There is a question that I'm told is popular to ask incoming freshmen: "Which historical figure (Jesus, Gandhi, Ozzy, etc.) would you most like to have lunch with and why?" Now I have no idea what quality in the student this question is supposed to elicit, except perhaps forbearance. I'm glad that no one ever tried it out on me, because most of the answers that occur to me--"Is that likely to happen if I decide to attend this school, sir?"--probably wouldn't help my case. When the list of candidates is specified in advance, they're typically chosen either because they are (in)famous icons of recent pop culture or because they are timeless sages who have already provided written answers to the most common set of meaning-of-life-style questions. As much as I might rather meet Lao Tzu than Elvis, my hunch is that it would be more in keeping with Taoist principles to dine with someone who speaks your language and shares your preference for Southern fried cooking. I could be wrong about that.
The whole dining with the stars thing puts me in mind of the Turing test. Alan Turing famously argued that we'd know that a computer was intelligent when its conversational interaction was indistinguishable from a person. Because people and computers look differently (android fantasies notwithstanding) he suggested a situation that would cloak the embodiment of the interlocutor. The person who is conducting the test takes turns asking questions of two different respondents via a low-bandwidth connection (think IM). If he or she can tell which one is the computer, it fails the Turing test.
In 1966, Joseph Weizenbaum created a conversational program called Eliza. Eliza could read an incoming statement like "I hate dogs" and use simple transformational grammar to turn it into a question "Why do you hate dogs?" It could offer noncommittal responses like "Please go on." If the person answered a question with "Yes," Eliza might say "You seem positive." Many people interacted with Eliza enthusiastically, leading some to say the Turing Test had already been passed and others to say that it was rubbish. (If you'd like to converse with Eliza you can Google for one of her many incarnations.)
If I were chatting with freshmen, say over lunch, I'd be looking for students who had heard of Eliza and the Turing test and had a well-developed sense of anachronism. That hasn't happened to me yet. As a public service, I'm going to offer a new question that has been updated for the digital humanities: "What challenges would you encounter when trying to create an Eliza-style simulation of each of the following historical figures? Which would be most or least likely to pass a Turing test and why?"