This is an article I found interesting, I liked how it touches upon some of the reasons why it was so confusing for me to figure out how to be "cool" at that age and how it felt like a constantly moving target:
Cool and childhood: How cool evolves from grade school to high school to adulthood.
Does being a "grown ass man who watches Adventure Time" make me cool now?
Cool and childhood: How cool evolves from grade school to high school to adulthood.
Does being a "grown ass man who watches Adventure Time" make me cool now?