Is he having any colored discharge? When Scout has problems with a clogged tear duct her eye will sometimes even get a milky looking film over it and it waters when she eats or drinks. The vet told me not to worry about it since it always clears up in a few days.

Better keep a close eye on Allen to make sure it isn't a scratch or some other irritant. If you start seeing any green discharge then you need to get him to the vet for sure. Please keep us posted.