He (my colleague) was… walking home one day, from his office down in Bishop Hall… when he noticed this lady coming down the chapel steps. And… he goes in front of her and he can see that she has no face. It’s just… black (encircles face with hands), all black inside this cowl. And at that point he realizes that she’s not walking… she’s floating a few inches off the ground, and her left shoulder was up a little higher and she was just floating, floating until she floated right through that grating at Bishop.
I used to teach high school… and one of the kids in my AP (homeroom), he worked running the lights in Dillingham auditorium. And he’s looking over at the right side and he sees a shadow, but then he’s looking around for… well you know, he works with lights, so he knows where all the sources of light would be; how could a shadow be over there on that wall, when there’s no light source? And then he takes his light, and with his hands steers it over to shine it on the shadow, because it should just disappear, but what the shadow does, it kind of turns, like it’s facing him, stands up, and then walks down into a crack…
How did you come across this folklore: “This is a story that was told to me by a friend, another Punahou faculty member, and another story of a similar interaction from a former student that told me what happened to him.”
Punahou is a very old school, with some buildings well over a century old… and lots of eerie things are known to happen from time to time. In other more detailed versions of the story, the Grey Lady is supposed to be a spirit of a former Punahou faculty member who inhabits the school chapel and reveals herself to people on campus, usually at night and when they are alone. She usually just scares people, and doesn’t cause harm. One of the purposes of this legend is to make the Punahou community more exclusive–it’s a campus wide legend, she stays on campus, and typically is only seen by students, faculty, or staff of the school.