[handoflixue]

> always ending in a similar deadlock where they just stop replying, either because they're sick of me, or I've "won"

My general experience on Hacker News is that threads rarely go beyond one or two replies, so I'll often tap out on the assumption that the other party isn't likely to actually read/respond to any thread more than a couple days old. As far as I know, there's not any indicator when someone replies to your comments, unless you go and check manually?

If I'm just using the site wrong, do please let me know!

Otherwise, I'd suggest you might want to update from "sick of me" to "never saw the reply due to the format of the site". For what it's worth, it took me a while to adjust to that

[yencabulator]

See e.g. https://www.hnreplies.com/