I hear that question more often near the trailhead, not so much in the backcountry. Mostly asked by less experienced hikers who have set out to hike to "the lake", "the waterfall", etc., and are feeling tired out and wondering whether to keep pushing on or turn around. I don't begrudge them whatever info I am able to provide, vague as it may be ("I passed it an hour or two ago"). Not everybody has had the opportunity to be trained in the ways of the outdoors by scouting, NOLS, parents, friends, etc. For those who are doing this without any background, a mile is a very nebulous concept! It takes experience to "get" it, and if someone as experienced as WD still works at judging time and distance, how much harder must it be for those babes in the woods?

I agree with the concept of trying to treat everyone as I would like to be treated. I like to think that with encouragement ("yeah, it's another hour or so, but it's really beautiful up there!"), some of these people will go on to have more positive experiences in the outdoors and maybe end up being the ones answering questions one day. Sure, there are the dopes that just won't ever get it, but I am not interested in deciding which people "deserve" an answer and which don't.