My mom got cancer when I was in the 7th grade. The chemo took her hair. Everyday she would put on a wig that she absolutely hated, it was hot, scratchy, a pain in the ass to style, but she put it on and went to work.
Then when she came out of remission 2 years later and the chemo again made her lose her hair she said fuck it and decided no wig this time. Saying something very similar to what Jada did. And the first time she went to work without her wig, a co-worker, just joking around, said she looked Mr Clean. She totally lost it and burst into tears.
When someone is going through something like that they may tell themselves and others that they're not going to be hurt or offended by someone saying something but that doesn't mean when they actually are insulted, even when someone is joking, it doesn't hurt like hell.