Even though it's pretty close (2:10 hour cheap bus, 1:20 expensive amtrak, 2:30 decently priced commuter rail connection), I don't actually go to NYC all that much, and when I do I'm usually doing at least one touristy thing which requires me to go to Midtown in the general vicinity of Times Square (theatre, for example). I know all good New Yorkers stay away from such places, though I assume some of them also occasionally visit those theatres, but over the past few years it's become increasingly impossible to walk through that area. I don't mean in a "wah I'm old I don't like crowds" sense, I mean that on a typical weekend day/evening without any real special event going on, the sidewalks are so packed that it's incredibly difficult to just walk a block.
I'm no expert on the area, but the obvious solution is to take a car lane on some of the avenues and expand the sidewalk. This will likely never happen, even though it's clear that the number of pedestrians traversing these blocks over any period of time is far greater than the number of people being transported by cars over the same period, because cars, but it's quite amazing that the powers that be don't look at the situation and think, "yeah, we gotta do something about this..."