We've tried 3 times now and only result is that our son starts crying when he see's it. We waited a couple weeks in between each attempt. Again, we tried Saturday morning, and he has refused to drink anything, so being Sunday afternoon, we finally gave in. We have done our research! We need more help other than, "when he's hungry enough he'll drink".
It sounds like old habits (drinking from a bottle) are hard to break, and that thus far, you’ve done your best to help your child transition to a sippy cup. One way to help ease the transition is to have your son go with you to a store to pick out a new BPA-free plastic cup to drink from, whether it’s a traditional sippy cup, a sippy cup with a straw, or a regular plastic cup. You can also allow him to pick out a child-sized BPA-free water bottle that he can have when on-the-go. While you may feel pressure to have your son learn to drink from a sippy cup as many other children his age do, there’s nothing wrong with teaching him to drink from a regular cup (just like many of us did well before sippy cups even existed). And while the transition may continue to be frustrating, it’s wise to not let your child see you sweat and to stay even-keeled and pay little attention when he refuses to drink from a sippy or regular cup. And because you don’t want your son to become dehydrated, make sure he chooses lots of fruits and vegetables and cooked grains to meet at least some of his daily fluid needs.
If you empower your child by allowing him to participate in choosing the cup(s), continue to offer fluid at meals and snack times (especially when he’s hungry), and allow him to have some choice about what to put in the cup (the choices can include plain water or seltzer, fat free milk, or small amounts--up to 4 to 6 ounces per day--of 100 percent fruit juice or some juice mixed with water or seltzer), this will hopefully encourage him to develop healthful age-appropriate drinking habits and meet his daily fluid needs.