I’d suggesting trying a debate tree containing only the best, most important arguments (or decisive only if the friends are open to that). Just getting a curated, organized visualization helps a lot compared to most typical debate situations.
That’s hard. I’ve had little access to debate since I developed CF. This is partly due to the harassment campaign, partly due to the rise of social media, but I think mostly due to raising my standards, knowing more (it’s harder for people to say useful things that I don’t already know), and changing how I debate compared to years earlier. Changes include bringing up methodology and prerequisites more and putting more effort into keeping things clear and organized.
Here are two of my most recent long debates but I think they aren’t very good due to flaws in the other party (who, among other things, didn’t know or try to follow CF principles):
This is the only person from the Effective Altruism I could get to talk much. Things began when I went to their forum and asked “Is there a way here to get organized, rational debate following written methodology?” I think the answer was there’s no reasonable way to get debate from EA. EA also didn’t engage with critical articles.
This has a large debate tree made by me in the middle by memory and is after I was using an explicit debate policy. One of the lessons from this debate is that people can agree to debate terms/rules that govern e.g. how the debate may end and then simply break their word.
I don’t know what debates would be a good exercise to analyze. It depends. Maybe much shorter ones. I don’t know of any particularly high quality, productive, rational debates between public intellectuals, especially not the sort of debate that uses quotations heavily and has many back-and-forth exchanges.