"Are you -" Harry said, and then shut his mouth. On second thought, no he was NOT going to ask the painting whether it was fully conscious in the sense of being aware of its own awareness.
"I'm Harry Potter," said his mouth, more or less on autopilot. Also more or less automatically, Harry stuck out a hand towards the painting.
The woman in the painting looked down at Harry's hand and raised her eyebrows.
Slowly, the hand dropped back to Harry's side.
"Sorry," Harry said, "I'm sort of new here."
"So I perceive, young raven. Where are you trying to go?"
Harry hesitated. "I'm not really sure," he said.
"Then perhaps you are already there."
"Well, wherever I am trying to go, I don't think this is it..." Harry shut his mouth, aware of just how much he was sounding like an idiot. "Let me start over. I'm playing this game only I don't know what the rules are -" That didn't really work either, did it. "Okay, third try. I'm looking for opportunities to do good so I can score points, and all I have is this cryptic hint about how darkness is where the light needs to be, so I was trying to go down but I seem to keep going up instead..."
The old lady in the painting was looking at him rather sceptically.
Harry sighed. "My life tends to get a bit peculiar."
"Would it be fair to say that you don't know where you're going or why you're trying to get there?"
"Entirely fair."
The old lady nodded. "I'm not sure that being lost is your most important problem, young man."
"True, but unlike the more important problems, it's a problem I can understand how to solve and wow is this conversation turning into a metaphor for human existence, I didn't even realise that was happening until just now."
The lady eyed Harry appraisingly. "You are a fine young raven, aren't you? For a moment I was starting to wonder. Well then, as a general rule, if you keep on turning left, you're bound to keep going down."
That sounded strangely familiar but Harry couldn't recall where he'd heard it before. "Um... you seem like a very intelligent person. Or a picture of a very intelligent person... anyway, have you heard of a mysterious game where you can only play once, and they won't tell you the rules?"
"Life," said the lady at once. "That's one of the most obvious riddles I've ever heard."
Harry blinked. "No," he said slowly. "I mean I got an actual note and everything saying that I had to play the game but I wouldn't be told the rules, and someone is leaving me little slips of paper telling me how many points I've lost for violating the rules, like a minus two point penalty for wearing pyjamas. Do you know anyone here at Hogwarts who's crazy enough and powerful enough to do something like that? Besides Dumbledore, I mean?"
The picture of a lady sighed. "I'm only a picture, young man. I remember Hogwarts as it was - not Hogwarts as it is. All I can tell you is that if this were a riddle, the answer would be that the game is life, and that while we do not make all the rules ourselves, the one who awards or takes points is always you. If it is not riddle but reality - then I do not know."
Harry bowed very low to the picture. "Thank you, milady."
The lady curtseyed to him. "I wish I could say that I'll remember you with fondness," she said, "but I probably won't remember you at all. Farewell, Harry Potter."
He bowed again in reply, and started to climb down the nearest flight of stairs.
Four left turns later he found himself staring down a corridor that ended, abruptly, in a tumbled mound of large rocks - as if there had been a cave-in, only the surrounding walls and ceiling were intact and made of quite regular castle stones.
"All right," Harry said to the empty air, "I give up. I'm asking for another hint. How do I get to where I need to go?"
"A hint! A hint, you say?"
The excited voice came from a painting on the wall not far away, this one a portrait of a middle-aged man in the loudest pink robes that Harry had ever seen or even imagined. In the portrait he was wearing a droopy old pointed hat with a fish on it (not a drawing of a fish, mind, but a fish).
"Yes!" Harry said. "A hint! A hint, I say! Only not just any hint, I'm looking for a specific hint, it's for a game I'm playing -"
"Yes, yes! A hint for the game! You're Harry Potter, aren't you? I'm Cornelion Flubberwalt! I was told by Erin the Consort who was told by Lord Weaselnose who was told by, I forget really. But it was a message for me to give to you! For me! No one's cared about me in, I don't know how long, maybe ever, I've been stuck down here in this bloody useless old corridor - a hint! I have your hint! It will only cost you three points! Do you want it?"
"Yes! I want it!" Harry was aware that he probably ought to keep his sarcasm under control but he just couldn't seem to help himself.
"The darkness can be found between the green study rooms and McGonagall's Transfiguration class! That's the hint! And get a move on, you're slower than a sack of snails! Minus ten points for being slow! Now you have 61 points! That was the rest of the message!"
"Thank you," Harry said. He was really getting behind on the game here. "Um... I don't suppose you know where the message originally came from, do you?"
"It was spoken by a hollow voice that belled forth from a gap within the air itself, a gap that opened upon a fiery abyss! That's what they told me!"
Harry was no longer sure, at this point, whether this was the sort of thing he ought to be sceptical about, or the sort of thing he should just take in stride. "And how can I find the line between the green study rooms and Transfiguration class?"
"Just spin back around and go left, right, down, down, right, left, right, up, and left again, you'll be at the green study room and if you go in and walk straight out the opposite side you'll be on a big curvy corridor that goes to an intersection and on the right side of that intersection will be a long straight hallway that goes to the Transfiguration classroom!" The figure of the middle-aged man paused. "At least that's how it was when I was in Hogwarts. This is a Monday on an odd-numbered year, isn't it?"
"Pencil and mechanical paper," Harry said to his pouch. "Er, cancel that, paper and mechanical pencil." He looked up. "Could you repeat that?"
After getting lost another two times, Harry felt that he was beginning to understand the basic rule for navigating the ever-changing maze that was Hogwarts, namely, ask a painting for directions. If this reflected some sort of incredibly deep life lesson he couldn't figure out what it was.
The green study room was a surprisingly pleasant space with sunlight streaming in from windows of green-stained glass that showed dragons in calm, pastoral scenes. It had chairs that looked extremely comfortable, and tables that seemed very well-suited to studying in the company of one to three friends.
Harry couldn't actually walk straight through and out the door on the other side. There were bookshelves set into the wall, and he had to go over and read some of the titles, so as to not lose his claim to the Verres family name. But he did it quickly, mindful of the complaint about being slow, and then went out the other side.
He was walking down the "big curvy corridor" when he heard a young boy's voice cry out.
At times like this, Harry had an excuse to sprint all-out with no regards for saving energy or doing proper warmup exercises or worrying about crashing into things, a sudden frantic flight that nearly came to an equally sudden halt as he almost ran over a group of six first-year Hufflepuffs...
...who were huddled together, looking rather scared and like they desperately wanted to do something but couldn't figure out what, which probably had something to do with the group of five older Slytherins who seemed to be surrounding another young boy.