I think Snakecharmer has really fabulous advice ( she always does) and first hand so it was tried and true.

Maybe try to put on "blinders" Take him the yummy food he likes, Talk about what he might like the next visit. If he has friends there maybe you could offer to bring in a cake and you would love to have a lil get together ( check if the friends can safely eat some cake, diabetes tends tends to be common as you well know ) That would focus the visit on a cake with his friends and and you, would take the pressure of you to sit just with him and all that awkward time.

Again Stellar advice Snakecharmer