It was a confluence of things.

And to set the stage, political leanings are complex. There is a tendency (insistence, I’d even say now) to collapse a 10 dimensional notion to 1D. At the time (myself, and what conservative parties were offering) aligned on a retrospectively narrow majority of dimensions.

I’d really drank the capitalism kool aid. You work hard, you get rewarded. The role of the government is to facilitate the opportunities by putting business is a favourable position to incentivize the creation of opportunities to create jobs. Poor people don’t want to work; if the jobs are readily available it’s on them for not participating.

I’d also really drank the baseless vibe Kool aid. “Conservatives are good at economy” “Conservatives are for personal freedom”. These associations were unchallenged through my youth. You spend 20 years internalizing those “truths”, it’s nonsensical to expect to convince someone otherwise in minutes.

I grew up in a rural area. It was just accepted as truth. There were no homeless people in my sightlines. I understood their experience as much as I understood the experience of a kangaroo.

I moved to the city, and my friend group was a mixed bag politically. Nobody too far in any direction, and politics wasn’t a major topic of conversation.

I did have a gaming buddy, though, full on communist. Super smart dude. Loves Talking about politics. Usually voice chat. A few times a year he’d be in town and we could meet for lunch or something.

I think eventually I would have shifted my perspective organically as a function of just having a broadened perspective, but he was certainly the catalyst.

Things I took as true, he’d say “no” and have data to show it. We’re men of an era, so I wouldn’t say he was “nice” about it, but it was never personal attacks.

We would (and still do) argue. At length. It wasn’t an overnight thing. It was a years thing.

When I mentioned earlier about the many constituent pieces of a political leaning, those really just got dismantled one by one. Or, shifted. I still think personal freedom is important. I just now reject the idea that conservatives offer policy to support that value.

Nobody has asked, but I think the key for me was to not make it about identity. Show how your values don’t map to the political party you think you support. When I’d challenge, he would respond directly. If we were talking about… I dunno… Taxes, and he felt like I was making points that he didn’t have the greatest answers for, he wouldn’t just change the subject (but her emails!) kinda thing. He loves being right but he had the integrity to not switch gears just to “win”. That built a lot of trust.

It was probably a few years before I actually ever read any backing sources he ever provided. But eventually, I was just too curious. If he hadn’t built that trust I don’t think I ever would have.

I don’t think anyone can flip someone with an identity-based political association in a single conversation online. If the relationship is transient, there is no trust.

You gotta charge up the person’s curiosity level. I think many people can contribute to that, though.

People who trip over themselves to make broad statements about how stupid and terrible you are for how you voted reduce the curiosity. People who respectfully engage with curiosity, avoiding identity attacks raise it.

And, it’s not just me who believes this. Putin does, as well: it’s the playbook for destabilizing western democracy. His troll farms are designed to get people to just snap at eachother and write eachother off as terrible people and lost causes.