This game has been on my wishlist longer than almost anything else, and I no longer remember why I put it on there, but it was fun.
It's a mini-IF, made for a speed competition, one of the earliest I know of (held in 1998, the same year as the first of the long-running Speed-IF competiitions).
Despite being short, what's here is surprisingly detailed. You're a young girl with a crush on Randy and the two of you happen to be playing a board game together. While you hold the key to victory at any time, the other girls suggest you let Randy win so that he'll be more open to your romantic overtures. "Boys like to win," they say.
There are at least two endings to the game, which was a condition of the original competition. I thought it was a pretty grimly humorous depiction of a lot of guys I know. I knew this one guy in college who dated my sister and he would get so genuinely upset when he lost at card or board games that we would all let him win just to avoid his temper tantrums.
Overall this was pretty great. It's small, but not rushed. It can be won very quickly, but has a lot of great detail.