He recently has all his teeth taken out fot stomatitis, as well as some moth eaten teeth they found before taking the others out.
He is not this sweet normally. He was too stoic to catch the pain he was in previously.
Bonus post surgery not happy picture. 
No bad intent here, just curious, how do cats eat after having their teeth removed?
Perfectly fine.
My cat had the same tooth removal surgery a couple years ago (he was adopted with a mouth full of teeth where most were about to fall out). He was on soft food for about 2-3 weeks before he started picking at his dry food again. Now he gets a portion of wet food every morning, and free feeds dry all day.
What I learned from the vet is that cats use their teeth mainly to rip meat off their prey so they can swallow it, and not really to chew. So if they're presented with food that's an appropriate size to swallow, they just swallow it.
Well that's certainly not the whole truth the way mine can be heard crushing on his dry food from multiple rooms way
My understanding is that if the food is easily swallow sized, they may unintentionally crunch as they maneuver the food around their mouths to position it to be swallowed, but not out of necessity. If the food is larger, sure they'll break it up so they can swallow it easier. But by nature, cats aren't animals that need to chew food for grinding and digestive purposes (like animals that have flat/grinding molars.) As long as they can swallow it, they don't need to chew.