My oldest is 16. That sounds fine until you do the math. Less than two years of high school, then whatever comes next. Suddenly, a number I always thought was safely in the future doesn’t feel that way anymore.
So I’ve been putting together my own bucket list ideas for teens: things I actually want to do with my boys before they’re gone. Some are big. Some are embarrassingly small. A few of them my kids will absolutely not want to do, and I’ve decided I don’t care.
The thing about having teenagers is that you spend so much time managing the day-to-day that the bigger picture sneaks up on you. One minute you’re arguing about dishes. The next minute, you’re realizing you haven’t done anything worth remembering in months.
I’m not building character. I’m buying time.
1. An overnight canoe trip in Algonquin Park
Just the two of you, a loaded canoe, bad food, no cell service. They won’t want to go. Something about no signal and sleeping on the ground. Go anyway. The point isn’t the paddling. It’s the hours with nothing else to do but talk, or not talk. You figure out pretty quickly which one you both actually needed.
2. A road trip with no real destination
Pick a direction and drive. Let them control the music. Car conversations hit different. Something about not making eye contact makes everything easier. You’ll cover more ground in two hours on the highway than in two months of sitting across from each other at the dinner table.
3. Watch every Christopher Nolan film in order
It’s a commitment. They’ll tell you it’s too long, too serious, and they’ve already seen some of them. Watch them all anyway, in order, one or two at a time over a few months. They’ll have opinions by the end, and that’s the entire point. Arguing about Interstellar on a Saturday is time well spent.
4. Teach them to cook one thing properly on the Big Green Egg
Not just throw it on and hope. A real cook. Knowing the temps, managing the fire, and understanding why patience matters. If you’re not sure where to start, there are good entry points that won’t overwhelm them.
5. Go to a Blue Jays game, just the two of you
Not a family outing. Two seats, somewhere decent, in the middle of a Tuesday afternoon with nothing else happening. No plan after. Three hours where the only thing required of either of you is paying attention to the same game.
6. See Niagara Falls
I know. It sounds like the kind of thing you keep putting off because it’ll always be there. It won’t always be there to do together. It’s two hours from Toronto, genuinely impressive in a way that doesn’t photograph well, and you can be home for dinner. Just go.
7. Take the overnight train somewhere
VIA Rail, Toronto to Montreal. They’ll ask why you’re not just flying. Tell them to look out the window. Let them stay up too late watching the dark countryside go past. There’s something about being in motion with nowhere to be that makes people talk. It costs less than you think, and they’ll talk about it more than the flight would have been worth.
8. Let them drive in an empty parking lot
Before they have their licence. Find somewhere quiet on a Sunday morning, hand them the keys, and try not to grip the door handle too obviously. It’ll be the most terrifying twenty minutes of your life and they’ll be grinning the entire time. They’ll remember this one.
9. Watch the Perseid meteor shower
Peaks every August. Find a dark sky site north of the city where you can actually see it. NASA tracks the exact peak dates. Muskoka, Haliburton, anywhere past the light pollution. Set the alarm for 2 am. They’ll groan about it the night before. Get them up anyway. Standing in a field at 2 am watching the sky with someone you made is worth a rough morning.
10. Take the ferry to the Toronto Islands for the day
It’s 15 minutes on the ferry and costs next to nothing. Half the city has never actually gone. No plan needed once you get there. Just go and see what happens.
11. Tell them the actual story of how you met their Mom
Not the clean version. The real one, with the details. They’ll say it’s cringe. Tell it anyway. They’re old enough, and they’ll think about it later.
12. Go to a concert, their choice, their music
Sit through whatever they’re into. Don’t make a face. Don’t check your phone. Ask questions after. You’re going to hear things you don’t understand, and that’s the whole point. Let them explain it to you.
13. Teach them to tip properly
This sounds small. It isn’t. They’re about to be out there handling tabs on their own, and there’s a right way to do it. Better that they learn it from you before that happens.
14. Ottawa for a weekend
The Rideau Canal, Parliament Hill, and the ByWard Market. They’ll think it sounds like a school trip. It’s not. It’s one of those places that sneaks up on you, and it’s genuinely Canadian in a way that doesn’t feel forced.
15. Fix something together
Bike, furniture, leaky tap, whatever. The project doesn’t matter. There’s something about working side by side on a problem that cuts through the usual friction. You’re not a parent and a teenager for a couple of hours. You’re just two people trying to figure something out.
16. Cook a proper dinner; they’re in charge, you assisting
Not frozen pizza. A real dinner for the family. Pick something that requires actual effort, set them up to succeed, and then get out of the way. The mistakes are part of it.
17. Watch a terrible movie and critique it the whole way through
Pick something genuinely awful. Bring snacks. Some of the best conversations happen in the wreckage of a bad film, when you’re both making fun of the same thing, and nobody has a point to make.
18. Do one Toronto thing you’ve been putting off forever
Pick something from this list that you’ve walked past for years and never actually done. Book it. Go.
19. Go somewhere they pick, with no input from you
Restaurant, activity, neighbourhood, whatever they want. No input, no alternatives, no “are you sure?” Just go. You’ll end up somewhere you’d never have chosen, and that’s exactly the point.
20. All-you-can-eat wings until someone taps out
It’s stupid and great. There’s no lesson here, no bonding framework, no growth opportunity. It’s just two people eating too many chicken wings and seeing who taps out first. Sometimes that’s enough.
21. The CN Tower glass floor
If they’ve never done it, they need to. It takes about ten minutes, costs less than you think, and Toronto looks genuinely impressive from up there. Do it on a clear day.
22. Stay up too late doing nothing productive
Video games, bad TV, talking about whatever comes up. No agenda. No bedtime debrief about how the day went. Just being in the same room past midnight for no good reason, which is the best reason.
23. Take a photo together that doesn’t look like a photo
Not the Christmas card one. Something candid, something real, something that actually looks like you two. They’ll groan and make a deliberately terrible face. Do it anyway. You’ll want it later more than they’ll mind it now.
24. Tell them you’re proud of them, specifically
Not “I’m proud of you for everything.” That lands like nothing. Pick one specific thing, something you noticed that they didn’t think you were paying attention to, and say it directly. It matters more than you think.
25. The standing breakfast run
Find a spot near your house that serves a good breakfast. One that doesn’t have a lineup every weekend and has decent coffee. Make it a standing thing. Weekly, monthly, whatever the schedule allows. The ritual matters more than the food. That’s true of most things on this list.
The list is going to look different for every family. Some of these won’t fit yours, and you’ve got things on your own mental list that aren’t here. If you want more on making the most of the time you’ve got with teenagers, there’s plenty here.
The point isn’t the list. It’s that the window is smaller than it looks from where you’re standing now.
Start somewhere.
