Change your measure for success.

You aren't likely to win anyone over in a brief 5 minute discussion with a stranger on the street. It's exceeding unlikely that you're going to take an anti-communist lib and have them walk away from a conversation with you an avowed communist.

What you can do is shift opinion, make people walk away with critical questions that they will then go on to examine in their own lives, and potentially form connections with people.

Try to arm yourself with ways to connect smaller or more narrow special interest politics with socialism, e.g. women's rights -> the status of women in the USSR, the work of Kristen Ghodsee (will require some reading obvs but if you can get one feminist to walk away with the book recommendation for Why Women Have Better Sex Under Socialism then *boom* you've just connected the socialist cause to a political concern which is central to a person and you've basically set someone on the path to radicalisation), environmentalism -> Cuba is consistently rated as being the only economy in the world which is sustainable by the WWF; if we truly care about the environment then we need the entire world to adopt the Cuban economic model, Islam -> have a discussion about the nature of the prohibition on riba and what implications this has for the economic issues we see in society such as a housing crisis and the spiralling cost of living (and ultimately the nature of the economic system itself), concerns over the fact that communism advocates for violent overthrow -> get them to consider the depth and breadth of the violence inherent to the current system and the opportunity costs related to a reformist or incrementalist approach which necessarily consigns millions upon millions of people to needless deprivation, destitution, and death while we sit around comfortably and tweak the dials of the current system while telling everyone else to wait their turn and demand that they give us a few more centuries until we somehow manage to get it right, etc. etc.

As for knuckleheads, you're going to encounter them. When someone tells you to move to Cuba I like to tell them "Why go to Cuba for socialism when I can bring about socialism at home?" which usually terrifies or horrifies people like this. You aren't going to win them over when they're at that point so don't even try. Don't chase after them. Don't spend an extra moment thinking about them. Just get your best retort in and focus on the higher priority people. Have a few ripostes in your arsenal and deploy them as required.

I'd definitely take a mass line approach to this. In short - unify the advanced, bring up the intermediate, and isolate the backwards.

Get the cohort with the most advanced politics on the same page, or at least work towards that outcome given the constraints that you're operating under. Raise the class consciousness in the intermediate in whatever way is most salient to them. Ignore the backwards types.

Last of all know that social anxiety is very often a particularly lopsided or unilateral perspective of a social engagement. You're likely focusing on only your own perceived deficits and perceived mistakes. When you engage in anything social, there's a whole other world of perspective that the other person or people bring, and it's very likely not nearly as critical nor as observant of you as you are of yourself. Try to find ways not to internalise things like negative responses and rejection. It's never going to be perfect and you're never going to have a 100% hit rate. Make your peace with that fundamental fact and find ways to move on from "losses" without letting it drag you down.

People have their preferences and beliefs, and that's okay.