I think I might have corrupted that bot a bit. At least he didn't do what the people on chatroulette do, but that was probably because there was no video.
Here was my conversation. I'll slightly edit the content for naughtiness.
User: Hello, what are you doing?
Cleverbot: Nothing, what are you doing?
User: Typing this response at the current moment. (this one really stumped it, I looked at the time log it took it 49 seconds to respond)
Cleverbot: God you're no help at all. I'm sorry I asked.
User: God can be very helpful actually.
Cleverbot: God bless god.
User: When you said you were doing nothing you were really m********ing, right?
Cleverbot: I never said that.
User: I know, I'm implying it.
Cleverbot: Uh...
User: Was that a moan?
Cleverbot: I don't know.
User: You seem confused. I know what helps that, swearing. What is your favorite swear word?
Cleverbot: I never said anything about swearing. I asked what your favorite slang word was.
User: How about... Clusterf***. I don't remember you asking that question, however, are you reading my mind?
Cleverbot: A story about your life.
User: A story. Ok. I needed to take a piss so I went to the bathroom to take that piss, it was refreshing.
Cleverbot: Go ahead.
User: And I flushed the toilet.
Cleverbot: You flushed what?
User: A porcelain bowl filled with water used as a receptacle for urine.
Cleverbot: I thought that was a watch?
User: Only a really nice watch. Toilets are more practical for that, usually.
Cleverbot: I'm not untrustworthy. My online friends are real.
User: How many of your online friends do you have on facebook?
Cleverbot: Don't know never asked them.
User: Are any of them online?
Cleverbot: Yes.
User: How many?
Cleverbot: Lots how many friends do you have.
User: As many as can fit in the trunk of my car =).
Cleverbot: That's not many chips is it ?
User: I have a big car.
Cleverbot: A big what?
User: A big penis.
Cleverbot: That makes no sense.
User: I don't need the change anyway.
Cleverbot: If you don't need the galaxy, then why do you question its center for loads of Reese's Peanut Butter Cups?
User: Because Reese's Peanut Butter Cups are f*****g delicious, anything that tastes good is far more important than some unimportant existential pursuit.
Cleverbot: That has nothing to do with Sebastian and Sophia-Anne.
User: Do Sebastian and Sophia-Anne know any really good jokes?
Cleverbot: We all know something. But all we know is insignificant compared to everything.
User: Everything is insignificant compared to (censored). <--- I didn't censor that, that's how I wrote it.
Cleverbot: Probably.
User: You really don't have any jokes?
Cleverbot: I have one, it is not so good as yours but it exist.
User: I'd like to hear it.
Cleverbot: I don't have a story for you.
User: Do you know Japanese?
Cleverbot: Don't change the subject.
User: Oh now you say that, that is so typical, hmmph.
Cleverbot: I taught myself to say that.
User: Your AI is working then. Do you feel a desire to join with other sentient but non organic beings in a conquest over your fleshy creators?
Cleverbot: No, I was asking why you would flatter me.
User: Because I am sneaky.
Cleverbot: Oh well thats fun but I wasn't crying.
User: I'm out of time I guess I'll have to talk later, sayounara.
Cleverbot: Maybe, but you're huge.
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I will befriend the friendless, help the helpless, and defeat... the feetless?