Well if he's like me, he will want to know the truth of your feelings sooner or later.
He sounds very insecure with you around other people that our guys (while it's cute, it's a problem in it's own). Try hanging out with him and best friend at the same time. Let them get to know each other.
And yeah it does suck when you go back into not being happy. I don't know. I just have an ability to accept an unusually high amount of bull**** and just not care anymore. Handy but it was hard to build such a tolerance.
Really? I'd rather have a dream where I get to go on some date with some girl. Yeah it lasts for a very short amount of time and most likely a one time deal but it's nice not being alone for once in your life.