Peaking in High School is rough. He might not even be conscious about what he is doing. Call him out on it next time he does it. See where it goes.  If not addressesd just going make you want to spend less time with him. Eventually killing the friendship. Sadly in the fiat standard mid 30s I feel like more people are trending the way of your friend. 

 I would say that he’s totally and completely normal for the millennial generation which is depressing. 

 Yea I see the same with the people I went to high school with. Very depressing. Fiat standard way of life taking souls.  A lot of unhappiness out there.   

 One of the hardest things is to watch somebody you knew when they were young become old and bitter. Because you remember them being light and happy.