Bedtime used to involve a very predictable cast of characters: Brown Bear, White Bear, Orange Bear, Blue Bear (with Car Bear), and White Blanket, all stuffed in the corner of Ryan's bed next to his pillow. Later, three moose joined this pile, with Gregory the moose placed at the bottom of the pillow, right under Ryan's neck. It was a finite, manageable list - check off all these items, and we're ready for bed.
All bets are off now.
Ryan has been experimenting with selecting new and novel friends to bring to bed each night. I'd understand if he chose soft, comfy things to sleep with, but Ryan's choices tend to be hard, pointy, or just plain weird. Recent bedtime companions have included a variety of plastic animals (horses, elephants, a lobster), foam snowman stickers, toy trains, a figurine of a knight with a sword, and a plastic ear of corn.
I think this grew out of a trick we developed to get Ryan to transition from playing to brushing his teeth. We would ask him "Whose teeth should we brush tonight?" and he would select a toy, bring it to the bathroom, and brush its teeth (or face, or whatever - most of his toys of choice don't actually have teeth). While Ryan would brush the toy, I would start on Ryan's teeth.
This worked perfectly for a while. Then it got weird.
Ryan started gathering two toys to brush. Then three. Then seven. Then when he was done brushing them he would have to line them all up on the sink counter while he went about his business. I would then have to scoop up all the toys so they wouldn't distract him or fall into the toilet.
Then Ryan figured out the logical next step: once the animal (or corn, or Connect Four box*) had brushed its teeth, it was time for it to get into bed. And not in the corner next to the pillow like a common teddy bear: one who brushes his teeth gets to sleep on top of the pillow, or in the middle of the bed, right under Ryan.
There's a certain logic to all of this. But it looks really uncomfortable to sleep on top of a plastic giraffe.
* I wish I was kidding about this one.