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My advice is pretty broad and doesn't regard for the vast, vast spectrum of potential circumstances and potential conversations that arise from our various relationships. So I can't possibly account for everything. But I am speaking most broadly to situations when you may know someone in an interpersonal level who is open and vocal about their support for this administration and what's happening right now. Maybe a coworker or family member or friend of a friend.
Just not someone you're already having open arguments with IE: not someone you will feel emotional or heated talking to.
If you're already having stressful fights with someone about politics, the chances of reaching them with questioning radically diminishes and sometimes you gotta cut your losses and move on if you can't make headway. This is particularly painful when it's family members, but I wouldn't torture myself to change people just because we share DNA configurations.
I also encourage this approach of questioning only if you're actually comfortable with some mild confrontation, because it WILL invite argument. It's entirely in your court if you let it become a 2-sided argument, otherwise, again the idea is to JUST plant a question. They can rant and rave and throw things for two hours after you ask the question, you're not involved anymore. You can leave. You can put your headphones on and close the door. Let them rage at themselves for being questioned.
If this is the pattern you expect, then just work in that system. Question, let them rant and rave, and move on. Make your EVERY interaction a calm, collected and pointed question about what's happening and how they feel about it. Then let it sit there. You're not trying to argue or you're going to get distracted. They are very good at distracting you by saying things you're going to feel outrage at with whataboutism, distractions and untruths, . People are very good at pushing other people's buttons: you're trying to do this, but in a different way. They're trying to make you mad so they have an excuse to blow up on you. You just want them to associate this topic (politics) with your question (Is it working? Are things great yet? Can you afford healthcare and groceries yet?"). You're not even a factor personally, you're just the messenger for the question.
We all need to understand that with conservatism broadly, we're never, ever going to win an argument. Ever.
Arguments are intellectual exercises where to sides make a case to each other, two sides exchange facts and perspectives and counterpoints. Conservatives do not care about this broadly, they don't care about anything past how they feel right now, and what they want right now. They are children. And like children, they can only be trained over time with repeated reinforcement and associative teaching. Reward them when they say something good, give them compliments to engage them and take their guards down (they REALLY want your acceptance but will never admit it) and then pivot and attack the one, single idea they can handle at a time, (again, how are things better for them, how is their life better, etc.) and don't get distracted.
What all this does is it creates imaginary arguments in their head. They will have shower-arguments with you in their heads all the time, trying to figure out what they can say to you to prove they're right... and they're really, really bad at your game, so they will come to you with some jackass dumbassery and you will calmly look them in the eye and ask the previous question again, forcing them to start over. Do this enough and you will train them to question their own ideas.