On a more mental level, there are a few seemingly random subjects that make me flinch and feel burning shame whenever brought up, because almost a decade ago I happened to make a fool of myself in conversations that involved them; yet those were by no means the most sorrowful moments of my life, or even the most embarrassing.

Regret management seems to get more important with age. The fuckers accumulate.

One thing I do is remind myself, "I want to be the kind of guy who's cool with having done that." And, if possible, "It was an inexpensive lesson that it was good to learn." Do affirmations like that have any impact on your regrets?