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See if he likes apple juice or something sweet. Then put it in the sippy cup, get him use to thinking that is where the juice is. Then switch it and give him milk. I understand your concerns I just sucessfully weened my 18 month old. I was one of the hardest things that I have ever done. The beginning is hard but its rewarding when you see that you child can stand on his own.
It may take some crying and some fit pitching but it will end.

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