I think questioning someone's ideology or beliefs to their face has never and will never win them as a friend. These things generally aren't rationally founded anyway. If you ask about some political issue, you're going to get regurgitated talking points and tribalism, not a thesis. I think it's quite rare to meet someone willing to suspend belief for a bit and engage in unbiased debate, or at least I haven't met too many. This line of thinking can be helpful in a technical context though.