Actually, cleverbot doesn't switch you between conversation partners to better fit the situation, here's what happens. Every time someone enters text, it is save to Cleverbot's database. Cleverbot is designed to recognize certain phrases and associate them with certain responses. So, when you type "How are you?" Cleverbot searches it's database for something along the lines of "Good" or "Bad". If you type a jumbled mess with poorly worded things, Cleverbot associates whatever response seems adequate.
So. At form place time thingie; we were talking about who does what at Sports Day when a fat nerd says, "I'll do the long jump." And everyone stares at this fat guy that can hardly walk or stand, wanting to do long jump. So to break the ice, I joke; "Really? Are you going to rocket jump it?" The response from everyone is laughter to which he replies; "Yes." And the serious look on his face was so stern, I'm worried about his mental health… As well as his physical… D:
Just because you don't understand a joke, doesn't mean it doesn't belong there. Ken Jennings made a reference to "welcoming his new robot overlords" when he was defeated by a computer program in "Jeopardy". Willey has made a clever joke, and you try to mock him. You failed, Cheese.