This is a picture of a loving couple cuddling and playing Diablo 3 simultaneously. I like how the girl gets the desktop and dude gets a crappy laptop on an ironing board. That's a great metaphor for relationships.
Plaid Wool Jacket, Polka Dot Scarf (This is most probably too preppy for John, but I could see elements of it working for him. The vest and scarf and instead of the blazer take that pattern and put it on the pants.