[wallflower]

I've recognized that what holds me back is what I fear and in some cases I feel default non-optimal social habits are my default because I am addicted to the feeling of being a lone wolf, the wallflower in a social situation.

As you point out, hacks only work if you iterate on them. You can't unit test social graces you can only have good exception handling. And good exception handling may come down to experience handling situations earned by actual trial-and-error and as this article says - a certain amount of cockiness.