Fortunes may dip and rise; unlike this, good perspective can be depended upon. Long may you continue to be thankful for each thing you do have! That being said, I hope better news isn't too far away for you =)
Sister and I had a pizza party today. It ended up I didn't have to teach him how to make balloon animals. I didn't end up telling him anything, either. We had a good time talking with the people that came, and then they had to leave, and then he, my sister, and I talked. I learned more about him, anyway. Also, I'm pretty terrible at telling if a guy is flirting. I think we might be flirting with each other, though.
In my experience, flirting is most effectively perceived while one is at the peak of the bell curve of intoxication. Drink too little and your insecurities will interfere with your ability to gauge whether he's flirting; drink too much and you are, well, too drunk to tell.
I second Quendalon's advice. A drink is good to relax you, five is bad because you fall over. If he's flirting with you, great! But you may have to be more direct...