Inspired by discussions of cross-gender roleplaying on [The Forge]: the specifics and the resulting discussion on ToothyWiki have been refactored to RolePlayingGame/Taboo.
Consequently, one of the rules of the game is that your character MUST have a background that is different from yours in at least one major way: different sex (or Gender), A different Sexuality/SexualOrientation: Black as opposed to White as opposed to Asian: Rich as opposed to Poor: and so on.
Character creation relies on free-association based on the player's favorite color, and using this to fill in occupation, interests, and the major obstacles to a long-lasting relationship.
It's a two-player game. Gameplay consists of one player alternating Guide (game-master) duties with the other, attempting to describe a series of romantic misadventures during the two character's first three dates. Having things in common (Compatibilites) and describing mishaps improves your chances of a success on the roll following each scene: enough successes on the die roll can be converted into either Attraction points or named Compatibilites.
Now, the beauty of this is that the Attraction score and Compatabilites do not dictate the outcome of those three dates: they merely suggest a resolution to the players.
IMHO, this experiment is a bold one, and works well enough, though with a few pings in the engine. It's a cute game, and in a discussion of it on the Forge where they were musing on its use as a, well, icebreaker, an acquaintance of mine piped up "It has a non-zero chance of helping two people fall in love. Just speaking from experience here," which was cause for me to [squee] uncontrollably.
The only problem with this game is finding someone with whom you would feel comfortable playing it.
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BreakingTheIce