I’ve always been a supporter of a regret — a regret-booster, as it were. I think regret is a pretty cool thing. It’s great. It teaches you things. It’s like history. We regret in order to not repeat the mistakes of the past. My regret can beat up your regret. Et cetera.
This position was mostly in reaction to the use of regret by morons as an excuse for all kinds of moronity. “No regrets!” rings the clarion call before the frat boy slams a liter of homemade vodka and runs into traffic.
The simple truth is, regret isn’t that simple. In fact, it’s so complex that one could think oneself in circles indefinitely, frozen in a perpetual state of What if? One could do that. If one were so inclined. Hypothetically.
And that’s what regret is all about, really. What if? What if I’d done this? What if I hadn’t done that? How would things be different? The conventional wisdom (that of the flattened frat boy) seems to be, it’s easier to live with the consequences of your actions than with those of your inaction. It’s better to have loved and lost, than never to have loved at all. It’s better to regret the things you did do rather than the things you didn’t.
The assumption is that knowledge is preferable to speculation, even if that knowledge is not particularly happy. Or maybe it’s some kind of humanist ideal, where if you take some action — any action — at least you’re taking part in shaping your own destiny, instead of just letting it happen to you.