I have played a bit more Save The Date since the end of this video and it gets a bit more philosophical though I am yet to find a way to "win" that doesn't involve being an awesome hacker.
It is pretty clear that the Chris was trying to say something when he made this game, it feels like a very safe assumption given that Felicia will outright tell you that the creator must have had an idea they want to explore.
To me Save The Date is an exploration of an exercise I think everyone has done at some point. Running back through a day or series of events wondering what you could have done to prevent that big mistake/regret/loss.
In real life this is about as futile as it is in Save the Date, you can't change the past just as you cannot really save Felicia if you go out with her. Instead the game forces disaster at every single turn. In the end the only way to save the date is for it to never take place at all.