I started listening to
A Nerd of Advice today, which bills itself as an etiquette guide for nerds and is co-hosted by an author I really enjoy.
It felt oddly...prescriptive, to me, and occasionally suggested basically impossible things. (You can guess what someone's intention is when they say or do something, but you can never actually know.) The impression I got -- recognizing that impression is not intention and what I heard is not necessarily what they meant to say -- was that social rules are really really really complicated but if you work really really really hard, you'll never have to deal with awkwardness again.
It got me thinking about my own internal etiquette guide, which is less a guide and more a cost-benefit analysis. There are no right or wrong answers; it's what feels right for you.
Simplistic example:
Somebody talks to you in a way you don't like. If you speak up, you can get the behavior to stop, but you might be seen as a bitch. If you don't speak up, the behavior will continue, but you'll be seen as a nice person.
You weigh the result (getting the behavior to stop) against the cost (no longer being seen as nice) and decide whether it's worth it to you. Sometimes social conditioning or anxiety or other things make it hard to make that evaluation with a clear head, in which case things like therapy can be helpful.
But only you can decide what you value, and what price you are willing to pay for it.
Also, awkward is inevitable, and an awkward conversation is not the worst thing in the world. If I were to write a book for my internal etiquette, on the cover, printed in big, comforting letters, would be "AWKWARD IS INEVITABLE. Don't panic."