I have an EBF baby that is 5 monthes old. He gets a bottle 2 day a week due to me working part time. He is still using a new born size nipple. Should I up the nipple flow or switch to a trainer sippy cup?
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Nope, you never actually need to change the bottle nipple. Your breast nipple never changes its output so why should the bottle? (That’s not a serious question that is a quote from a lactation consultant I worked with.)

Is he refusing the bottles now? No need to go up a nipple size unless baby is indicating they want a faster flow. I don’t know what a trainer sippy cup is though, we just use straw or open cups with our kids.
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