Comment by scott_s

Answer: yes, of course it's sometimes appropriate.

But if you're having a serious conversation with someone on the subject of privilege, and you're on the privileged side (and they're not), the likelihood of you accurately identifying when they should lighten up is so vanishingly small (I keep finding my blind spots in spite of years of being attentive to this kind of stuff...), and the chance that they might actually benefit from that sort of comment from you in that moment is so ridiculously tiny, that you're better off holding your tongue.

Let someone else guide them if they are indeed going too far (let's pretend you're right, for the point of discussion) -- someone who they can trust more, for example.

EDIT: just to add -- the problem with these situations is that your instincts (even usually-reliable instincts) are almost certainly wrong. You may be smarter & more articulate; you may be able to debate them into the ground without breaking a sweat; but if you're on the privileged side and they're not, you're probably still wrong in this discussion, and you're not going to help that situation at all by being articulately wrong.

Just speaking for myself -- and I'm on the "winning" side of almost every privilege imbalance I can think of -- but it is not really possible for someone like me to get an natural grasp of what I'm really gaining. I can't help but forget, much of the time. It's like walking through life in a world with frequent, deafening shrieking noises that are just above my range of hearing, but most of the people around me can at least some of them, and are constantly knocked off-balance, disturbed, upset.... I can argue persuasively that with good concentration habits, an occasional shrieking noise shouldn't affect your life much, but I've never heard it once; maybe an echo here or there, that's it.