I consider myself a fairly laid-back, self-confident person, but the tired comment makes me feel violent and hideous.
I, too, have very dark, very permanent circles around my very deep-set, shadowy eyes. I used to get the tired comment constantly and (I'm sure I've mentioned this here before!) when I was a teenager somebody asked me if my boyfriend beat me and ooohhh, that's stayed with me for a long time.
Don't ever say this to anyone, especially awkward teenage girls who are already in a constant panic about the way they look.
I've come to terms with so much about myself and am happier than I've ever been, but the dark circles are my last insecure holdout. I really feel that when I can cheerfully leave the house without a thick coating of concealer on my eyes will be the day I have achieved true inner peace.