Interesting situations but I think sometimes our precious little darlings do love the attention and try to manipulate us into satisfying their every whim.
What has been said before, by Karlin and others who have been through this situation is, go with the tough love. You are the one in charge and you should decide when, where and how the food is presented. Most Cavaliers prefer a very shallow bowl rather than a cavernous deep one, so strart with an easy clean small, shallow stainless or ceramic.
Put the food down, tell the dog it is time to eat and give him 15 minutes to decide whether he will eat it as presented, or not. If he chooses to whine and look up at you with those melting manipulative eyes, be strong, ignore it and go about your business. If the food is uneaten after the time limit, then lift it and, that's it folks, no food, no treats (only water) until the next regular meal. Trust me, these dogs are going to eat eventually if they are healthy to begin with, they won't starve themselves, although they want you to believe that they will. (Little stinkers that they are.)
When I was a police/fire dispatcher we would get the occasional call regarding a cat "stuck" up in a tree. The callers thought the fire department should always come out with the ladder truck and get them down. Of course, we would tell the people that the cat will come down when it is ready. One woman who refused to listen and was insisting that we dispatch a truck was finally put on the phone with the watch commander of the day. He asked her, "When was the last time you saw a cat skeleton up in a tree."
Needless to say, she called about 20 minutes later to say that the cat came down of his own accord and all was well. He didn't need to be "rescued." He might have enjoyed the ride down but had to do it for himself, as your dog will also do when you give him no other option!