I fed DD1 to sleep until she was 15 months. I was 5 months pregnant by this stage and wanted/needed a change. For one week, i asked DH to come home early and settle her to bed and i would offer a feed 20 mins or so before sleeptime instead of just before. After a week she had accepted the change. The first 2 days were the hardest for her & DH but we never left her - he sang and hugged her instead of me feeding. She also started sleeping all night at this point too. She self settled not too much later.
I fed DD2 to sleep until she was 16 months - same method of change with DH settling for a week. But she was waking up to 5 times a night at this time and i would feed her to sleep if she woke in the night. This changed 2 weeks before i gave birth to DD3 as i couldn't envisage feeding a toddler & a newborn in the night. Same method - asked DH to attend to DD3 when she woke in the night and just give water saying mummy milk is in bed, it's sleeptime. It took her 3 nights for the protesting to be just winges rather than crying and a week to accept she wasn't having a bf in the night. Now at 2yrs, she wakes just once, has a big drink of water & cuddle & back to sleep. She self settles very easily at night but i do lie down with her at lunchtime for 5 mins until she's asleep (with newborn with us too!) as she finds it hard to switch off in the day.
So with both, although there was crying we never left them on their own crying - always in our arms. Being consistent really helped keep the message clear for them i believe. And now & again i've fed to sleep when i really needed to - if a child was sick and needed the comfort or whatever.
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