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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.
Good advice. Thanks! I will try reframing some of my questions a little better.
Honestly, it will be tough with him. He's incredibly naive and not terribly introspective, but if I can find those points of agreement, perhaps he'll be a little less defensive on the outset. Doesn't help that my sister and the rest of the family are all liberal and leftward, so he's an island.