Knock on wood, but i feel like I've finally left the agonizing part of life when you realize that you've said something dumb immediately after you say it and so live in a perpetual state of cringing at yourself.
When I was a teenager, I was blissfully ignorant that I'd said something dumb until hours to days later, so tended to have my moments of cringe late at night and all at once.
In my early twenties, I spent my life in a constant state of embarrassment, trying to shove words back into my mouth as I realized a statement was tactless/offensive/mean/weird/etc. as I was saying it, and then needing to immediately apologize.
Now, it feels like I'm able to recognize that it would be a bad idea to say something before I say it, and so am able to significantly reduce the amount of cringe in my life. Hopefully I can keep this up until I get dementia in my old age <3