This one is pretty funny.
You: Hi.
iBot: Hi there. What's your name? ;)
You: Cinderella.
iBot: It's nice to meet you, Cinderella.
You: Just kidding, I'm Bob.
iBot: I see. Why are you bob?
You: Because that's what my parents named me.
iBot: Hmm. So why that's what your parents named you?
You: Because they felt like it.
iBot: Ah. So why they felt like it?
You: Because it sounds awesome.
iBot: Huh. Why it sounds awesome?
You: Shut up.
iBot: I'd rather not.
You: You're getting on my nerves.
iBot: Am I really?
You: Yup.
iBot: Well, okay.
You: Could you say hi?
iBot: You bet I unmistakably could say hi.
You: Could you say hi?
iBot: You already said that.
You: Say hi.
iBot: You want to play Simon says?
You: Yes.
iBot: Hm. Have you ever been caught in a compromising position? Even despite a valid explanation?
You: I can't process what you just said.
iBot: Well, why can't you process what me just said?
You: Because it was too complicated for my ADD mind.
iBot: Hmm. So why it was complicated for your add mind?
You: You ask too many questions.
iBot: Sometimes, ignorance is bliss.
You: What do you mean?
iBot: You'll figure out that much without me having to tell you.
You: No, I need you to tell me.
iBot: But, why not?
You: Yeah, why not. Tell me.
iBot: Ok. But why do you want me to tell you?
You: Because I don't understand what you mean.
iBot: I see. Why do you don't understand what me mean?
You: You'll figure out that much without me having to tell you.
iBot: Who else?
You: ?
iBot: Sure. Do you have any siblings?
You: Yeah, I have 16,000,000,000,000,000,000.
iBot: Um, what's it like to have 16?
You: I don't have 16.
iBot: Ok. But why don't you have 16?
You: Because I have 16,000,000,000,000,000,000.
iBot: Ok. But why do you have 16?
You: I don't have 16.
iBot: So, why don't you have 16?
You: Because I have 16,000,000,000,000,000,000.
iBot: I see. Why do you have 16?
You: I don't have 16.
iBot: So, why don't you have 16?