This past week nighttime has been really hard. My Little One still falls asleep nursing. The transition to the crib for the past few nights has been extremely hard and takes many tries. Then he’s been waking frequently and begging to be in our bed. I’ve done it for the sake of my own sleep, but he is also sleeping poorly in there, tossing and turning and sitting up throughout the night. Is this an age thing? He’s 23-months.
— Sleepless

This is a great question — one that I asked myself a lot when my daughter was that age.
More importantly, I found that I had to ask myself why I was trying to make the night weaning/crib thing happen.
My honest answer was that I felt like it was what I was “supposed to do” even though it totally went against my gut to have so many tears + frustration during the night.
So, I stopped pushing it + we’re all sleeping better.
We have dinner, clean-up, give her a bath and put PJs on.
Then, we do a big nursing session while reading stories.
After, we brush teeth + put my daughter in the stroller (with a bunting: we’re in Boston + it still gets cold). Most nights, we walk the dogs + have a conversation as husband/wife while she falls asleep. Other nights, I stay behind to catch up on some housework or business.
It’s been so healthy for us!
Then, when we get home, we bring the stroller into our bedroom right up next to the bed, for a smooth transfer into our bed (make sure baby is limp wrist before moving).
She’s so deeply asleep that I’m able to get a solid block of like 4 hours of sleep minimum at the other side of the bed.
Alternatively, I can just walk right out of the room to have more adult time with my husband, and when she wakes later at night to nurse, I’m not as frustrated by it because I feel like I got a break.

Fast-Forward Update
When my daughter turned 2-years-old, she started having a few instances of sleeping through the night. It was like she had grown into the ability overnight one night.
I completely attribute that to our consistent routine + not changing our nursing helped her to settle herself back down happily + much faster.
Sarah Ockwell-Smith has a great book — The Gentle Sleep Book — that explains how just like walking + talking, sleep is a developmental milestone.
We can’t force sleeping like we can’t force walking + talking, and that really resonated with me. Maybe it will for you, too. ♥️
Wishing you some good sleep soon!
Courtney