I like how anti-"fun" he is :

Is he though? If he was "anti-fun" I don't think he'd have made this statement.

I used to be part of the Territorial Army (now known as the ‘Army Reserve’) and spent most of my weekends in cold, muddy puddles getting shouted at. When I looked back on the weekends, I’d somehow convinced myself that I’d had a great time playing soldiers. So I put this to the test and one weekend I decided to write down how I felt as it happened. I realised I hated it. That was my last weekend with the Army.

Dude is all over the map, actually. It's not his fault, happiness is a complex concept (it's no wonder people struggle to achieve it). He seems to jump back and forth between the concept of happiness as approached by pursuing pleasure and contentment as approached by detachment, discipline, and self understanding. Not surprisingly, he finds arguments that validates and invalidates both. The whole conversation is unfocused, which is understandable, because it looks more like it was an interview instead of a thought out, planned, and focused essay. Even if it was, I don't think the concept of happiness, pleasure, fulfillment, contentment, suffering, and struggles could be tackled in so few words.