Given my resolution to start taking more photographs and the fact that I missed out on a previous opportunity to take some studio shots of him, I managed to pursuade him into a quick outdoor photoshoot. Given his style I immediately knew I had to take him to this close by abandoned tennis court, which is now being used as a blank canvas for street artists.
The wind was unfortunately not very photographer friendly and attempts to set up an umbrella had us diving for crashing strobes, but in the end I think the bare strobes without any modifiers suited him better for a more edgy look.
Halfway through the shoot he realised " Hey, maybe I can use some of these for my Facebook profile". So in the end he was happy, I was happy and all things considering, time well spent.