Random chat room
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Created by a Russian school boy, Chatroulette connects millions of strangers in random video conversations.
The web app itself is pretty bare-bones, with two video panes showing the user & you, a huge pane for text chat and a couple of buttons for controlling the chat.
anybodyoutthere is a random chat service with an awesome UI and concept.
You can ask a question or share a thought and you will be shown a list of people with similar interests to talk to.
Additional side, there are many random free chatrooms for chatting sites especially for teen chatting where one can get countless online strangers all the time along with private chat rooms. Almost all of the chat random sites randomly pick the people from all of worldwide.