‘Okay. Let’s talk about you, then. Your lime-green jacket – are you happy with what it achieves for you?’ ‘Yes, very.’ ‘Okay, moving on to your baggy trousers. Are you happy with how flappy they are? Could be quite a distraction in windy circumstances.’ ‘I wish they had slightly less billow, but I’m happy with the freedom they gift me, especially when I’m having a sit-down.’ ‘Good answer. Now, I know you are happy with your DMs and your hairstyle, so I suppose that’s you covered and concluded appearance-wise.’
I feel like this is exactly how Bob makes conversation, and so although it may feel extremely contrived, it plays realistically in my head.

