Is the glass half full? Or half empty?

Personally if a glass is filled halfway and placed in front of me, I would label it as being half full. But others may think otherwise.
My fiance and I have the tendency to come to totally different conclusions from a single situation. We may look and hear the same things, but it just doesn't mean the same thing somehow. We frustrate each other constantly by not being able to understand each other's conclusion ( ok, let's just say I believe I frustrate him a lot more than he does me), but either way it's not a happy experience for either party.
It's a real worry. Not just in the sense that I don't understand him, but worrying in the sense that I'm placing so much effort in trying to understand him, but still come up interpreting his feelings incorrectly. He even has to give me very significant clues to what he's thinking ( at least I can tell they're significant), BUT, I still get it wrong. It's like being a contestant at a quiz show and getting, "BZZZZZZZ. Sorry that's incorrect" all the time. It's just plain annoying. It would be a lot easier if I could just steal all the gamecards with all the answers, but then I guess that beats having a quiz show. And I guess that beats the "fun" out of a meaningful relationship. You do realise that I would still steal all the answers if I could. It beats being a dumbass any day.