Just had my third baby he is the first I’ve had that will latch. With this he does not have a great latch, and it is painful. I do supplement when needed, would get a larger more “boob” like bottle help his latch?
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Try different positions. I find laying down with baby along side me was best for me
Make sure his mouth is wide open . Like when he is crying etc . Then , you can put him on the breast and make sure he is getting as much in his mouth as will go in . Then he can latch on easily . Took me a few times and it worked . A lactation nurse also helped me