It’s about finding joy in randomness.
For most users of all ages – but especially teens – the Internet today is about socializing with people you already know. But I used to love the randomness of the Internet. I can’t tell you how formative it was for me to grow up talking to all sorts of random people online. So I feel pretty depressed every time I watch people flip out about the dangers of talking to strangers. Strangers helped me become who I was. Strangers taught me about a different world than what I knew in my small town. Strangers allowed me to see from a different perspective. Strangers introduced me to academia, gender theory, Ivy League colleges, the politics of war, etc.
I completely agree, ChatRoulette feels like my first experiences meeting random people in AOL chat rooms. But I can also understand why many people would find it too creepy to try out.
There’s an iPhone app called PhotoSwap that operates on a similar principle. It’s also fun, but it’s too bogged down by those who tag their suggestive, but PG-rated, images “NR” for no reporting to the system administrators.