This was cute, but the scene with the makeup really bothered me, probably more than it reasonably should. It feels like she's telling the OL to just paper over the signs of her problems, so she'll present a more pleasant outward appearance for others, without really caring about or addressing the underlying causes; a bit like a guy telling a girl to smile because it makes her look pretty.
Obviously, in this case, it was just one interaction in a string of interactions and there's no real way a random high school girl could do anything to meaningfully help an unrelated adult working at a black company, so maybe it was more about helping the OL feel good about herself despite the sleep deprivation.
I don't know. Something about the way things were worded just rubs me the wrong way.