Snow Day has worked very hard to master the art of teaching. (That's why he's a nanny. To teach all the little ones so they'll be wise when they grow up) He wishes to someday find someone to share his knowledge with that's his own age. I think he needs someone to show him that he's not the smartest bird in the sky.
Pretty much he needs a mate or a good friend to keep him in line. He likes to talk but would love to listen aswell. I think he'd enjoy someone who's the opposite of him. Someone crazy who prefers partying over hard work. Snow Day needs to find his more laid back,careless, and impulsive side.
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this hat is a must 
biting a small pair of glasses that she's holding in her right hand. 
Sitting with her legs crossed. Left elbow leaning on a pile of books.
maybe a ring on a feather like in this picture. That's actually pretty cool.