His problem isn't the philosophizing. That's endearing. It suggests he's striving to understand his good fortune/existential angst. His problem is that he's not any fun. Even when he's having a good time he seems like a lost soul. That's probably what the Army was about. Maybe the whoring too if there's any truth to what his haters above say.
Actually, on that subject, Dylan was recently hanging out (sleeping with?) itsevanwade. Then fly to NYC together, then they split up and Evan gets depressed and nearly quits social media. My question: did Dylan bring him to NY to meet his rich friends and usher him into the easy sugar baby/rent boy life, only Evan couldn't handle it?