Well, they are both too old, you know this. Your orthodontic bills are increasing by the day. My son was terribly attached to his as well. We first started by only allowing it at bedtime and naptime. This was a two week thing, then we went to the dentist. Now our dentist is a bigger guy, and has somewhat of a loud carrying voice, but is really a nice fatherly type. We were there for my son's three year old visit, the first time there. The dentist had a nice little talk with my son and told him that it was time to get rid of it. Period. My son, being a negotiator, asked if he could just keep it one more. This meant in my son's mind to keep just one of them and not the rest since we had several in the house. The dentist agreed and said "sure you can have it one more night, but tomorrow they all have to go". So we went home and talked about how these pacifiers would ruin their teeth and the dentist said they had to go. So the next day we had a ritual of sorts and said goodbye to them. He tossed them all in the garbage, helped carry it out to the garage, and it just so happened to be garbage day and we brought it to the curb. That night he asked for the pacifier again, but I gently reminded him that it was gone. He did it again the next night, but then never again. I was amazed. When we saw them in the stores, he asked if we could buy another one but I told him that only people with babies are allowed to buy those, and that was enough. Now, I never believed this little ritual of sorts would work, so I secretly hid a couple of them thinking at 3am when I couldn't take it anymore I would give him one, but I threw those out a couple weeks later too. They don't need them. I replaced them with a nice CD too that I still play for him at bedtime as he falls asleep. The one I use is from Discovery Toys, called Sounds Like Fun. It's somewhat of a lullaby of learning. This music was the "big kid" way to go to sleep since he didn't need the pacifier anymore. Hope this helps. Good Luck.