I was reading today's cracked article and found potential in a game posted here.

The goal of the game is to choose a random person. That person is now your future self and the goal of the game is to create the story of how you got to look like that by judging by the person's looks, dressing style, etc

The author plays by himself, but I can see it working very well with 2, where YOU choose which person is your date's future self.

I can also see good in playing this alone: it develops your observation skills, attention to details and creativity.