Dad, Do You Want to Play?: The Question I Wish I Had Said “Yes” to More Often
Caveat: This is a deeply personal article for me to share. Writing it brought back memories from my life as both a father and a police officer, some of which I had not reflected upon this deeply for many years. Revisiting those moments stirred emotions that I wasn’t necessarily expecting when I first sat down to write this piece. Some of the memories brought a smile, while others brought regret and the realization that there are moments in life, particularly as a parent, that we simply cannot get back. I share these experiences not because I am proud of every decision I made, but because I hope that by being open about some of my own mistakes, another parent or caregiver might recognize an opportunity to make a different choice while they still have the time to do so, especially in today’s extremely busy onlife world.
Recently, I was asked an interesting question by the parent of an elementary school student. During our conversation, my age came up. When I told her I was 61, she looked surprised and said, “No way, I thought you were in your mid-50s.” I’ll admit, that was a pretty good ego boost, but what she said next really stuck with me. She told me she was surprised that someone my age was so current and knowledgeable about what youth and teens are doing online today. I laughed, and shard that teens call me a “Drippin Boomer” (a cool older guy), but her comment caused me to reflect on how I got here, and more importantly, on something I wish I had done differently as a father.
When the Job Became Too Important
I am a husband, a father, and a retired police officer. I spent more than 30 years in policing, much of it dedicated to helping, protecting, and educating others. When I retired about ten years ago, I knew I wasn’t finished with prevention and education. I simply shifted my focus toward helping young people, parents, caregivers, educators, and others better understand technology and the onlife world our kids are growing up in.
There is another important part of that story, however, and his name is Brandon. Early in my policing career, I became extremely focused on my profession, particularly in the areas of police use of force and control tactics. Eventually, that dedication to my work took me internationally as a subject matter expert. I travelled, taught, researched, trained, wrote, and lived the job. At the time, I saw that dedication as something to be proud of. Looking back as a 61-year-old father, I can now see what that dedication sometimes cost me, meaningful time with my son.
“Dad, Do You Want to Play?”
There is one memory that still comes back to me. When Brandon was in elementary school, he loved video games. One of his favourites was a James Bond 007 game. I can still remember him coming to me and asking, “Dad, do you want to play?” Sometimes I said yes. Far too often, however, I had a reason why I couldn’t such as I had work to do, something needed to be written, someone needed to be called, I was preparing for training, I had another project to finish for work. There was always something that seemed more important at the time.
What I didn’t fully understand was that when Brandon asked me to play a video game, he wasn’t necessarily just asking me to play a video game. He was inviting me into his world. Given what I do today, I now realize that distinction means much more to me today than it did back then.
As adults, we sometimes judge an activity by how important it seems to us. A video game might look trivial compared with a work deadline, an email, a report, or something else demanding our attention. However, to our child, that game might be where they are having fun, developing friendships, overcoming challenges, competing, creating, laughing, and spending time with the people who matter to them. When they ask us to join them, the real invitation may be, “Come spend some time with me.” I now wish I had understood that better when Brandon was younger.
This is probably the hardest part of this article for me to write. I cannot recover those afternoons and evenings. There is no rewind button for parenting. I can’t go back to elementary school Brandon, put my work aside, pick up the controller, sit beside him and say, “Okay buddy, let’s play.” However, today I recognize that this is what I should have done!
There are many things in my life and career that I am proud of. There are also things I would do differently, both personally and professionally, if given the opportunity, and this is one of them. Today, however, something pretty wonderful has happened. I feel Brandon and I are closer than we have ever been. His interest in digital literacy, technology, and internet safety eventually became both an academic pursuit and a career. It also created an opportunity for the two of us to work closely together and build a father-son relationship that, at times when he was younger, I acknowledge wasn’t as strong as it should have been.
Today, I jokingly refer to Brandon as my “Digital Yoda,” while I’ve happily taken on the role of his “Digital Padawan.” Somewhere along the way, the roles reversed. I’ve passed the torch of The White Hatter to him, and today Brandon serves as our CEO which, technically, means my son is now my boss. Ah yes, as I like to say, “the circle of life has officially come full circle!” As a father, I couldn’t be more proud!
However, behind the humour is something incredibly meaningful to me. I get to spend time with my son doing something that both he and I are passionate about, learning from him, supporting him, debating ideas with him (and debate we do), watching him roll his eyes, sigh, and shake his head at some of my thoughts and ideas, travelling with him, presenting with him, and hopefully creating new memories together. I can’t change the memories we didn’t make, but I can still create the memories that come next.
A Message to My Son
I know Brandon will eventually read this because, at some point, he reads pretty much everything I write. So Brandon, this part is for you, I love you, son!
I also acknowledge that there were times when you were younger when I should have been more present. There were times when you wanted your dad to sit down, pick up a controller, and play a game with you, and I allowed my work to become more important than the moment you were offering me. I wish I could turn back time and change some of those decisions, I can’t.
What I can do now, however, is support you today and continue to be part of what you are building if you allow me to. My hope is that the memories we are creating now, with you at the helm of the White Hatter, will become some of the memories you carry forward long after I’m gone. So far, I am loving the journey we are having together, as I hope you are as well, even though I know sometimes you just shake your head.
Parents, Don’t Miss the Invitation
I share this story because there may be a parent or caregiver reading this who is currently living through the stage of parenting that I now look back upon. Your child may be sitting in the next room gaming. They may be creating something in Minecraft or Roblox. They may be excited about a YouTube creator you have never heard of, showing you a ridiculous meme that makes absolutely no sense to you, experimenting with artificial intelligence, listening to music you don’t particularly enjoy, or talking endlessly about something happening in an online community you know nothing about. It can be tempting to dismiss those moments, try not to.
You don’t have to love everything your child loves, and you do not need to become a gamer or an expert on every app, platform, meme, online trend, or new piece of technology that enters their world. Trying to keep up with everything our kids are doing online can feel overwhelming, and the reality is that most parents never will. What matters far more is showing genuine curiosity about the things that matter to your child and being willing to occasionally step into their digital world rather than always expecting them to step out of it and into ours.
Ask your child to show you what they are doing and explain why they enjoy it. Sit beside them while they play their favourite game, watch a video together, ask about the people they interact with online, or let them explain why a particular creator, meme, game, or trend is so interesting to them. You don’t necessarily have to understand it or even enjoy it yourself. Sometimes simply watching, listening, playing, laughing, and sharing the experience communicates something much more important, “What interests you matters to me because you matter to me.”
One of the most powerful things a parent or caregiver can say to a child when it comes to technology is, “I don’t know how this works. Show me.” In that moment, something interesting happens. Your child becomes the expert (Yoda) and you become the student (Padawan). They get an opportunity to teach you, demonstrate what they know, and share a part of their world with you without immediately feeling that they are being monitored, judged, or lectured.
These seemingly small moments can become important opportunities for connection. They create conversations, build trust, and help parents better understand what their children are actually doing online rather than assuming they know. More importantly, they send a message that you are interested in being part of your child’s onlife world, not simply policing it from the outside. That’s relationship building, and relationship building can become one of the most important foundations for helping keep our kids safer both online and offline.
Connection Is Also a Safety Strategy
There is another reason this matters. Meaningful parental engagement with a child’s digital life isn’t just about creating memories. Research into parental mediation and youth technology use generally supports the importance of active, engaged approaches that include conversation, shared experiences, guidance, and communication rather than relying exclusively on restrictive rules or technological controls.
This doesn’t mean that involved parents can prevent every online problem, the realty is they can’t. It also doesn’t mean boundaries aren’t necessary, they absolutely are. However, a child who regularly talks with a parent about what they are doing online has something extremely valuable when something eventually goes wrong, a trusted adult they already know they can talk to.
That’s important because the first time we show genuine interest in our child’s digital world shouldn’t be after something bad has happened. If every conversation about technology sounds like:
“Put your phone away.”
“Get off that game.”
“How long have you been online?”
“Who are you talking to?”
“Give me your phone.”
then we shouldn’t be surprised if our children eventually conclude that technology is something they need to hide from us rather than something they can talk to us about. Safety isn’t built only through parental controls. It’s built through relationships and something I like to call the “human element”.
At The White Hatter, we often speak about the importance of relationship before dependency. Technology should never replace the parent-child relationship. However, technology can absolutely become a place where that relationship is strengthened. Co-play, co-view, co-create, and explore their online world together.
Let your child teach you about their favourite game. Ask them about the people they play with. Have them show you the funniest video they saw this week. Experiment with an AI tool together. Ask them why everyone at school suddenly seems obsessed with a particular app. Those small interactions may seem insignificant, they’re not. They’re deposits into a relationship bank account. Later, when your child encounters cyberbullying, sexual content, harassment, manipulation, an uncomfortable message, a scam, a stranger asking inappropriate questions, or simply something online that scares or confuses them, you want them thinking, “I need to tell Mom”, “I need to tell Dad”, and “I need to tell my caregiver” rather than, “If they find out, they’re going to freak out and take everything away.” That trust is built long before the crisis occurs.
The Controller I Wish I Had Picked Up
If I could speak to the younger version of myself, I wouldn’t tell him to abandon his career or stop pursuing the things he was passionate about. I’d simply tell him something I didn’t understand well enough at the time, “The work will still be there tomorrow. Your child’s childhood won’t.” There will always be another email, another project, another deadline, another report, another presentation, and another reason to say, “Not right now.” However, eventually, something happens that nobody warns you about, “One day, your child stops asking, they grow up.”
Today, I am fortunate. The little boy who once asked me to play James Bond 007 with him grew into a man I admire, work alongside, learn from, am in awe of specific to what he can do with technology, and most importantly love very much. I can’t go back and pick up that controller, but perhaps another parent reading this can with their child.
So when your child walks into the room tonight and says, “Hey, want to see something?”, put down your phone, close the laptop, take a few minutes, and enter their world. Because twenty or thirty years from now, you probably won’t remember the email you were answering, but you might remember the game you and your child played together. More importantly, so might your son or daughter - Just saying!
Darren
