Here is the thing nobody mentions about dating in this country: we get two completely different years. For about half of it you can suggest a walk without thinking twice. For the other half, "let's meet outside" is a small act of cruelty. So the honest answer to "where should we go" is that it depends what month it is.
What does not change is the job a first date has to do, which is smaller than people think. You are not auditioning. You are finding out whether you would like a second one. That means somewhere you can hear each other, somewhere neither of you has to drive an hour in bad weather, and something with a built-in ending so nobody has to invent an excuse. Six that work.
Everybody knows how dinner works, which is exactly why it is the default. The mistake is treating the restaurant as decoration. What actually decides whether the evening works is whether you can hear each other, and a hard-surfaced room with music on will have you both nodding at sentences you did not catch. Phone ahead, ask for a quiet table, and go early rather than late. Also think honestly about the driving. A place ten minutes from you in July might be forty in February with the roads the way they get, so pick something between you rather than something near you. And if a whole dinner feels like a long first commitment, lunch does the same job in half the time.
Walking is the most underrated first date there is, because you are side by side instead of staring at each other across a table, and there is always something to look at when the conversation needs a rest. You do not need real countryside. A rail trail, a conservation area, a stretch of the Trans Canada Trail or the boardwalk at the lake will all do. Pick something flat and agree the distance beforehand, so nobody is quietly regretting their shoes at the halfway point. Bring the dog if you have one. You will know inside two minutes whether they are a dog person, which is more than some couples work out in a year.
This one solves the problem everybody actually worries about, which is running out of things to say. On a tour you do not have to generate conversation, because it keeps arriving through the window. It is obviously good if one of you has just moved, but it is better than you would expect between two people who have lived in the same city for forty years, because the guide always turns up something neither of you knew. Sitting down is built in, it lasts a set length of time, and it ends by itself.
The old objection is that you cannot talk during a film. That misses what the film is for. It is not the date. It is the thing that gives you a subject for the coffee afterwards, which is the actual date, and it means neither of you has to arrive with material. The economics are good too. Cineplex runs a cheap Tuesday nationwide, Landmark puts its seniors day on a Monday with a discount on the concession as well, and most chains set the seniors rate at 65. Weekday afternoons are half empty, which is a large part of the appeal.
Half an hour in a rented rowboat is the most efficient icebreaker on this list, for one reason: you will both be visibly bad at it. Nothing dismantles first-date stiffness faster than two people in their sixties going in a slow circle and laughing about it. It also has the right shape. Half an hour is long enough to get properly talking and short enough that if it is not working you can shake hands at the dock without anybody feeling trapped. Somebody will get splashed. It has never mattered.
Not romantic. Extremely effective. A big garden centre gives you two easy hours with a built-in structure: something to look at the whole way round, a cafe in the middle, and no requirement to be charming on demand. In this country it also lands at exactly the right moment, because the planting window is short and everyone is thinking about it at once around the May long weekend. Sheridan in the GTA and GARDENWORKS in BC are the obvious ones, but the independent down the road is just as good. Buy them a herb on the way out. It outlasts flowers and costs less.
One last thought that applies whatever the month. If you cannot decide, coffee at Tim's is not a cop-out. It is cheap, it is everywhere, it takes forty minutes, and nobody has ever felt overdressed for it.