Paper Dino Software's Save the Date is a rather unique game. You play as an unnamed character who is tasked with arranging a date with the object of your affections, Felicia. It plays out as series of multiple-choice questions, but after spending some time with the game, you'll discover that the stakes are far higher than the average dating sim.
Save the Date is a powerful, frustrating game, and one that's well-written and ingeniously designed. For maximum effect, you should discover the game's overarching concept for yourself, so we won't go in-depth into its finer details. Once you're done with it, there are a couple of great reviews of the experience on Rock, Paper Shotgun and Geeky Universe. It's available as a free download for Windows, Mac, and Linux.