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For example, I like a web game called the Kingdom of Loathing, their chat channel has the usual silliness, good gameplay advice, and general random conversation. As the OP states, getting into a chatroom in AOL was as simple as a couple of clicks.I have no idea where I could do this now, even though I have often heard or read about Internet chat rooms.
Or hit up Second Life which *is* mainly a chatroom with graphics.
Yahoo has (or had) chat rooms available through their Messenger.
I used to use one often when they allowed private rooms to be created (there was one for Denver gay men).
I've chatted with Dopers on two different media, although both revolve around specific games...
We use AIM to chat while we play our SDMB poker games on Thursday nights....is our current thread for the quarter.
We do have a Doper Guild in World of Warcraft.....sometimes we get on Ventrilo to chat or ideas to defeat Bosses in a raid....although we haven't been using it lately because most of us are waiting for Mists of Pandera to come out, I think we will be using it again pretty soon.