For the second situation, it isnt always that they want to be asked the question. Sometimes they noticed a change in your behavior recently and are checking in on you.
Example, you’re eating lunch and you love chocolate pudding. You usually eat your chocolate pudding every day without fail. Today, you didn’t eat your chocolate putting and just left it sitting there.
A: “Hey” B: “Hey” A: “So… what’s up?”
Regardless, “what’s up” is just a place holder for “how are you”. Sometimes that is just small talk and a way of fulfilling simple social interaction, and sometimes it is a question with genuine interest in knowing what is going on in your life (or asking you first, so they feel comfortable sharing what is going on in their own life).
I always find it easiest to give a simple and short, but honest, response, and elaborate further if they show interest with follow up questions. Of course, giving them information you are comfortable giving that person.
A: “What’s up?” B: “Not much, I’m a little tired today. You?”
or
A: “What’s up?” B: “Kind of sad, but I don’t want to talk about it.”
If you go in with that attitude, though, are you there to try to convert people to your side. Or are you only there to berate them and make yourself feel better for having done so?
That doesn’t mean you put up with bad faith engagement. That doesn’t mean you allow them to burden you with the emotional and mental weight of the argument. That they can watch the consequences without fear of it harming their self is exactly why you need to watch your language. They lose nothing staying where they are, you need to convince them to give up resources (mental, emotional, financial) of their own to take up your position.
So, don’t put up with bullshit, and you don’t have to be nice about it, but you do have to be patient of your goal is to actually convert people over. Not everyone’s role is to convert people, though, some people are only fighters. Just make sure the fighting is directed in the right places.