Myturn I was the same everyone said my attachment looked good but it was still uncomfortable. But I've found in the last week (Ad is 5 wks now) I think his little mouth is bigger and more able to latch on and I think it takes a while for your nipples to toughen up, seriously! I find when Ad latches on first it stings a bit then it eases. But definitely get help with this. I went to our local child health clinic for help. And practice lots, don't be afraid to break the latch as many times as you need in one feed until it feels better. Have you checked for tongue tie also? Just another thing to check for. But I think it's when they're teeny mouth is not able to take much areola and they nipple suck it hurts and it should get easier the older she gets. Good luck