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> However I'm now in situations where the world is divided and asking questions (in order to make my own mind up) is considered some kind of admission of guilt for being part of the "other". For example: Asking someone why they think immigration is good/bad. If it's a belief they hold, I'm interested in knowing the thought process and making my own conclusions based on something I might not have known. But the act of asking the question makes the person, who may not have put too much original thinking in; quite defensive.

It may be a matter of knowing when to stop. My personal experience is that most people will try to answer even sensitive questions when you approach them with genuine interest and make some effort to formulate questions in a way that doesn't imply some sort of value judgement. If this is difficult, just be explicit and explicitly say you're not trying to judge or offend them.

Sure enough, you'll hear people make an argument that you find unconvincing, or they may not answer the exact question that you asked, and some people will even admit they don't know why they believe something. When that happens, you'll have to accept that as their answer (and draw your own conclusions in silence).

People do get hostile when you keep "nagging" - asking more and more questions - when it's clear that they aren't interested in the subject or haven't thought about it much. To the other person it feels like you're either trying to make them feel stupid or change their mind. And you're getting none the wiser anyway because those who do not get offended will just make up their "reasons" on the spot.

Obviously avoid the mistake to ask someone for their opinion, and then immediately returning the "favor" by giving your opinion on the matter.

> Thinking for yourself is overrated as society is not built for it if you want to fit in.

I agree that if you want to fit in, thinking for yourself is counterproductive. But I also think society has more escape hatches for unconventionally minded people than it ever has, and if you don't care about fitting in the penalties have never been lower.

Find people you can be honest with and have those conversations. There aren’t many. Then sugarcoat for the narrow minded people. There are many.

> thus it requires strenuous effort to empathise

But does it? The strenuous effort part? Empathy doesn’t require strenuous effort, it can’t be that hard to relate to the core struggles of anyone you don’t know yet, surely you’d have to be some sort of magician to empathise at the granular level even with someone that looks like you (not sure how relevant that is but seems to be important to you), comes from the same school and now lives on the same block of flat as you do, as they could have gone through life having the complete adverse experience from yous, but at the core level, as long as you’re not some sort of social anosognostic, it’s not that hard to relate to what complete strangers from obscure environments feel/want/think like.

This is easily tested by simply taking a trip to some remote place you don’t speak the language and you’ll see how quickly empathy kicks in and how soon ‘conversations’ are happening where you totally relate to what they are going through perhaps not as much as they can relate to what you’re going through you lunatic explorer of the subconscious. Then with time as you learn their language, well, fuck it, as long as you are wearing some shade of grey you will fit right in where you are right now and wear your mask.

> it can’t be that hard to relate to the core struggles of anyone you don’t know yet,

The issue is more in the relating to struggle that you never went through and never observed. In order to relate, the other person would need to be unusually great at expression what it is like, what constrains they have and you would also have to be very good listener.

That is unlikely combination typically.

I think questioning someone's ideology or beliefs to their face has never and will never win them as a friend. These things generally aren't rationally founded anyway. If you ask about some political issue, you're going to get regurgitated talking points and tribalism, not a thesis. I think it's quite rare to meet someone willing to suspend belief for a bit and engage in unbiased debate, or at least I haven't met too many. This line of thinking can be helpful in a technical context though.

"Questioning someone's beliefs" doesn't have to mean "tell the idiot why I'm right and they're wrong in the form of a series of questions".

If you ask with sincere interest and an open mind, and avoid passing judgment on the answers you get (including with nonverbal cues), the person you're questioning will generally feel flattered, not attacked. This is how good journalists get people to open up to them.

If they aren’t “fastidious about truth” probably. If they are, and they know you are being “curious”, you will likely have a cool, engaging conversation on your hands.

> But the act of asking the question makes the person, who may not have put too much original thinking in; quite defensive.

Honestly, this is a good thing. Don't talk to these people. Over time I've found friends that I can discuss rationally with about many of their disparate experiences, them being from various races, genders, nationalities, and other such factors.

there's a degree of social intelligence involved with your examples. It's not really about "thinking for yourself", as everything is about context. uou don't have to completely become the other person in order to empathize. For most people it does not require strenous effort.

evolution is all about the ability to fit in. this includes the ability to be your own person with your own opinions. a well adapted person can do that and still being a part of the group/society

> However I'm now in situations where the world is divided and asking questions (in order to make my own mind up) is considered some kind of admission of guilt for being part of the "other".

I think this is partly because the rules or conventions that allowed rational discussion in good faith have been hacked by those acting in bad faith. The sad truth is that good faith discussion has been utterly rhetorically hijacked by things like "just asking questions" so when someone is genuinely asking questions you are assumed to be acting in bad faith. I have no idea what the answer to that is other than to find people you can trust to have these conversations with. And the danger is a lot of the people you think you can trust are just more people acting in bad faith.