The Riddle Master Hits Middle Age

Well met, hale wanderer! You have journeyed through the Fiendish Greenwood, over the Sea of Knives, and across the Barren Plains of Evermore to reach the citadel ahead: the Academy of Arcane Knowledge!

Owing to my ragged cloak and even more ragged beard, you no doubt believe I am merely the town fool. But to enter the Academy and gain True Understanding, thou must first answer my Riddles Three! For I am the Riddle Master of this enchanted sanctuary!

Riddle the First: What walks on four legs in the morning, two legs at noon, and three legs in the evening?

“Man,” you surmise? For he crawls as a baby, walks as an adult, and uses a cane as an elder? Correct! Perhaps thou do possess the wisdom necessary to pass…

Riddle the Second: It has a bed but never sleeps. And the one that uses it never knows that he’s using it. Of what do I speak?

“A river,” you guess? You betray your befuddlement! The answer is “a casket”!… er—wait.

I think I said the first part of the riddle for “river”—the bed part—but the second part for “casket.” I did, didn’t I?

….

….

Shit. Fuck.

Fuck!

I want to say this has never happened before. But it has. I’m just not the man I once was.

Oh, do I have regrets. I didn’t set out to be a third-rate Riddle Master in some Podunk village. I wanted to be a famous, respected Riddle Director on the Glittering Coast! I knew when I started taking riddling classes years ago that it was a tough biz, but I really did think I could make something of myself. I even submitted a couple of riddle packets to the late-night riddling shows. But your career ends up taking whatever turns… My point is, you gotta live the life you have, not the one you dreamed of. But, by Glizzblarth’s Greatsword, I can’t even do the riddle thing well anymore!

Here’s a riddle I do remember: How come I’ve never had a serious relationship in my entire life? Maybe because I was so obsessed with trying to “make it”—whatever even means—that I pushed aside everyone who ever cared about me. My therapist says everyone is deserving of love, but if I feel like a failure all the time, how can I ask someone to love me? Stop trying to think of an answer, that was a rhetorical riddle.

I try to tell myself that being a provincial Riddle Master is actually not so bad, but I can’t make myself believe it. And I don’t even do that much riddling; we hardly get visitors, so I mostly just sit in my hut by myself all day, every day, waiting for something to change, I guess.

Also, who even likes riddles? Maybe in my twenties I was passionate about them, but now—especially when there’s, like, actual serious shit going down in the world—riddles feel pretty pointless.

You’re thinking, “Riddle Master, you’re not that old. You can pivot.” Sure, sure. But I’m not qualified to do anything else. I mean, maybe advertising. But ugh.

Look, I’m not going to bother with Riddle the Third. The answer would’ve been “nothing.” Here’s a pro tip: If you don’t know the answer to a riddle, just guess “nothing.” It’s a very common riddle solution. “Holes” also comes up a lot. And, right now, that’s me: A lot of nothing with a big hole inside.

I apologize for taking up your time, you can enter the Academy of Arcane Knowledge if thou desire. I’ll be out here, pondering the one riddle I could never answer: What the fuck is the point of it all?

Oh, and don’t worry about the Academy’s Lord Chancellor, he’s rude to everyone. He wanted to be a rock music journalist for a print magazine. Why he ever thought that was going to work out… now that’s a riddle.