Describe, or better yet, relate verbatim the funniest, weirdest, outrageous or otherwise remarkable dialogues from chat rooms that you’ve seen -- bad spelling and all.

Unfortunately, I don’t spend much time in chat rooms and I’ve written this in an answer before, but my buddy @lucillelucillelucille wrote this in a PM to me once: “Googles? I now have proff that I spend too much tiome on th ecomputer!LMAO!”
Exactly like that. Typos and all. I barely have any idea what she said, but I think it’s funny as shit. XD

I don’t have anything saved on here, but it’s always on chatroulette.com or omegle.com
I’ll try and describe it:
Stranger: Hey saxy gurll, cum?

Costello: Well then who’s on first?

Abbott: Yes.

Costello: I mean the fellow’s name.

Abbott: Who.

Costello: The guy on first.

Abbott: Who.

Costello: The first baseman.

Abbott: Who.

Costello: The guy playing…

Abbott: Who is on first!

Costello: I’m asking YOU who’s on first.

@ChazMaz , hahahahhaha i crackeeedddd!

On chatroulette this random guy from Arizona was dressed as a ninja and showing off his karate skillz. We had an awesome conversation about random stuff. All while he was shadow fighting.

@Mtl_zack , chatroulette is awesome for some strangeness! and randomness!

I don’t frequent chat rooms, but…once, about 8 years ago I participated in a chat thing.

One night this guy solicited me for some ‘role playing.’ lol

Think I handled it brilliantly. :-)

Me: So what do you want to play?

He: How about Boss & Secretary

Me: Okay, I’ll be the boss.

He: Uh, but I’m the boss.

Me: If I can’t be the boss then I don’t want to play.

He: But. but…

Me: Oh Mr. Secretary…please bring me my coffee!

He: dead silence, disappeared.

lololol

NSFW.
The Exploits of Bloodninja

I thought (NSFW) this was pretty funny. In a disturbing sort of way.