I remember doing this sort of things almost thirty years ago on the UI-Champaign PLATO system. We were much less intense - it was more like a Turing test. A guy would represent himself as a girl and see how things went. Interesting stuff...SSZ
PLATO? Hey I typed my French homework on PLATO in the Foreign Language building (right near those really stinky ginko trees).
I also remember using the UI-Champaign PLATO system. Never used it for picking up girls though!!
Hard to believe how far we've come (and in some ways, how far we've regressed!)