My sister was asleep against the window when I saw the sign for the caverns. She had been asleep for maybe twenty minutes, which is not long enough to feel rested and exactly long enough that waking someone is rude. I took the exit without waking her, on the theory that she would be pleased when she opened her eyes somewhere interesting.
She was not pleased. She was disoriented and mildly carsick and she had been counting on us reaching the hotel by five so she could make a call. I had done something that felt generous and was actually just unilateral. That was several years ago and it changed how I handle every detour I have taken with somebody else in the car since.
The driver has an unfair amount of power
This is the thing nobody says plainly. The person holding the wheel decides where the car goes, and every other preference in the vehicle has to be converted into a request. That asymmetry is fine most of the time because most of the time everyone wants the same thing, which is to get there. Detours are where it becomes visible.
A detour is the driver spending everybody’s afternoon on something the driver found interesting. It can be a gift. It is a gift the way picking a restaurant for the table is a gift, which is to say it depends entirely on whether you asked. I had been treating spontaneity as though it excused me from asking, because asking would ruin the surprise. What it actually did was make my curiosity into everyone’s schedule.
Ask before the turnoff, not at it
The worst time to raise a detour is two hundred feet from the exit, because that is not a question, that is an announcement with a countdown attached. The passenger has about eight seconds to weigh something they know nothing about, and the honest answer of “I need a minute to think” is not available. So they say sure. Then they are mildly annoyed for the next hour and neither of you knows why.
I try to raise possibilities a half hour out now, when nothing has to be decided. Something like, there is a thing about forty minutes ahead that I might want to stop for, no pressure either way. That gives the other person room to say they would rather push on, and it gives them room to get interested. Both outcomes are better than the eight-second version.
Say what you actually want
The failure mode I fall into is pretending to be neutral. I say “we could stop, or not, whatever you want,” which sounds accommodating and is really a way of avoiding responsibility for the decision. The other person then has to guess how much I want it, and they usually guess wrong in the generous direction, and now we are stopping for something I only half wanted.
It works much better when I put a number on it. I want this a lot, or I am mildly curious and would drop it instantly, or I have wanted to see this for a long time and it matters to me. People are good at responding to a stated preference and terrible at responding to a fake one. My sister and I have a shorthand for it now, a one to ten, and it has resolved more roadside arguments than any amount of discussion.
Know what the other person is holding
My sister was not being difficult that day. She had a call at five and I did not know about the call, and I did not know because I had never asked what her day contained. I had been treating the drive as unstructured time for both of us because it was unstructured for me.
Most passengers are carrying something. A meeting, a person they need to text before a certain hour, a stomach that does not do winding roads, a level of tiredness they have not mentioned because they do not want to be a burden. Ten seconds at the start of the day, asking what has to happen and when, buys enormous freedom later. Once I know the hard edges of someone’s day I can detour freely inside them without checking every single time.
The detours that work for two people
Something I did not expect. The detours that go best with a passenger are usually not the ones with the most impressive destination. They are the ones with something to do at the end of them. A place to walk around, a counter to sit at, a thing to choose between. Standing in front of a view together is fine for about four minutes and then one person is ready to go and will not say so.
The other reliable one is the detour the passenger picked. Even a mediocre stop lands better when it was their idea, because they are invested in it working out, and because it rebalances the day a little. I try to make sure at least one turn per trip is not mine. It costs me nothing and it changes the whole texture of the car.
What I would say to myself at that exit
If I could go back to the caverns exit, I would not tell myself to skip it. The caverns were fine. I would tell myself to wake her before the exit rather than after it, which is a smaller and more annoying piece of advice than “be more considerate” but is the entire difference between the two versions of the afternoon.
We did the caverns. She was polite about them. On the way out she said the thing I still think about, which was that she would have been happy to go if she had known it was coming. Not the detour, then. The ambush. I had been so pleased with myself for being spontaneous that I never noticed spontaneity is only free when you are alone in the car.