I don’t have any specific advice, but generally when trying to convince people of things it’s important to remember that belief is largely social. Facts don’t matter so much as group identity. We are all vulnerable to this. If they see you in the moment as being in an out-group, you’re extremely unlikely to convince them of anything. If you can focus on shared group membership, like “we both want to see our kids grow up healthy” or whatever, that can work.

Like, if you try to convince a conservative to recycle via “it’s good for the environment” that’s going to ping as outgroup nonsense. If you sell it as “only america can turn trash into useful stuff”, you’ll probably have better luck.

The Trump-loving libertarians are a weird batch. Typically the trumpanzees I deal with are GOP, and my strategy is to actually talk up the LP in an attempt to use Chase Oliver as more benign trash can to drop would-be Trump votes into.

For actual libertarians who are already planning on voting Oliver, I point out that a fascist victory would be fatally damaging to every party except the fascists - 3rds are fucked right along with everyone else. Their best strategy is to nudge the current system into a model more conducive to a 3rd party victory, specifically via ranked choice voting so people can feel safe voting for a 3rd without worrying about the spoiler effect. To do that, they need to vote blue to keep the fascists out of power, as a vote for more time to refine their party of preference and preserve a political model that could lead to that party’s victory.

Trump LPers are harder to speak to, to the point of being a lost cause in most cases, but I can understand wanting to give a little extra to help out a family member. Start digging into policy questions - less who he wants to win, and more what he wants to accomplish. Assess those goals, and consider if someone other than Trump would be better to achieve them.

This debate technique is called “steelmanning” and requires putting yourself in the other side’s shoes, and building their side up in a way that’s compatible with yours, vs the usual talking points nowadays, which are usually just strawman bullshit that will never get anything done.

Good luck!

Vet here, also former libertarian, current father.

People smell bullshit, so ask genuine questions. If you have an agenda it wont work.

Ask about what kind of role he sees for government, and ask about situations you find troubling and what he things the solution is.

Ask about specific people you may know who are too underprivileged, young, old, infirm to be self sufficient and bootstrap themselves.

Generally give real thought to your opinions and ask him about his. You really can’t change people by wanting to do it, you have to want to understand them first and then enter into dialogue.