You poor thing! My DS had shallow latch, and it drove me to tears too. makes it very difficult to hook them on when it hurts soooo bad. I took mine to the baby chiropractor. Made it much easier for him to latch and also I think simultaneously my supply settled. He was sitting funny while waiting to get out, and the chiropractor said it effected his palette (?! spelling) but that a pacifier can help to level it out. He was very one sided feeding since he was uncomfortable on one side but once he loosened up after seeing the chiro he was away. I pumped through the pain until my nipples were better giving him EBM in the bottle and then once the pain had gone tried latching him again, its also hard for them to latch when you are really full and they are hard, I used sheilds for the first 2-5 min of the feed to soften them up then whipped them off and fed direct. I fed him one side 20min then the other until he was full and hopped off. but he was 9lbs born so needed more I think. not sure about that for you, but I think everyone else is right feed one side till theres nothing left (I used to feel mine before he hooked on so I could feel it after to tell if it was empty). Hope you come right, good luck.