Evenings can be so tiring when they won't settle
Dd used to self settle, but it didn't make her sleep through the night. The only thing that improved night times was night weaning her at 18 months (I was pg)...but then I had to give her bananas in bed because she was so hungry! Some babies need constant food and dd was always a very frequent feeder (and still is, although now it's hard finding a million nutritious snacks a day).
Dd will settle without a boob now, but we still lie down with her. It's easier when they're bigger and you can reason with them a bit more.
I think it sounds like feeding to sleep works great for you...but you might need to tweak the evening ritual so dh doesn't rev up your ds too much...otherwise I would look at the number and timing of day sleeps so that ds is really ready for bed at night, so he only needs a quick feed.
Hth
I fed DD2 to sleep, DH rocked DD2 to sleep and we both walked her in the pram around our big hallways in a circle to get her to sleep, and it worked fine, if it ain't broke don't fix it. Having said that,about a month ago we started to have ongoing issues with constant waking at night and only wanting a few fairy sucks before going back to sleep, after a week of that I was on emotional edge and starting to resent EVERYONE, I fed her (made sure she didn't fall asleep), walked around the house saying goodnight to everything, gave her her teddy and put her in her cot, she cried for 15 minutes then went to sleep, and has been going to sleep in her cot on her own for most sleeps ever since, and now she can do that, even when I feed her to sleep she no longer naps. DD2 was a lot older than your bub though so IMO understood what I wanted her to do in her cot, and we had the goodnight and teddy in place even when we used another means to put her to sleep before we tried just letting her cry for a while so it would be a gentle transition - but like I said, for me it was a cross the bridge when you come to it kind of thing, so feel things out if you want to try other means of getting bub to sleep, or if you want to wait a while. Good luck, in any case, I hope you get more sleep, we all know how desperate we can feel for it sometimes.
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