Paintbrush didn't cry often. Well they DID cry, everyone does, it was rare that they did.. when they were upset, they usually just got so angry thay they blew their top. (Both literally and figuratively.

it wasn't until they watched the featureless bodies of all their previous friends and teammates hit the ground that they actually cried infront of other contestants.. all of their friends had died, been deleted from this world.. it was only them, Marshmallow, Apple and you left in the bright lights.

You and Paintbrush were currently sitting on the staircase of the purgatory mansion, with them leaning on your shoulder and you.. I guess- consoling them. (Trying at least, as they're a very emotional person.