Bored? Have a webcam? Not bothered by Freak?

Then Chatroulette could be for you!

New York Times: The Surreal World of Chatroulette

Nothing can really prepare you for the latest online phenomenon, Chatroulette.

The social Web site, created just three months ago by a 17-year-old Russian named Andrey Ternovskiy, drops you into an unnerving world where you are connected through webcams to a random, fathomless succession of strangers from across the globe.

[...]

Before you rush off to your computer to try Chatroulette, it is only fair to let you know what you’re getting into. Entering Chatroulette is akin to speed-dating tens of thousands of perfect strangers — some clothed, some not.

[...]

In its simplest form, the site does exactly what its name says — it pulls you into a game of roulette. I used the service for the first time a few weeks ago, and I found it both enthralling and distasteful, yet I kept going back for more.

What to make of chatroulette?

"how did it take 15 years for the Internet to deliver this experience?"

NY Mag: The Human Shuffle

ChatRoulette is, in this sense, a blast from the Internet past. It’s the anti-Facebook, pure social-media shuffle. It arrived quietly last November, with no fanfare.

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Sounds like the old days of Skype or the scene from (I think) Heinlein's Friday whereby the rich look for dates via hologram.