Tim's routine here is the classic "joke that won't die."

But I think it works better when you keep coming up with new variations of the joke, as here, than when you just draw one joke out and out and out, as on, say, Family Guy.

Will's little exercise here is an attempt to get Rikk out of his shell—yes, Rikk still has a "shell" when it comes to talking to girls in any sort of romantic setting. Poor Rumy doesn't realize that Rikk is usually self-assured around her because he doesn't think of her as a romantic possibility.