Day 1: Endless possibilities

Two Canadian penguins are paddling a canoe through a desert. The first one says, "Where's your paddle, eh?" The second one says, "sure does!"

Despite my disbelief, anger, confusion, linguistic proofs, and pleas for mercy, this monstrosity of an interaction is nevertheless said to have a grammatically correct interpretation. Do I believe this claim? To be honest, not really. Will I spend an exorbitant amount of time trying to figure it out anyways? Absolutely not. However, since this riddle has been plaguing my brain anyways, I may as well write down what on earth this could possibly mean.

Garden Path Sentences

My immediate instinct upon hearing this riddle was to assume that its grammatical quirks arose from incorrectly parsing the sentence. Similar to the garden path sentence "the horse raced past the barn fell", where the listener is tricked into believing that raced is the verb of the sentence, referring to the horse, and not the beginning of a four-word modifier, I naïvely thought that this riddle could be resolved by an alternative parsing of the words. However, all of the noun-verb agreements seem to be pretty convincing—the only potential thread seems to be "a canoe through a desert", where "through a desert" could, in theory, be a modifier referring to some other part of the sentence. However, this entire line of thought seems to be pretty fruitless, and I called the idea my brain thought of a failure.

Homophones

Out of all the hints I've gotten so far, one stood out above the others. When I decided to restate the riddle in my own words, substituting the word asks for the word says, someone immediately corrected me and pointed out that this is, in fact, the wrong sentence. Aha! thought I, perhaps the way the specific words sound have something to do with the riddle. This brought me to my first obvious idea:

Wears your paddle

Turns out, the where's-wears homophone turned out to be more solid than I expected, endowing me with my first grammatically correct solution to the puzzle:

Two Canadian penguins are paddling a canoe through a desert. The first one says, "Wears your paddle!" The second one says, "sure does!"

This interpretation assumes the presence of a third Canadian penguin, who is, undoubtedly, wearing the second penguin's paddle as part of a questionable fashion statement. The first penguin, upon seeing the third, says "[he] wears your paddle!" to the second. The second sure does agree with the first.

This interpretation is unconvincing in multiple ways. First, the entire phrase "wears your paddle" is awkwardly missing the subject of the sentence. The more nagging thought, however, is that this interpretation completely disregards the setup of the riddle—the desert, the canoe, the paddle. And the entire idea that a paddle is used as an article of clothing is, simply put, dumb. If this were to be the case, the riddle should've at least used a better verb-question homophone, like hears your paddle!, since that would at least somewhat relate to the paddle making noise as it hits the water. Wait, but aren't they in a desert? We'll definitely have to think about the setting later. For now, let's try another homophone:

Tupang Winsor

Tupang Winsor, a preppy young gentleman from the southern British Isles, heads out for a trip to the Sahara. But, he thinks, who will care that some English gentleman visits the Sahara desert? If I want to get into the history books, I'm going to have to break a record. Indeed, he decides to pursue this goal—he'll be the first person to cross the Sahara on a boat.

Tupang Winsor, paddling a canoe through the desert (the first one), says, "where's your paddle?" The second one says, "sure does!"

Here, the young Mr. Winsor, oar in hand, smiling, suddenly turns towards the camera, and asks you, the viewer: where's your paddle? why aren't you here, with me, enjoying this moment? Twenty years later, this feat is repeated by a second young gentleman, who, for some random-ass reason, decides to face the camera and say "sure does!". What could that even be a response to? "Does Red Bull give you the energy to cross the Sahara—in a boat?" No, no, no, this is all nonsense. God damn it.

Location

You know, let's go back to thinking about location for a moment. What can a desert contain? As we all know from the Earth Science game, stones. For the purposes of most puns, a desert contains sand. From a meteorological perspective, most deserts contain—ice. Wait a second! Penguins, ice, deserts? This all has to be pointing to Antarctica! Aha, so since they're in Antarctica, they're not doing anything out of the ordinary—just going about their daily tasks, visiting friends, catching fish. So maybe paddling refers simply to swimming! And, as we all know, where's your paddle is colloquial penguin for where are you paddling; in a broader sense, referring simply to where are you going? The second penguin could, you know, be off to a friend's house. Perhaps to a friend named Sherda. Perhaps this entire riddle just got solved:

Two penguins are paddling through the desert. The first one says, "where's your paddle?" The second one says, "Sherda's!"

Boom! That's it. No tricks, no games. Two penguins, swimming around, minutes from their home, are discussing their plans for the day. The first asks the second where he's off to. The second one's going to a friend's iceberg. There are zero issues with this—Sherda is a pretty popular name—and it's a nice, cozy story about two penguins just penguining around. I think it's perfect.