Before I had kids, I always laughed at the funny stories from my friends about crazy toddler sleep routines. The menagerie of stuffed animals they sleep with, the incessant requests for drinks of water or “one more song,” and the stories of climbing out of cribs and escaping bedrooms. It all seemed so crazy and so silly, and I couldn’t fathom that all toddlers are actually that weird when it comes to sleeping.

Then, I had a toddler of my own.

Jackson, like most toddlers I know, has quite the assortment of “friends” he likes to sleep with. It’s constantly changing and he’s constantly adding to his collection. He makes up the silliest requests to get me to stay in the room just a few minutes longer at bedtime (the other day he said, “mama, I need to see your teeth!”), and if his sleeping environment isn’t exactly the way he likes it, the whole thing is shot.

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Currently, when Jackson goes to sleep he has:

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  • A knit blanket my grandmother made him
  • An Aden + Anais swaddle blanket
  • An Aden + Anais lovey
  • A stuffed Cookie Monster
  • A stuffed puppy
  • A teddy bear
  • A stuffed dinosaur
  • An elephant neck pillow (no idea how that found its way in there)
  • A stuffed dragon
  • A pacifier

He also asks for a book every night, but I’ve stopped allowing him to keep books in his bed because it seemed to be affecting how long it took before he went to sleep.

Our pre-sleeping routine is pretty simple – a few books, a song, and then we lay him down…and that’s when the shenanigans begin. Here’s what a typical night looks like:

– I lay Jackson down, he immediately throws his feet straight up in the air and starts giggling.

– I tell him to put his feet down. He ignores me. I tell him I’m just going to leave if he won’t listen. He finally puts his feet down.

– I put both blankets over him and tuck him in as tightly as I can. Then, I arrange the stuffed animals exactly how he likes them. Teddy bear on one side, dinosaur on the other, Cookie Monster and dragon on either side of his head and the puppy at the top of his head. The blanket gets tucked next to his face and the elephant pillow is usually just floating around the bed. If any of his friends are out of place, he will make sure you know about it.

– I give him a “big kiss” and a “tiny kiss” (he insists on both), and then start to leave. He hollers that he needs something – usually, it’s to be tucked in again because as soon as I turn my back he wiggles out. I’ll usually oblige him for the first request, then give another round of kisses. I try to leave again and he shouts “wait!” again…the requests often get strange from here on out. Sometimes it’s for a hug or another kiss, sometimes he wants me to pick him back up and sing again, and sometimes he starts asking to see my teeth or hold my necklace, or to get a different binky or a different blanket because his is “dirty.” After the second request, I usually tell him I’m done and leave.

– Depending on the night, he either goes straight to sleep or he shouts for us two or three more times before he actually sleeps. He hasn’t started climbing out of his crib yet (thank goodness), so Mr. Garland and I just tag team checking on him for the 20 or 30 minutes after we lay him down to make sure he’s settling and actually going to sleep.  At some point (usually pretty quickly), he finally gets quiet and we know he’s going to sleep.

At this point, we just roll our eyes and giggle at his bedtime antics…he never takes too terribly long to fall asleep at night, and we know that some day we won’t hear him calling for us to come into his room at night anymore so we cherish these silly little requests for extra love while they’re still coming.

Toddler bedtime routines and how complicated they can be is still a topic that confounds and amuses me to no end – it seems that the vast majority of toddlers have similar demands and issues when it comes to bedtime, and no one seems to have figured out the perfect solution for an easy bedtime yet. For now, we’ll just keep trucking along with how we’re doing things and hope that he doesn’t go off to college with 25 different stuffed animals to sleep with.

What does your toddler need in order to go to sleep?