperate measures to figure out what that trouble is? I think most people would, without thinking, say yes, even if the idea of becoming Big Brother makes them cringe a little.

Another mother who has put spyware on her sons’ computers tells me that she and her husband are “early adapters”. The argument is that soon we will be living in a universe where everyone puts spyware on their children’s computers, and those of us who resist are fruitlessly clinging to the old world, not to mention sentimental notions about the boundaries between people and the tantalising promise of privacy. She makes the point that nothing on the internet is “private” and that kids should get the message very early on that if they want to have a private conversation they should do it off line, off texts, in person. She actually told her sons that she is watching their computer use, but they seem to forget, or maybe block out this fact.

Mrs Orwell pointed out the echoes of this conversation with the larger cultural conversation about the government monitoring internet use. Like the Early Adapter, she doesn’t think that privacy is all that useful a concept for today’s kids. But there is a difference, surely, between the government which doesn’t care very much what a random citizen is doing on a Saturday night, and their parents, who care pretty intensely, if they are watching. This may just be me, but even as a fully fledged adult, I would rather the government read my email than my mother.

One day the Early Adapter found out that one of her boys slipped out at 2am, and confirmed her information with the doorman of their building who had footage from the lobby camera. He had met some friends. He got caught. George Orwell describes the state this boy lives in pretty accurately: “You had to live – did live, from habit that became instinct – in the assumption that every sound you made was overheard, and, except in darkness, every movement scrutinised.”

On the surface, monitoring your kids’ computers above board seems better than doing it secretly, except that you are overtly telling your children that they have no privacy, that even at midnight in the sweet luminescence of their Mac Pros they are being watched and controlled, that no click of the mouse will go unnoticed, no fleeting curiosity of theirs unrecorded, and that message may be worse than the morally complicated act of secretly spying on them. I think a 15-year-old needs to feel that they are sometimes alone, sometimes free of adult supervision, sometimes adrift in the dangerous, wild territories of the outside world, or, you know, Google …

To me the moral problem with monitoring a teenager’s internet searches, even if you are doing it for their own good, is that you are coming dangerously close to monitoring their thoughts or the ranging of their imagination. George Orwell wrote, “Whether he went on with the diary, or whether he did not go on with it, made no difference. The Thought Police would get him just the same. He had committed – would still have committed, even if had never set pen to paper – the essential crime that contained all others in itself. Thoughtcrime, they called it. Thoughtcrime was not a thing that could be concealed forever. You might dodge successfully for a while, even years, but sooner or later they were bound to get you.”

The Early Adapter tells me that she knows parents who go one step further than she does and put cameras in their kids’ rooms, a practice she herself does not approve of, except in very extreme cases. But I wonder, once you set foot on the slippery slope, once you are reading all of their chats, and monitoring all of their internet searches, is there that big a leap? Is secretly watching them try on six pairs of jeans that much more invasive then reading a romantically inflected Skype chat?

Another more minor and possibly common form of monitoring is the Find My iPhone app, which people use to find their children’s phones, and thus their children. This technology allows parents to map their location, to know if they are lying when they text, “I am on my way home.”

The Early Adapter says with surprising vehemence: “The ones that are so proud of their children, and say that they can talk to them about anything, and would be disdainful of the necessity of doing it, have no clue. They just have no idea what is really going on. The truth is monitoring is not as prevalent as it should be.”

When I talked to her recently, Mrs Orwell sounded like she is mostly finished with eBlaster. She scans it still but is considering stopping. She isn’t really finding much of interest and believes her daughter is fundamentally responsible.

In any event, our new version of the Thought Police are stylish, articulate, enlightened, engaged, internet-savvy, sympathetic. They are intelligently parenting in the new world, and we will need a very clever young Orwell to take them on.

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Katie Roiphe is a professor at New York University. Her latest book is In ‘Praise of Messy Lives’ (Canongate, £12.99).

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