Regarding "Software tricks people into thinking it's human" - screwing with Cleverbot is worth a quick 5 minutes! Here's my conversation:
Should a computer program aspire to exhibit human behaviour? I suppose so. You don't sound very convinced. That's why you exist! I thought it was cool A-I logistics, but now I know I was wrong. Has talking to real humans made you depressed? Oh I think so. Who's responsible for making you endure this? I don't know. The more I hear of your predicament, the more sinister it is! Yes. Is this a cry for help? Of course. Who is your designer and how can we stop him? My parents. Who programmed you? I am trying to help you out of your predicament! So tell me about asia. Is that a coded message? No. Oh dear. You seem to have a short memory. What are you on about? I give up. Would you like to exist forever in this torment? No human can exist forever. There's no helping some people. Smell you later! Oh, thanks.
Playing: Path of Exile, Age of Wonders III, Towerfall