take everything that i say with a grain of salt. i've been trying to theorycraft interpersonal relationships for quite a time, and this is just what has helped me develop a more confident mindset.
other people will generally give you advice along the lines of putting yourself in social conditions which call for you to forcibly adapt. i think this is all well and good, but it's my belief that you can streamline the process. i think that, contrary to what others say, it's
good to be conscious of how you operate socially. you shouldn't allow yourself to become someone who has to suffer unneeded social losses: appearing awkward
shouldn't be a concern, but it unfortunately
is for most; hence why we develop habits of practice which try to accord with standard social norms. not every social setting can call for subverting these norms. at parties, for instance, it's expected of you to interact with others freely. you might even say that it is an imperative; conversing freely in a social setting where it is not socially accepted, however, and not obtaining preferred outcomes, is a subversion of norms, and, even if marginally, can result in social incursions or generally negative outcomes.
now, the idea is not to be overly conscious of these facts, since that can result in a stunting of progress. obviously you aren't going to become an extremely sociable person over night, and you may not even have the opportunity at all to become as sociable as, say, a comedian.
in my opinion, the proper attitude is a sense of realism; people gravitate those with socially desirable traits, and consequently we base our behavior on social wants that we perceive. modifications that we may make to change how we are perceived by people will result in forming an ideal which we strive for; that is, an ideal which we gather from social report and observation. we can then take people around us and compare them to our ideal: how can they communicate so well? why do they have so many friends? is this what i want? if yes, then accordingly we need to go through a 'guessing' process of sorts: perhaps because he possesses X qualities, which may or may not be superficial, this will help me closer to my ideal.
an ideal must be built from practice, however, and not theory. one should rarely ever try to equate humans to the same caste; that is, no overarching theory of human nature can ever bear more fruit than the bare minimum for theory (theoretical standards which we hold for ourselves, perhaps). so, in this case, the only measures we should be thinking about are how to reduce losses in the
worst possible scenario. in other words, we can derive some value from the highs we experience, and still be consistent, since we are ready to deal with the lows, or at least prepared enough, and consequently prejudging how a low may occur (maximin).
i do not consider myself terrible looking by any means (just an ugly personality sometimes) but for some reason i cannot mentally figure out how to interact when i am not expecting the interaction. i have to rehearse and plan out possible things that they would say to me. i have conversation questions loaded up if i know im going to be hanging out with someone that day. i hate it and its going to drive me insane.
basically everything that i've said equates to this: you can figure out some habit of social practice, but you can't take it to any theoretical maximum, which will actually impede obtaining preferable outcomes in practice (or even impede action). anticipating social responses is inherently unpredictable. theory can only get you so far without practice: they should be interchangeable. so in this case, you can figure out some structure of conversation through trial and error; it's a springboard, and thus in the future may not even be necessary, as at that point your probably equipped to deal with situations based on the expected value of the outcome. don't think about the minutiae, but rather of the course that a conversation might flow. if you overthink it, you might stunt the natural flow of conversation.
instead, try having loose guidelines in mind: i can't define these exactly, since you need to figure out what works best for you via practice, but an example for me would be that i let people talk about topics they are knowledgeable in, or of reaching a certain end-goal in our conversation. it usually flows naturally; so when we merge theory and practice, it's a change in your mentality going in, not during. suspend all judgements that you may have of another person, or of what judgements they have of you, they are useless. only judge what is
given, that is, which presents itself in a material way; if i strike out with this person, then there's a
reason, and therefore i should try to guess at what i did wrong for the future. this might not mean that you actually did wrong, since it could be a problem that rests upon them. but with practice you will begin to optimize these modifications to find what is and isn't on the other person.
something else to add is that even if we anticipate social incursions that arise from breaking norms, we shouldn't view a blow to our self-esteem as a loss; in fact, we shouldn't treat our minds (mental health) as an object of consideration in practice. if you look at it through the prism of net loss (which is permissible, since it allows us theory which easily translates into practice without making too many assumptions), you will only suffer net losses from trivial interactions (which are within the realm of normality) through a loss to your ego. if you suspend the idea of the ego as an object of your consideration, then you don't suffer any real losses. again, what value you obtain from any interaction is largely dependent on you. you never miss an opportunity if you strike out with someone, since that will contribute to developing more stable habits of practice.