Up front, I've been drinking which doesn't help my rhetorical skills and got into it with my lib friend about Ukraine et al. It was a long conversation that ultimately went around in circles, but the jist of it was that on my end, we should not endlessly prop up the meat grinder of Ukraine as it serves nothing but the western imperialist project. On his end, the argument was that Putin is a maniac and that nato should not appease him in his crusade to restore the Soviet Union. He came from an upbringing of UK champagne socialists and seems to have settle on lib nihilism as his pathway through life.
I'm not sure what I'm seeking from this post, but I guess, how do you all deal with the conflict of people that you love desperately clinging to the horrid power structures that replicate the horror of the modern world? I've been pretty blasé about the results of the US election, because the dictatorship of the bourgeoisie will continue on its course regardless, but it's really hurt that someone I care about deeply has taken the "you're a tankie, you must love le pootin" position against me. 
I hate that wanting something better for humanity is the madness rune. I guess I'm just deeply sad, and I love you all so much because without all of you here I would only be left thinking that I must be mad for hoping for something better.
Debate is a lot less effective than you'd think. Poke holes in their arguments and get them to look things up on their own time, you're not going to be able to convince someone who is just ranting at you.
I try to not make a habit of debating, because the results are usually the same. I was taken off guard because we'd never talked about the subject before and I didn't expect the usual western propaganda line from him.