When talking with libertarians you should keep in mind they have completely different axiomatic values. It is often the case that they understand a certain policy would be on net bad for everyone, they simply don't care. They are rarely utilitarian about those issues.

I get along much better with libertarians who justify libertarianism with values extrinsic to just "muh freedom" -- they are usually much more willing to yield ground in places where I can convince them that a libertarian policy would be net negative, and they have also moved me to be more open minded about some things I thought I would never agree with.