The wave of sadness struck out of the blue. There I was, chatting with my son as I tucked him in for the night when his face suddenly crumpled.

"It's very hard, you know," he moaned.

"What is?" I asked, alarmed.

I managed to coax the sob story from him eventually.

The gist: He is one of only a few in his class - if not the only one - who has yet to play Pokemon Go.

That is just the tip of the iceberg.

At the ripe old age of nine, my son belongs to a rare breed of modern kids that has never played Minecraft; thinks Wii, Xbox and Playstation are exotic terms instead of household fixtures; and does not get a regular game fix on a smartphone or tablet.

"Whenever my friends talk about these things and I try to join in, they will say, 'Go away lah! You don't even play, what do you know?" he said between sniffles. "They say I'm lame."

Then the dam broke.

As I held my first-born close, I quickly diagnosed the problem: peer pressure. From what I gathered, the cool kids in his class tend to be the early adopters, boys who are always the first with the latest toys, games and gadgets.

Then I thought: "This is a conversation I wasn't expecting to have so soon."

I don't remember having any inkling of peer pressure till I was in secondary school. That was when I grew conscious of what separated the cool from the uncool, the haves from the have-nots.

I was full of admiration for those girls who were everything that I wasn't: athletic, gregarious, self-possessed.

I envied, too, those who seemed to have everything that I didn't: a ride to school every day in their parents' cars; branded sneakers for school sports activities; and holidays that entailed plane rides.

Now, what were once luxuries to me are staples to my two kids.

But my son, who gets driven to and from school daily, owned his first pair of Nike trainers at age seven and gets to fly somewhere for a vacation at least once a year, is feeling the angst over new benchmarks for what is cool.

Among his generation of digital natives, he is probably an anomaly, maybe even an outcast.

While we are hardly the gadget Gestapo, my husband and I do strive to keep our kids on a lean tech diet. From the start, we decided to play it safe by limiting their exposure to electronic devices.

Our rationale is: Why encourage a practice or habit with potential ill effects that you could have trouble curbing or killing later on?

Better, we thought, to put the controls in place first and slowly relax the reins when they show themselves mature enough to handle the freedom.

So our kids learnt early on that a mobile phone is neither a plaything nor a nanny, and screen time is not an entitlement but a privilege to be granted solely at our discretion.

When we are out and there is time to kill, say, before our food orders arrive, we ignore the grouses and hand out pens and paper for doodling or a few rounds of Hangman instead of passing them our phones.

Mobile game sessions - at most thrice a week capped at 15 minutes each time - have to be earned through good behaviour, such as being kind to each other or completing their homework on time without being nagged.

Now and then, my son and his six-year-old sister would ask to download certain games they hear their friends talk about.

I don't insist that these offer educational value but I will vet the content for violence, racy images and other undesirable elements.

As they grow older and their demands louder, I have had to find constructive ways to slake their thirst for a tech fix.

About once a week, I allow them up to half an hour on the laptop. They would sit next to me as I work, tapping out their latest story, Googling an interesting place or animal species they read about or viewing clip art images of something they wish to draw.

I say all these not with the smugness of someone who has expertly nailed the sweet spot between her children's online wants and offline needs, but with immense relief at somehow having stumbled upon an approach that seems to work for now.

Am I laying the foundation for a rich life beyond a small screen with these restrictions or crippling their prospects in the brave new world where technology rules?

How do I balance their desire to fit in, with the need to instil the right values, especially when they grow older and social media beckons?

I have few answers.

Gen X parents in, or approaching, their 40s like myself are in a unique position.

As Allison Slater Tate wrote in The Washington Post a few years ago, we are the last of the Mohicans - the last to straddle a life experience pre- and post-Internet.

Our generation "had the last of the truly low-tech childhoods, and now we are among the first of the truly high-tech parents", she pointed out.

This middle place puts us in a dilemma. We know it is possible to enjoy a gadget-free childhood, yet we also realise it is impractical to raise digital celibates today, especially when we can't tear ourselves from our own devices.

There is no precedent for parenting in the IT age, so my husband and I have chosen to err on the side of caution. Yes, at the expense of my son's street cred.

He missed out on Minecraft when his friends went ape over it two years ago because I didn't believe in paying for online games.

By the time I thought we could maybe give the virtual Lego-esque game a shot after reading about its possible benefits, the craze had passed, to my relief.

Pokemon Go, which took augmented reality mainstream, was another technological leap I was not ready for.

The premise of the game - essentially wandering around to catch virtual creatures - sounded silly to me.

Inconsiderate gamers didn't help its case either. Much of the initial Pokemon Go-related news I read involved players who made a nuisance of themselves or, worse, put others at risk as they went in hot pursuit of coveted critters.

After my son broke down, I read up on the game and discovered there were some health and social benefits to be reaped when played within safe parameters.

People were chalking up more exercise outdoors and clocking more family bonding time when they went hunting for the pocket monsters together.

"Okay, we can do this," I told my son the next day. "But there are rules, as always."

I will download the app if he works hard for his year-end exams. Even then, he can play only if he is accompanied by me or his father, and only within safe confines where there is no traffic. He has to stop the instant we say so.

That teary bedside chat took place two months ago. Since then, the Pokemon Go fever seems to have cooled. I'm prepared to honour my word, but I suspect the goalposts for this elusive, capricious thing called "cool" have moved yet again.

They will keep moving as my children learn to find their niche in life, just as I did.

If nothing else, I hope my son remembers our conversation that night went far beyond Pokemon: Just because all your friends are doing something doesn't mean it's right. But doing the right thing is always cool, even if your cool friends don't think so.

And no matter what changes technology brings, smart, funny and kind people will never go out of style.

Tee Hun Ching, a former editor and copy editor with The Straits Times, is now a freelance journalist.