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In my experience you've got two different categories of productive arguments with those of a sufficiently differing political alignment.
You know the person reasonably well, have an established relationship that they value and they have some respect for you
You have no strong links to the person you're arguing with and there are less ideologically committed onlookers
In the first situation I've generally had success by being assertive about what I believe to be true, giving the reasons for why I hold said beliefs and generally emphasising my good intentions. Your mileage may vary however. I don't attempt to "convert" people I've got good relationships with, just respectfully disagree when they say something I feel to be particularly egregious. My strong/assertive personality also probably colours all these relationships and influences how these things go. Or maybe I'm just lucky and happen to only have relationships with reasonable people.
In the second case I opt for a different tack. You have no chance of bringing the other person round to your point of view by being reasonable, so instead your aim should be to dominate the discussion with the aim of influencing the wider community. You're a stand up playing to the crowd, with the aim of making your opponents ideas look ridiculous and yours reasonable and sensible. This requires quite a bit of nuance, a general feeling for the crowd and a quick wit. There are a number of benefits of this kind of strategy compared to the usual kind that I see posted here (hide your true convictions, scuttle around in the dark trading essays with like-minded individuals on how everything has just gone so terribly wrong), this is very much a case of planting a standard. There are downsides to planting a standard, it makes you a target and people know your alignment, but there are also upsides. People know your alignment, like minded people may come to you and I think most importantly, it gives whatever you believe in a degree of legitimacy. It shows that yes, people do believe in/support whatever your standard represents and that they will absolutely sally out to defend it. Your average person is incredibly averse to confrontation or being singled out and will generally modify their behaviour to avoid it. Not everyone expressing woke viewpoints is a committed antifa supersoldier, most have just absorbed these opinions via osmosis.
It's also worth mentioning that obviously walking directly into google and loudly declaring "I think one holocaust was simply not enough" is a great example of how this line of attack does not work for every situation or argument. If your beliefs are so unpopular that you can't declare them openly without very serious consequences (I would firstly urge you to consider if there is perhaps a reason for this and if it might be possible that you are the one with the cooky beliefs), I would say that your best bet is to read Maos little red book and generally brush up on your insurgecy/counter-insurgecy literature. Obviously these are great tools for fighting an armed struggle against a powerful adversary, but the wisdom contained within also applies to un-armed conflict between two (initially) unbalanced forces.
I've gone off on something of a tangent with this post, it's somewhat evolved into a rant about my dissatisfaction with the doom posting and general passivity I tend to see advanced around here.
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