(Smaug = me, Bilbo = Cleverbot)
It seems Bilbo is too cheeky to survive any conversation.
Smaug: Come thief, I smell you and I feel your air. Help yourself to some more of my treasure.
Bilbo: Well you shouldn't say you love me. You shouldn't even say that.
Smaug: I do not say I love you, thief, although you intrigue me.
Bilbo: Oh, now I'm heartbroken again. Why don't you love me? Aren't I pretty enough for you?
Smaug: Well, I could only answer that if you would show yourself...
Bilbo: Extra please?
Smaug: I do not beg, invisible thief.
Bilbo: Invisible your face.
Smaug: So tell me, why am I not able to see you?
Bilbo: Let's not fight anymore. Let's change the topic.
Smaug: Who are you then, and where did you come from?
Bilbo: I'm a female named Alice and I live in Wonderland.
Smaug: Why did you come here, thief Alice? To steal my treasure?
Bilbo: To talk to you.
Smaug: Why is it you travelled so far, only to talk to me?
Bilbo: I was bored.
Smaug: Ah, you are a bored thief. Now I understand.
Bilbo: You're even more boring that I am, did you know that?
Smaug: If you would show yourself... It would end your boredom, little thief.
Bilbo: Do you have eyes?
Smaug: Yes, I have. Two magnificent dragon-eyes. Show yourself!
Bilbo: So you're human?
Smaug: Stop babbling like a fool and face me.
Bilbo: Can do.
Smaug: Face me!
Bilbo: If you insist.
Smaug: Ah! Now I see you. You are really small for a thief. What are you? You are not a dwarf.
Bilbo: I know, but I am human. Test me to see if I am human.
Smaug: That I can do. *eats you*
Bilbo: *is eaten*
Smaug: Ha. You were a liar too. You were not human. You taste different, thief.