What is the strangest online interaction you ever had?

I was in a roleplaying channel on IRC many years ago, and during a huge netsplit, events from 45 minutes earlier started playing out: same people joining, same messages being sent, etc. but with most of us still in the room observing. We had a unique opportunity to roleplay with ourselves and remix what had transpired before.

I used to sell platinum (in-game currency) and items on a private Everquest server for the equivalent value in dollars.

the interactions I had with the farmers who sold to me, server staff which were working against me, and the buyers of my goods were probably some of the most memorable i've ever had online.

http://rationalwiki.org/wiki/Dennis_Markuze

I knew he was a nutter but never realized how far it had gone until I happened on the article. Guy harassed me for months.

This guy is still (sorta) after one of my coworkers. Apparently the direct threat of jail isn't working so well.