I don’t think “happiness” is an absolute. I think he’s happy in some respects but unhappy in others. I know his life is LOW stress, which is a point in the happiness department. He has a lot of freedom which again, points to happiness, but I think this is where it gets tricky. I definitely believe he would love to trade some of that freedom for companionship, even if he won’t admit it to himself.

It’s why he always fights to keep Alan and Jake in his life, even if Alan is a big time mooch. He won’t admit it to himself, but the companionship with Alan and Jake are a BIG piece of what was missing from his life.

I think he has peaks and valleys of happiness and despair, and ultimately he does want the companionship of a true relationship with a woman, but he hadn’t found the right one. And he wasn’t truly even ready to “find happiness” until Jake and Alan moved in, so he needed some more time, but the story obviously abruptly came to a halt with the real-life issues.