Scheduling with flaky people is prisoner’s dilemma.

When someone you know can change plans on you at any time, it disincentivizes reliability. Sure, you could hold on to some ideal of being honorable to your word. But if there’s a 50% chance the person will cancel—and you’ve made your plans around them—you’re left holding the bag. They get flexibility, you get friction.

It’s not a perfect mapping to the actual game theory, but the dynamic echoes the prisoner's dilemma.

Quick refresher if you’re not familiar: in the prisoner’s dilemma, two people are offered a deal. If both cooperate, they both get a decent outcome. If one betrays while the other cooperates, the betrayer wins big and the cooperator loses. But if both betray, both lose. So the temptation is to protect yourself—even if it sabotages mutual benefit.

That’s kind of how scheduling with unreliable people works. You want to trust, but if they flake, you’re the one who loses.

This happened to me today. I woke up at 6:30, planning to go into work early with a colleague. I was giving him a ride. I structured my whole morning around that: skipped the gym, rushed my writing, sacrificed sleep—because I thought we were on. Then I checked in, and he said he’d already left.

Not worth something getting angry about. But it’s worth naming the dynamic. When someone can pull out at any time—and you’ve structured your morning (or week, or emotional energy) around them—it naturally makes you less inclined to commit next time. You start defaulting to "soft yeses" or vague agreements. You start mirroring the flakiness.

There are ways around this. You can pre-commit more clearly: “Hey, I’m planning my morning around this—are we definitely on?” Or you can state your reliance upfront, which makes it more likely they’ll either show up or give you an early heads-up. Not in a guilt-trippy way, just in a clear-expectation way.

Low-stakes plans often invite casual rescheduling. And that’s fine—we’re all free to change plans. But the game theory behind even these micro-decisions shapes how we move through the world. If you understand the dynamics at play, you can adjust your approach: insulate yourself, build in backup plans, or stay loose enough not to be knocked off balance.

When you understand the game, you get to play better.