Out with Jack

Went out with Jack for a drink.  I think maybe we were just nostalgic, because we talked about some of old friends and the memories we had. 
Jack is one of those people who views high school as an okay experience.  Since Jack and I went to high school together, this is a view that kind of boggles my brain.  He was such a nice guy, but occasionally people were awful to him, and he witnessed the same injustices and problems that I did.  I guess I am less easily impressed. 
As much as like Jack, sometimes he does this thing which indicates he's either not listening or he doesn't want to listen.  He always does this when I state how happy I am, which these days is anywhere from moderate to almost perfect.  I'm not sure what this is about, exactly.  Maybe he thinks I am lying about my happiness?
...I have to admit that I haven't been as happy recently as I once was, but happiness is a lot about attitude and not necessarily what you do or do not have.  If you make it a point to try to be happy, it makes a big difference to how you address the unhappy circumstances in your life. 
And this attitude is a change for me, at least in comparison with my high school self.
This is the one thing that I think is preventing me from being closer to Jack.  I want to get closer to him, but I suspect he doubts my honesty.  It hurts a little, to recognize that.  And it hurts to realize that he's probably keeping me at arm's length.