I like this thread. An idea I have with how NOT to introduce people to games:
The only true sandbox MMO- Ultima Online. The player would probably be most likely to ask 'what do I do' or 'how do I win', where there is no 'win'. 'Win' doesn't exist. You can do whatever you want. I love that MMO and its the only one I play anymore, I've tried 31 others but they didn't hold my interest; but that's me as a lifelong gamer. I find things in games that I want to do that the game doesn't let me do, and eventually get drawn towards sandboxes where I can do as I like.
But having someone new to gaming have unlimited choices, it would just make them not interested in the game to begin with because there would be no direction, and they would not have anything in their experience to come up with one on their own, at least not in a game setting. I'd say that having someone play on an N64 would be a bad idea too, because of how the controller is set up, there's no obvious correct way to hold it to someone who hasn't already become familiar with various controllers. Another bad idea might be to know a person's personal fears and traumas, and then have them play a game that exploits it all! Another bad idea also plays on the person's psyche, such as having a PETA member play a game that starts you off killing a random animal for seemingly no reason, or seeing an NPC do it. I'm very sure that stuff would not only turn a curious person away from that game, but the entire game industry, without being willing to hear what anyone has to say about it. The same could be said for having someone new to games that has a weak stomach play the Parasite Eve or Resident Evil series.
Addendum: Everything I say is opinion based.