What is Cool?

Last night, with great old friends, I:
-had slice pizza
-went to Toronto's major art gallery (AGO)
-hiked across city
-drank beer on dingy, trendy patio
-hiked across city some more
-went to indie rock show (make sure to mention band is from Brooklyn, New York)

Here is what I loved:
-the pizza (tangy hot sauce a plenty, and a Barq's rootbeer, of course)
-the AGO: lord knows why I'm uber comfortable in that art gallery, love talking to people, to strangers.
-the hiking
-the German wheat beer
-the company, the company, the company (of friends you can 100% be yourself with)
-the originality of the music

What I did not love has more to do with the environment, "the scene," at the dingy, trendy patio bar and at the indie rock show, which leads me to a question:

Why do coolness (of the indie rock/dingy bar variety) and kindness (of the be nice to others variety) hardly ever collide?