Easily the worst thing I've ever made.
From my project summary: Here, the player is first asked to identify him- or herself according to a set of digital "dolls," then given a set of "dollhouses" and instructed to place a variety of other dolls wherever he or she believes they best fit (in the same sort of manner that small children will play with this type of toy). Complicating the situation is that the collection of dolls represents several distinct races, ages, and both genders, while the dollhouses include locales such as a school, an office building, a jail, and a stereotypical domestic house. There is also a stage featuring "dress-up clothes" for the dolls, representing different occupations. The intent of the game is to make the player uncomfortably aware of his or her (and by extension, society's) choices as to where the different types of dolls best "belong."
I want to make it obvious that while it's easy to claim one's sense of "fairness" in an academic or professional setting, in the wider field of casual society, humans naturally make snapshot judgements about others on the basis of preconceived societal notions and structures.
I like to think of this as representative of the larger social "game" that exists, and while this game itself does not provide or judge responses to be right or wrong, one of the potential solutions that arises out of it is that the only way to end this game is to refuse to play.
On a technical note: This game has infinite potential for expansion, so if anybody can think of more awful situations to implement, please don't hesitate to let me know!
"Jaunty Gumption" Kevin MacLeod (incompetech.com)
Licensed under Creative Commons: By Attribution 3.0