I had (have?) one flat nipple and one "regular" nipple. When DD was born, I couldn't get her to latch on the left side. Nothing made the nip "perk" up. I got a breast shell (looks like a donut with a cap over it) to help draw out the nipple. I remember I wore it all the time, and when DD would nurse on the other side, milk would flow and fill the cup up! I didn't realize it though and milk would spill all over the place and I would get so flustered.
Anyway, it took quite a few days and many attempts to get her to latch on that breast, and eventually she did. I did pump that side when she couldn't latch and I got too engorged. Sometimes just pumping for a few min to get the milk to flow was enough to get her latched on.
I guess it's not flat any more, b/c both nips perk up the same way now when she nurses and when it's cold. I don't expect to have problems with future nursing children, but at least if I do I know what to do.
Good luck!! <3
SAHM to Nora Caitlyn ('08)
and Finnley Dax ('11)
homebirthing, breastfeeding, babywearing, intactivist, doula mama!