I remember one conversation in particular that, by chance, went so well that it had some poor soul convinced it/she lived in his city and was going to come over.
I also saw a TV episode where a magician demonstrated supposed ability to play simultaneous (round-robin) chess games against multiple grand masters. The conceit behind the trick was that (after the first board) the magician was just mirroring the last move made so that the grand masters were effectively playing each other but didn't know it. That gave me the idea to modify the bot to connect two people through the bot.