Save the Date is one of the more clever games I've played in recent memory. It's a visual novel with a simple premise: go out to dinner with someone. Well, it should be simple, except every time you try it, the dinners turn into scenarios that would be right at home in the Final Destination movies.
As if the pressure to be good company at dinner weren't enough.
But more interesting than that is that the game knows you're going to reload and try other stuff. It expects you to, even. Dialogue options on retries will reference stuff you did on other playthroughs, and each new playthrough sees you using knowledge you gained in a bad run. Reloading and trying again is stuff we'd normally do when we don't get our way while playing something, sure, but it's still neat to see a game account for that/work it into the gameplay.
The game also uses all that knowledge to make a clever point about the odd, kind of dehumanizing way we play games. Like I said, it's clever stuff.
I'd say more but I don't want to spoil too much -- give Save the Date a try here. You can get through it in about 30 minutes, and it's well worth your time.