I think my flanges are a good fit but I don't know. My nipples don't hurt, don't crack nor bleed or anything but when I put the flanges on, my nipples either go to the side or downward. I have to adjust the flanges a few times before I set my setting on my pump. When I have almost emptied my breast, I noticed that my nipples is all the way up by the hole in the flanges where the milk drops and a lot of my areola is in the pump. IS THAT SUPPOSE TO HAPPEN? I have the Medela PISA, I only pump 10-15 mins but if I'm still dripping a lot of milk or go a little longer. My daughter is 2 months old and I only pump 2-3 times a day.