From the way you describe him, it sounds like he is very depressed, unable to care about anything and unable to think about anything negative for fear it will drag him further down... if that is possible.
Of course, thinking that on just a few words is pretty much folly.... but it could be.
I guess segments is a good analogy. Once when I witnessed a Winne The Pooh tattoo on the upper arm of a young woman at work, my mind couldn't help but wonder if she would ever wish she hadn't done that. It was not the idea of having a tattoo itself, but the subject of it. I knew when I was 30, I didn't love or see value in a lot of things that I thought was good or valuable when I was 20 and when I was 40, once again, many things had changed in my likes and what I was into when I was 30... and on and on. Times change and life changes nearly completely as time goes on.
You just never know for sure what drives someone else to care or not.
I'm not sure what that chaps problem is, I try to avoid seeing him much because he whined and complains and things, feels he is the victim, but chooses to take no responsibility for himself, thoughts, attitudes and actions. It's always someone else's fault when, in reality, it's not; it's his. On the occasions I see him I keep it as brief as I can which works for me; I can get back to my vibrant and colourful life, and he can get back to his dull and lifeless one. Everyone is happy.
Lol, tattoos are a good example of how life progresses; I've seen some very bad choices made in that regard. I have tattoos but am lucky to have put some forethought into it.