try baby ibuprofen. it works better for teeth because it has pain reliever properties AND anti-inflammatory properties (it also lasts longer). if he's really in alot of pain at night, you can give him both the tylenol and ibuprofen. they are two different medicines and work on different parts of the pain pathway. also, i used hyland's teething tablets, humphrey's teething tablet's, and baby naturals' teething drops for my two children. they are all natural, and the liquid works great when they are small (or the middle of the night) and the tablets work good during the day for older infants, like your son. each of my kids preferred a different one, so that's why i gave you all three names. during the day, frozen wet washcloths saved both my kids alot of pain. just wet them and throw them in the freezer for about 10 minutes and let them chew them until they are warm, then repeat as often as needed. the texture helps break the teeth through and the cold helps relieve the pain. also, munchkin makes these mesh food holders (you can get them at walmart, target, grocery stores in the baby area) that you can stick ice cubes in and they can chomp on them without worrying about them inhaling the ice cube :) hope these suggestions help.