As a child of only five years old, and despite how his intelligence is starting to shine, he still is a child, after all. So seeing Kasuka’s blank expression triggers a normal reaction.
“Why do you look so sad?
Sadness isn’t good y’know!
People cry when they are sad,
and it makes me want to cry too!”

How strange, that a mini-Izaya would say that he looked sad. Kasuka didn’t think so - in fact, he thought he looked blank enough that that would be all he was considered. A blank slate. This was the first time he had been dubbed as sad.
”I’m not sad.
And you don’t have to cry.
There’s nothing to cry about.“