There’s already some phenomenal advice above by some great people. I’ll share my abstract version/mindset advice that helped me whether or not specific to situations, for I can understand and relate to some of the things you talk about, and I still think too much sometimes!
The better I’ve become at viewing things in life objectively, (after what’s been far too long of an emotional roller coaster followed by a burn out into almost cynicism over the past years of my life, then landing into a positive outlook from within towards the rest of life), the less intense and often are the random thoughts, or “stories” as I now call them, that I get in my mind of “this person thinks this”, or " I should’ve done that, now x=y," in the social context, be it really important family, relationships, business. I share the most IMPORTANT thing that’s helped me-
Build your self esteem! Build the self confidence that is SOURCED AND SUSTAINED BY YOU!
For me, I realized that although I’ve never been petty at all, “insecurity” is a vast trait and good people can have insecurities too, and I had quite a mountain of insecurities. I soon couldn’t even reason what was an insecurity I was living and what was a real/addressable issue.
I set to work on them, chiefly by letting go, made positive affirmations and worked on my confidence, also confident that I’d never let ego take precedence and that I can still have the confidence I deserve and yet never be one for boasting. I found something amazing happened. As soon as I had removed all these senses of insecurity and boosted my personal confidence as well as broadened my perspective and thought about people more objectively with less expectations, I was free! Public speaking was easier, all relationships were healthier or at least easier to navigate and I wasn’t invested to a toxic degree in anyone, I didn’t care for anyone’s approval (yet still found love for people because it was clear of self), and the irrational, meaningless stories about what people surely thought or felt about me disappeared, and even if I were to be right on a rare occasion about someones negative perception, and if it was from someone I really cared about or in family even I realized it was about them as they view their life through their first person lens and nothing is ever about the identity of me, besides me. Only we can see our life through our own first person lens, and other people are seeing through theirs, so us seeking other people’s approval to the degree that we speak of is simply an old tool for development and acquisition that once helped us before we were self aware as a very young child, but we soon grow out of the need for this habit and we tend to hold on to these things when we don’t need them anymore for far too long! Hope that helps, and makes sense, I have a hard time making shorthand what I try to say:
Love yourself, grow your well of confidence, and the deeper it is thus the clearer the pool of your broad and wiser perspective of the world, see the truth behind the great advice of ‘don’t take anything personal’, and the more confident in yourself you are the magically easier it is! You won’t be worried about others approval so much. Things in life won’t be awkward because you flow with everything because you’ve got YOU taken care of! You are awesome. If I can grow out of a similar stressed mindset in an emotionally tough family situation, there’s no doubt in my mind you can! But what matters is that there is no doubt in yours. 