Where's that line?

How do we find out if we our concern, genuine though it might be, had not overstepped what's appropriate among colleagues and friends?

How do we find out, beforehand if possible, that our caring will not cause any awkwardness or discomfort when expressed?

Where do we draw that line? How do we determine that line?

It's easier with those who speak frankly, talk directly, and candid about such things. You know, yes is yes, no is no, enough is enough, those who will simply tell you what's on their mind, like "time's up", "I am going to kick you now", "slap you ah!", "enough, I don't want to hear anymore", "eh, too much, stop!", "this is private", "I don't want to discuss that with you", et cetera.

I am more comfortable with these people. These are my kind of people. ^_^

On the other hand, those who are reserved, speak sparingly, those who always left you wondering or guessing... my goodness, I find it taxing to communicate with this kind of people.

Never quite know if I had unintentionally offended or said something inappropriate, something sensitive to them. And sooner or later the doubt and uneasiness would built up that I would ask them to stop me or inform me when I have gone too far.

I guess this is just part of social skill set, which I admit I am not all that good at. After all, I am borderline antisocial most of the time.

A people person I am not.

Oh well, I suppose as long as it's genuine care and concern on my part, I will blurt it out anyway, incredulous stare or awkward silence be damned.