"weird" isn't a good description. Specifically, most people on the internet back then were well-educated computer nerds, so the typical post would be more relatable to those on HN and arguably (according to those on HN) "higher quality".

These people aren't "weird" in a bad way, but in a "different than the average (less-educated, less tech-oriented) person" way.

The anonymity part probably isn't correct. But I get the impression people back then were a lot more open, at least hearing about dating sites, chat-roulette, old YouTube channels, and internet friends who met IRL in the 90s/2000s. Although I know a lot of people post on Facebook and Twitter, so maybe that hasn't changed either.