Great post! I’d never heard of Britewiremedia or Generatus, but I’ll definitely try them out.

However, I had heard of Omegle. I love Omegle, but I wanted to be able to access it using my favorite chat software (iChat and Gmail). So I wrote my own “chat with strangers” webapp, and I thought I’d tell you about it. You may find it interesting, as it seems to fit the theme of your post – minimal, quirky, and hopefully fun. :-)

My app is called Social Butterfly. It allows you to anonymously chat with random strangers over Google Talk (if you have Gmail, you already have Google Talk). You can use it with your favorite IM client, even on your mobile device.

If it sounds interesting to you, try it out here:
http://social-butterfly.appspot.com/

Thanks, and keep up the great blogging!