I'm glad you enjoyed it! My reasoning behind the seemingly arbitrary point changes was that the score boiled down to Saul's own opinion of himself, rather than to any actual success with Alan (in fact, to pull the curtain back a little, whether Alan enjoys the date or not is actually an entirely different score value - the only thing Saul's perceived score affects is some small dialogue here and there, one split in the middle of the game, and whether the Game Over screen is triggered or not). For the food choice, I'd even say that the one that lowers the score is (arguably) the better decision.
I definitely understand how it can be confusing, though - at the end of the day managing to convey all that via the game is quite tricky, and with the power of hindsight I can definitely see places where I could have made it clearer. I suppose that's how it is with game jams, though.