I wanted to see just how far I could get into an awkward conversation on the anonymous chat website, Omegle. The answer is... Not very far.

First fail. Of many.

Getting closer...

They can only take so much.

Well, that's about enough fun for tonight, folks. I have to go. Someone is knocking on my door REAL hard. It might be an emergency or something.

We know you love it, so here is another Omegle post!  Hot Troll on Troll action!  Our responses are the absurd ones in blue text!

Sometimes I wish there were time stamps on Omegle.  The chat below lasted about 20 minutes and it was a very one sided conversation. Each of my comments were about 2 minutes apart.  Sometimes patience doesn't pay off.

This is a different kind of Omegle conversation.  A third person submits a question and watches 2 other people answer/debate it. 

 This was my favorite one of the night.  Knocked that fucker out of the park!

It said that the other person was typing the entire time, but they never gave me a response.  I really wanted to know what they'd prefer.

It's that time again, when we take to the internets to abuse and disgust strangers on Omegle! So without further ado, I present you with our most recent awkward online conversations. And as always, our responses are the absurd ones in green text!

That went well. I'm pretty sure this was either an incredibly sad obese man or a bot. Here's hoping for the former!

I must admit I didn't expect to get a willing buyer so fast. Now I have this baby all boxed up and waiting for an address to send it to.

God damn it! This guy is probably using a pic of this conversation to leverage his own meaningless and unsatisfying internet fame! No fucking fair, asshole!

Nothing like a manufactured crisis to bring out the best in the online community. Now I need to secure a good lawyer, just to be safe.

I tried. I got drunk and went on omegle in pursuit of hilarious conversations with the mix of pedophiles, date rapists, and overall depressing bastards. But alas, I had very few people willing to play ball with me and ended up just scaring away several people. Maybe next time I will pretend to be a 16 year old girl and count the skype requests. As always, the green text represents my end of the conversation, as if that weren't obvious by what was written.

Just another drunken romp through the anonymous chat services on the internet. As always, my responses are in green. First I decided to test the boundaries of decency by challenging a stranger's threshold for offensive commentary. Always a good ice breaker.

Ok. That was a decent start. Next I decided to engage the strangers in a bit of role playing, where I offered some creative punishments for their personal enemies.

So that went... Pretty well I guess. At least I am getting some participation from the online community of lonely drunkards and shut-ins. Finally I got a little vigilante streak and called out a probable internet liar by demanding contextual responses in real time. The results were satisfying.

There you have it, folks. Another hastily and lazily produced post of improvisational comedy with strangers. Hope to see you online! Oh yea, if you do frequent these sites, never start a conversation with "asl" because it makes you seem like a pedophile trolling for children to harass. Unless you ARE such a pedophile, in which case proceed, I guess.

Every once in a while we decide to make some friends on the interwebs, but sometimes it is difficult to establish a genuine human connection. Here are a few failed conversations that demonstrate this problem. As always, we are represented by the green text.