William's right eye used to be very watery when he was a puppy and by the time he was about a year old it looked really soggy sometimes. I took him to the vet and was told the tear duct was blocked, so he had a procedure to unblock it. That stopped the problem for about a year but it then came back and a second procedure was only partly successful. At that point I was told that the tear duct was narrow and would probably never work efficiently.
A few years later William was diagnosed with Dry Eye in both eyes, but the right one the worst affected. I've no idea if the narrowing of the right tear duct noticed by the vet when Will was 2 was the first symptom of Dry Eye, or not.
I'm not suggesting that Riley has Dry Eye, but it may be worth getting your vet to check his eyes in case he has blocked tear ducts. It's a simple test. They use a green dye, which makes the eye look very strange for a while, but if the tear ducts are functioning normally some green dye will appear from Riley's nostrils within a few minutes.