Riddle: “You’re trapped in a room with no windows and no doors, no escape. There’s nothing but a table and a mirror. How are you able to get out?”

Solution: Look in the mirror, and you see what you saw. Take the saw, cut the table in half. Two halves make a whole, jump through the (w)hole.

Context: “I think I heard this from either my older sister or my mom first. It was one of those things they told me to try and stump me because how was I supposed to know the wordplay? I remember getting really frustrated at it but then thinking it was brilliant and immediately telling a bunch of other people, feeling so smart because I knew the wordplay and they didn’t. It’s one of those riddles that’s less about the actual process of finding the answer, it comes down to whether you know the specific wordplay or not.”

Analysis: This is undoubtedly the most creative riddle I’ve heard in a long time. The majority of riddles I’ve heard are just overly vague descriptions of simple things, like an egg or a mountain, but this one is far more interesting. I struggle to think of how someone could solve it without first being clued into the wordplay. But instead of that detracting from the quality of the riddle, I think it adds to it. The unusual nature of the riddle is what captivated the informant and gave it such significance to them, only compounded by the fact that they initially heard it from a close family member.