The above photo, as you may know, is of Marilyn Monroe as the Girl in The Seven Year Itch (1955). Note Marilyn's high heels. Any Manhattan "woman" would tell you to avoid grates while wearing them.
I live in New York and these subway grates are on many sidewalks and every time I'm walking with one of my girlfriends, and I'm in my boy shoes, I make it a habit to look down at my girlfriend's shoes as we approach the grates. If she is wearing flats or a thick heel then I keep on walking. However, if I see that my girlfriend is wearing a thin heel I automatically walk on the other side of her so as to walk over the grate myself giving her the solid sidewalk.
I never think of myself as a gentleman but in these situations I know first hand what it's like to walk down a Manhattan sidewalk in heels. As a man who cross dresses I know that the last thing I want is to have my heel stuck in a grate. It's not glamorous!
They say chivalry is dead. Well, if men would only walk a few New York sidewalks in women's shoes they would understand how chivalry is not so much a treat but a deep understanding of the female experience.
Now here with some sassy sidewalk walking is the lovely Jordan Sparkes taking "One Step at a Time"