I'll admit it: I miss anonymous chatrooms.
Let me explain. They do still exist (obviously) and a lot of the time, AIM chatrooms were really skeevy and gross (do we need to explain why “To Catch a Predator” became a thing? Do we?), but there's still something I miss about it.
For a while back in high school, I used to frequent live-streams of horror movies (and “The Room”, but that's a different kind of horror movie), and you didn't need to create an account if you wanted to participate in the discussion of the stream-chat. Even with the pseudonymous usernames, there was still a sense of anonymity in the chat. This was a period of time where on /x/, 4chan's paranormal board, you could still announce that you were hosting a livestream, and there were some of us who gathered to watch mostly bad scary movies and laugh at them.
I think they probably stopped allowing live-streams because there were people who would film themselves playing the Midnight Game, which involves blood, and that kind of went against board rules, but I digress
Most people at this point had dropped off from AIM (AOL apparently never really supported the messenger service in the first place, which sounds surprising given the fact that by the mid 2000's, that what most people my age recognized them for). There was Omegle—still is, in fact—but it wasn't really the same because you can't expect to talk to the same people every time you start a new Omegle chat in the same way you can if you were to go to a live-stream chat or AIM chatroom, or anything else of that ilk: Omegle is anonymous in a different way than AIM was anonymous.
Of course, it's not really a thing that can exist in the way it used to anymore: For one thing, more and more of our lives are increasingly online as opposed to “in real life,” and for another, you can't go to any website without being asked if you want to broadcast your association with it on Facebook, Twitter, and even Google+. This can be seen as both a good and bad thing. We both want our friends to know what we're into so if they like it too, we can hopefully talk about it, while at the same time there are some things that we might actively dislike the idea of anyone who knows us from school or work to know that we really like, I don't know, fan-fiction, for example.
I met two of my best friends through the live-stream chat. It's interesting to think about: You don't know what this person looks like, whether they are who they say they are behind the screen, or what kind of front they're putting on. After maybe a year of talking in chat we ended up being friends on Facebook (and did, weirdly enough, have a mutual friend in common—it's a really small world, I've found), and we still talk (thought not as frequently as we did back in high school).
You might not know who you're talking to, which most critics of the online universe say is dangerous—and it is—but that's not necessarily a bad thing. I'd rather make friends with someone after talking to them than by seeing them first, I think, because at least then you don't have the societal pressure of only having to talk to a specific group of people.
Coming of age with the Internet when Web 2.0 was exciting and strange and those chatrooms probably helped a lot of people who might not have known who they were come into their own and figure out what they were and, more importantly, what they won't.
And sometimes, I miss the kinds of conversations you could have with a person if you didn't have to worry about looking them in the face the next day.