I miss random synchronous chats with strangers, but I think I liked them because the stranger pool was a lot less creepy. I'm not sure I would enjoy them now.
FWIW, someone I met doing random AOL profile searches in the mid-'90s and I are still online friends. We both liked the Dave Matthews Band and played varsity tennis, and this met my minimum chat requirements. Now we are both former journalists working online, dealing with bipolar disorder and the recent death of a parent. The internet might be weird sometimes, but that (and a random story of getting a web development job because someone had the wrong email address for the person they were actually trying to hire) will always go down in my "Internet wins" column.
I miss it in a nostalgic way too. Obviously we’re all >20 years older now and I don’t think I’d even have the time for it (I barely have time to read HN most days.) But yeah, the fact that most normal people online were doing it then meant you could really connect around shared interests. Nowadays, I assume if you’re talking to strangers you’re a weirdo or looking for something creepy because “A/S/L?” was creepy. Part of the reason I feel the internet is safer for kids these days, they’re only talking with real life friends for the most part or engaged in a voyeuristic behavior (celebs, influencers, etc)
FWIW, I have a couple friends like that. We bonded over some musical interests of our teens and occasionally check in on each other although most never met in real life. Maybe that’s still happening in game chat? But I can’t imagine something like yahoo chatrooms still exists.
FWIW, someone I met doing random AOL profile searches in the mid-'90s and I are still online friends. We both liked the Dave Matthews Band and played varsity tennis, and this met my minimum chat requirements. Now we are both former journalists working online, dealing with bipolar disorder and the recent death of a parent. The internet might be weird sometimes, but that (and a random story of getting a web development job because someone had the wrong email address for the person they were actually trying to hire) will always go down in my "Internet wins" column.