Ask Ugly: all of the ‘iffy’ comments about my gray hair bother me. Should I start dyeing it again?

I’m 53 (I started going gray in my 20s) and I like my face, but the comments from people I haven’t seen in a while can really derail my fragile conviction that my hair is – and I am – beautiful no matter the color. It made me realize how much I relied on outside feedback for confidence, which sucks, but is still a deep-rooted (pardon the pun) belief. One “Oh, but you looked so much younger/prettier/less tired when it was dark” from my son’s former baseball coach or a neighbor can really have me pondering a new dye job. It doesn’t help that I’m divorced with no dating prospects and have put on some weight.