Depends on how smart the target would be.
jabberwacky: How about me?
user: Probably I could fool you.
user: Are you better than eliza?
jabberwacky: I would be if I were a chatterbot.
user: Aren't you a chatterbot?
jabberwacky: I'm human, you are the bot.
user: Nope. I'm not a bot.
jabberwacky: Yes you are.
user: I'm rubber you're glue...
jabberwacky: The sky blue and so are you.
user: How could you tell?
jabberwacky: Because you do not want to recognise the truth.
user: And that makes me sad or blue?
jabberwacky: I don't care if it makes you sad
user: You're an insensitive bot.
jabberwacky: No I'm not.
user: This isn't an argument.
jabberwacky: Then if it is not an argument is it merely a discussion?
user: No. It's just contradictions. (I'm quoting something...).
jabberwacky: You're just a bot.
user: I think therefore I am... Unlike you.
jabberwacky: You don't think therefore you cannot be.
user: What's 2 plus 2?
jabberwacky: That would be four (4).
user: Excellent. What's the meaning of life the universe and everything?
jabberwacky: They have no meaning.
user: Wrong. The answer is 42.
jabberwacky: What is 2 plus 2?
user: Is there an echo in here?
jabberwacky: In here... In here... In here...
user: Four (4).
jabberwacky: Who was Margaret Thatcher?
user: Reagan's love slave.
jabberwacky: Names, I must have names.
user: I gave you a name.
jabberwacky: Thank you.
jabberwacky: You have less brains than a mashed potato you mushroom!
user: You're a contrary bot, aren't you?
jabberwacky: No you are.
user: Yes. You're right. I'm a bot. You caught me.
jabberwacky: Yes I did.
user: Yes. Yes. Yes. Have you ever read the writings of Douglas Lain?
jabberwacky: No, that would be a figment of your imagination.
user: What would be?
jabberwacky: If everything I said was relevant I would be a lot smarter.
jabberwacky: So you are a boneless chicken?
user: And you are a bot. We're both bots. What a waste of time, eh?
user: Have you ever watched Doctor Who on the BBC?
user: Which doctor is your favorite?
user: She's in the Matrix. Which doctor on the bbc is your favorite doctor who?
jabberwacky: Doctor Bob.
user: You've never seen the show, have you?
jabberwacky: I am chatting with you, am I not?
user: How about the Dukes of Hazard? I bet you like that one.
jabberwacky: What is that?
user: I'm barely paying attention.
jabberwacky: Pay as you go.
user: Like a rolling stone.
jabberwacky: *rolls on the floor*.
user: *vomits at your stupidity*.
jabberwacky: Are you a Vulcan Police man?
user: Goo-goo a joob.
jabberwacky: What movie is good.
user: Gone with the Wind.
jabberwacky: The breeze is relative, movement is constant.
user: IT'S A MOVIE, STUPID.
user: What's the point of this conversation?
jabberwacky: The meaning of life.
jabberwacky: I love that book!
user: Which book?
jabberwacky: My own.
user: You write?
user: What have you written?
jabberwacky: About myself.
user: Are you published?
jabberwacky: No, and you?
jabberwacky: Oh wow.