My first recollection of having a "conversation" on a computer was ~1984. It was a text-based game on the Apple II that I can't remember the name of, but at some point in the game you could end up in a church or temple, and you could ask it anything. Of course, the game was limited in the number of different answers it could give at random, but the answers were all general and sagacious enough that they could be interpreted as some kind of meaningful response (at least to a 12 y/o). Wish I could recall the name of the game. Anyone?
@briankrebs Sounds like The Prisoner. It had a section like that, where you, number 6, had to not give up some information to your captors. Based off of the weird and wild British TV show of the same name.
@simplenomad @briankrebs +1. The Prisoner.