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All babies are different. I co sleep with my 14 month old son and he doesn't stay latched on all night but he will usually stay latched on for about 5-10 mins every feed and he wakes usually 3-5 times. Have you ever thought to try a pacifier? My son quit his on his own at 10 months so he won't take one anymore but prior to that it was literally my only way to ey loose. I would slowly slip my pinky in his lip when he was drowsy, then replace my nipple with the pacifier and voila!!!!

We don't co sleep thru the night, but if she wakes up earlier than I want (1x a night), I'll often nurse side-lying and let her finish out the night in bed with us. She usually will stay latched on longer than feeding, but will eventually detach and roll off within 5-10 min. On times when she won't detach without crying out, I will try switching a paci for my nipple. Usually, she take the paci and reject that after a few seconds.