Your great idea reminds me of Timothy Leary's Mind Mirror!

Electronic Arts published a role-playing personality analyzing game called "Mind Mirror" designed by Dr. Timothy Leary. It actually let you make a "mind map" of the personalities of historical figures, fictional characters and friends, plot them graphically, compare them, and take them through role-playing situations to compare the consequences of your decisions with their idealized personalities.

http://en.wikipedia.org/wiki/Timothy_Leary

* Equal parts party game, roleplaying game and social simulation, Timothy Leary's Mind Mirror was released for Commodore 64, Atari XL, Apple II, and MS-DOS computers by Electronic Arts in 1985. The game was a digital reinterpreting of Leary's doctoral thesis.

He later stated that he had plans to release an updated version of the program with advanced graphics (including Apple Macintosh and Amiga versions), but that never occurred.

http://www.picofactory.com/abandonware/mindmirror

Mind Mirror allows the performer to digitize (scope) any thought, compare it with other thoughts and compare thoughts with others, and to engage in simulation of various roles.

Can be considered a "party game" like Scruples.

http://sjc.blog.uvm.edu/archives/2004/10/timothy_learys.html

Timothy Leary's Mind Mirror

"The purpose of a mirror is to reflect."

Timothy Leary's Mind Mirror is a "game" published in 1985 by Electronic Arts. It's a "game" only in the sense that no one can otherwise make heads or tails of it - there is no winning, no losing, no scoring. It is, however, deeply interactive, multi-media (of sorts), and hypertextual. Each play of the game results in a mind map - of you, your family, oyour friends, of a leader in history, your pet cat.

The vendor observed "Mind Mirror allows the performer to digitize (scope) any thought, compare it with other thoughts and compare thoughts with others, and to engage in simulation of various roles." MobyGames classified it as a Zen / Meditative sport.

Popularly considered "abandonedware", a 16 page "user manual" (pdf) and an executable MS-DOS version (zip) can be downloaded from The Underdogs.

http://www.geocities.com/SiliconValley/Code/5104/gazette/march1987/Alter.htm

To a greater extent than Alter Ego, Mind Mirror delves into human personality. This program goes about its exploration, however, in a different manner. Dr. Leary’s program employs pie charts called "mind maps," which gauge your chosen personality according to 16 attributes. The attributes include charisma, arrogance, dominance, submissiveness, and anger. The mind maps look like dartboards, and display your personality’s rating for each attribute. The closer the attribute rating is to the outer edge of the pie chart, the stronger that attribute is manifested in the personality. The attributes are arranged on the chart to correlate with each other, so that the location of the rating for one attribute shows tendencies of other attributes.

In similar fashion to Alter Ego, Mind Mirror gives a lot of flexibility in choosing a personality to use in the program. You can use your own personality, your favorite celebrity’s, or a custom proffle created by you. However, instead of asking true/false questions like Alter Ego, Mind Mirror requires you to rate the subject personality on its attributes.

This is accomplished using questions concerning the attributes and answering the questions by rating the personality on a scale ranging from never to always. An example phrase of such a question would be "nervous at big parties." You would rate your subject according to whether he or she would always, often, sometimes, seldom, or never be nervous at a big party. Once you’ve run through the ratings, the mind maps are available for review to see how the personality’s attributes appear.

From that point, Mind Mirror takes you through exercises that seem to test your ability to figure out how your chosen personality will respond or react to the exercises or situations presented. You can examine a personality’s opinion on various subjects from religion to politics, or you go through life simulations similar in concept to Alter Ego. Again, you use a rating system in response to the program prompts, which are later compared to the personality’s attribute ratings on the mind maps. The objective is to try to respond to the exercises or simulations as your personality would, and, accordingly, have your responses produce a mind map identical to the mind map of the personality profile.

However, the genius of the program is the insight the user gains from setting up the personality profile and going through the exercises—the user is testing his or her own perceptions. First, a subject’s profile is chosen for examination. But that subject’s personality traits are determined by the user. Therefore, the subject’s attributes are not necessarily true attributes, but rather the user’s perception of the personality attributes. Furthermore, the exercise is really a self-test or quiz on the user’s own perceptions, which results in both subtle and astonishing revelations for the user about his or her own personality.

The program adds depth to its enjoyment by offering several levels of play, progressively reducing the amount of prompts and "coaching" you receive. Also, Mind Mirror can be played by groups or teams, making it an interesting party game. Dr. Leary even has made provisions in the program for its use by professionals in their treatment of individuals and groups.

Mind Mirror comes on two disks, with the 2000 available life simulations on both sides of one of the disks. The manual is informative, interesting, and brief. It does not, however, need to be very involved because of the nature of the program and the amount of on-screen prompting and aids. The manual does give you some interesting background into the evolution of human thought, or at least Dr. Leary’s theory of human thought. Also, the manual contains an interview with Dr. Leary on the program, psychology, and life in general.