It's not stupid! It just won't work, as you are finding out! So, you have to stop yourself, because not only will it not work, it will work against you. Try to remember that, maybe think about it just before you know you'll be seeing him. Don't ask him about his plans, don't tell him about your dreams!
I'm going to try to read about your sitch in the next day or two, so you don't have to type it all again!