How easy is it to have a conversation with a chatbot and not realize it?

Asked on Quora and answered by George Huestis here.

During a stint of internet dating I once had a conversation with a pretty girl who I assumed was a bot because she was, as near as I could tell, unable to comprehend sentences.

I tested this hypothesis by making my sentences more and more nonsensical (using imaginary words and the like) to see if she would a) say “wtf are you on?” or b) ask for my phone number (jump the shark - bot!).

She asked for my phone number.

I said: “No thanks, for [these reasons] I think you’re probably a bot trying to harvest my personal information.”

… later, for various and sundry reasons, I figured out that she was real.

An actual, honest-to-God human.

… she just failed the Turing test.

So probably it’s pretty easy, but not because the bots are so good at pretending to be human.