1. My experience is that, on an interpersonal level, left-leaning and right-leaning people who have an honest, intimate and open friendship can come to understand each others’ position quite easily over time. Why? Because they build trust through friendship, and the politics are secondary.
2. It might be fairly easy to say that, the dumber and more ignorant two people are — and the more extreme their opposing political positions — the more challenging it will be for them to come to fruitful insight of each other’s POV. But, more importantly, if they already feel hostile and alienated towards each other, and are isolated from each other in terms of any interpersonal connection or shared experience, it might be pretty impossible for them to bridge the distance between their positions…ever.
3. Empathy is a powerful perceiver and communicator. If folks of opposing views have “strong empathy muscles,” they probably can achieve a basic understanding of each other’s perspectives with some concerted effort.
4. With all of these caveats, I would still have to say that I encounter more people with what we might call “identical, lockstep, reflexively regurgitated groupthink” on the right-leaning end of the spectrum than on the left-leaning end — and part of that groupthink is to deliberately distort and misunderstand left-leaning positions. That is not to say this same phenomenon doesn’t exist on the Left…it does…it’s just a lot more rare.
We can see a parallel example in media: if you compare the extreme bias and low factuality (or conspiracy-mongering) of media outlets on a site like Media Bias/Fact Check - Search and Learn the Bias of News Media (http://mediabiasfactcheck.com), the ratio of really “out there” right-wing media outlets to left-wing ones is about 10 to 1. That is, there are roughly ten times the number of right-wing media sources that are basically promoting yellow journalism, counterfactual reporting and conspiracy propaganda. In my experience, that’s about the same ratio of right-wing folks who can’t understand the other side vs. left-wing folks who can’t understand the other side.
My 2 cents.
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