I learned, and am still learning, to start with very subtle conversations in contextual proximity to the person without shocking/surprising them. And then, I mostly try to listen more and try to guide them to talk more. You will be surprised at how many a lot are eager to talk to someone, if they are being listented to.
I don't mind small talk sometimes but there has to be some kind of common ground. For example with conservative family-first suit types I have nothing to talk about and it feels awkward to make conversation, but with the leather/mesh/blue hair alt/goth types I can talk for hors.
"hey man, how're the kids?" "Is your wife recovering from [illness] you mentioned last week?" "man, have heard the music on the radio lately?" "what kind of music do you like?" "can I ask you a personal question, what was the hardest part of getting the success you have?" "did you know you wanted to be a boss/manager when you were a kid? No? Oh, you wanted to be an astronaut? Oh man, no way, have you seen the crazy stuff spacex is doing with re-useable rockets? We're getting so close to (relevant sci-fi from when he was a kid)"
You've just got to have an open mind, which you'd think you'd have given your conversational partner preferences.
I am only partly paraphrasing actual conversation with my father in-law.
I cannot stress enough that what you think will work here doesn't: literally every topic will be pivoted towards a rant about which groups are destroying the future (all of them), or how it's all a conspiracy or how they are plotting against you.
You've invented a conversation you think works. I have lived a damn decade of the list of "safe" topics endlessly shrinking, and the punchline is same: 30 damn minutes of alternately being told some half remembered conspiracy theory from Facebook or asking for agreement that group are bad.
That scifi concept from when they were kid? Well they are lying about that for money of course.
It is exhausting to deal with over and over again.
But you're painting two different pictures as if they are the same. The suited family type and the conspiracy theorist are different people.
Were I to know that I were dealing with a conspiracy theorist, the pivot is "I wish I could pay as little tax as rich people do (knowing fully well that they often pay far more than I do" or "yeah, it's crazy how the rich always abuse the little guy" or "what would you do if you were in their position (the same? ah well, at least it's understandable. Different, there, you see, there are good people like you and I left to fight the fight!) Or, hell, just for funsies you can play Conspiracy Olympics in which you try to outgun and outthink their own wild ideas. "Oh yeah, well 'spacex is a fraud' is exactly what a russian sleeper agent would say!"
I'll admit that there have been a small number of people that I simply could not connect with on any level, but working in non-profits and with volunteers, you get used to people's quirks and figure out how to work with them on their level. And what's more, you'll often end up being considered one of their few friends or even just "one of the good ones in their book" because so many people are just completely dismissive of them because they don't like their ideas.
You're engaging in exactly the kind of behavior that many of them complain about, their "no one cares, everyone's out to get me" mentality is only enforced by your "it is not possible for me to talk to or associate with these people". You are in fact one of the they that is plotting to remove this demographic from your own reality. It is not a stretch for them to imagine that you would prefer that they did not exist.
Kindness is not complicated.
There are fringe kooks at all edges of the spectrum and they are all tiring and boring.
But most guys on the train wearing a suit are just normal people who have to dress like that because their work requires it.
And the thing is a lot of MAGA people do want these things. Otherwise they wouldn't happen.
But yes part of the blame lies with me too. It is as you say very tiring.
I understand that being either loud and proud or even just unabashedly your own self can be trying at times. I know, by first hand experience (as a cis-ish passing transwoman if you squint), that embodying your own reality in public can be a difficult and damaging experience...
But it's just...necessary. Even on a completely selfish front, no one's going to accept me myself for who I am if I can't tell people who I am. And then there's the larger front that those who have come before me did some of the work to make my life easier, and that by my own work I can make the lives of those who come after me easier.
It's just...sad, you know? Like I know it's hard for us to keep banging our heads against the wall. It's hard to go out in public and recieve insult after insult. It is hard to visit an unfamiliar locale not knowing how we will be accepted. But we have to! Literally the only path to acceptance lies through exposure.
That's the real reason that I am so sociable. I know that the only way past the insults is past the insults. If I only ever hide in the closet...well, the closet isn't all that big is it? I believe that if I show up as myself in any and every interaction I can only have a positive effect. At worst, I find people so bigotted that they are beyond help, avoid them, and pray for those few. In the middle everyone lets me slide. At best, I find bigots who I can expose to reality as it is and help them to get over their fears and prejudices.
I have found through experience, that this reality is closer to the best of possible worlds I just described and far from the worst of the worlds I just described. I have been rewarded time and time again in my encounters, finding countless people that I am able to relieve of their fears and knowing that I have saved countless unknown queers from the vitriol that those I have helped would otherwise have spewed.
The suit guy probably has more interesting stories than you'd expect if you gave him thirty seconds.
I'm more comfortable among other outliers.
Also they feel really good due to the materials being very smooth. Latex in particular is really like a second skin.
I would never feel good in a business suit because it's not who I am. Even if the fabric wouldn't feel horrible I would still be miserable. They're all the same too, like a uniform.
That they like getting compliments from the people they interact with? That it makes them feel good about themselves and feel like it matches who they are?
That the suit feels good too them due to the materials being quality and expensive?
That they would never feel good in leather because it's not who they are? That even if the leather wasn't sweaty and sticky, they'd still feel horrible?
Both of y'all are doing the same shit. You're wearing what you want to wear because it feels good to you and it feels good to you because you get compliments on it and getting compliments on it means that you've been accepted by the group you wish to be accepted by.
The suit and the leather gimp suit are the same thing. The vest and the kapris are the same thing. The turtle neck and the neck tie are the same thing. They are all status symbols. They all say "I want to talk to people dressed like this" and probably "I don't want to talk to anyone who dresses like that"
But if a business suit matches who they are then I'm not really interested in them. Which is what I said in the first place. I really hate business and the kind of people that spew PR bullshit on LinkedIn for example.
But really a job where I'd have to wear one means a job working with business people and I would be very bad at that anyway.
For weddings I just don't go if it's too formal, though most of my friends are very polyamorous. If they even marry it's not a huge deal.
could ya try?