Weaning off Bottle to Cup
We have three kids and I don't remember this being a issue. Perhaps this isn't helpful, but maybe it'll be no big deal. We never had a bottle in the crib, so perhaps that helped us out. Early we tried to have them only drink at the table, so that's probably good as well.
When we went from bottles to sippy cuts, they dribbled the first couple times, but when we showed them how to do it, they got it quickly. I really don't remember an issue. Going from sippy cup to regular cup was also messy-- but only for a few days (except for the occasional spill). The older child asks for a sippy cup, like her younger sisters, but given the choice between milk and no milk, she opts for the milk. Quickly.
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