Update: I got DD to take the sippy cup about a month ago. She uses the Gerber NUK sippy cup that is designed for transition from BFing to cup or from bottle to cup. It's the only cup I've seen with a soft spout and worked really well for her. It only took a few days to get her used to it. After I saw her drink juice from it I knew she was just being stubborn about the milk. There was a little crying involved, but not too much.