What makes a great riddle?

[Image courtesy of PNG Find.]

I have always suspected that riddles were our first experiments with puzzles and puzzly thinking. Long before crosswords, Sudoku, codebreaking, and magic squares, the potential for wordplay and outside-the-box thinking would have appealed to storytellers, teachers, philosophers, and other deep thinkers.

Who doesn’t enjoy unraveling a riddle, parsing the carefully constructed sentences for every hint and nuance lurking within, and then extracting that tiny purest nugget of a solution from the ether?

Riddles appeal to our love of story and adventure, of heroes with wits as sharp as their swords. Riddles are the domain of gatekeepers and tricksters, monsters and trap rooms from the best Dungeons & Dragons quests.

And so, for centuries upon centuries, even up to the modern day, riddles have been a challenging and intriguing part of the world of puzzling.

We can trace them back to the Greeks, to Ancient Sumeria, to the Bible through Samson, and to mythology through the Sphinx. Riddles abound in literature; we find riddles in Shakespeare, in the works of Joyce, Carroll, and Austen, all the way up to the modern day with The Hobbit and Harry Potter. Every locked room mystery and impossible crime is a riddle to be unraveled.

[Image courtesy of Campbell County Public Library.]

But this raises a crucial question: what makes a good riddle?

At first glance, it should be confusing or elusive. But after some thought, there should be enough information within the riddle to provide a solution, either through wordplay/punnery OR through looking at the problem from a different perspective.

Let’s look at an example. In this instance, we’ll examine the riddle from Jane Austen’s Emma, which is posed to the title character by a potential suitor:

My first displays the wealth and pomp of kings,
Lords of the earth! their luxury and ease.
Another view of man, my second brings,
Behold him there, the monarch of the seas!

The answer is “courtship.”

The first half of the riddle refers to the playground of royalty — court — and the second half to the domain of her suitor — ship — and when combined they form the suitor’s desire. This riddle is confusingly worded, to be sure, but it makes sense when analyzed and it’s totally reasonable when the clever Emma figures out the answer… and turns down the suitor’s attempt at riddly courtship.

[Image courtesy of Yale.edu.]

So, what’s an example of a bad riddle? Well, unfortunately, we don’t have to look too hard for an example of one. Let’s examine Samson’s riddle from The Book of Judges in the Old Testament, which he poses to his dinner guests (with a wager attached):

Out of the eater,
something to eat;
out of the strong,
something sweet.

The answer, bafflingly, is “bees making a honeycomb inside the carcass of a lion.”

This is borderline nonsense unless Samson actually told you the story of killing a lion with his bare hands and later returning to the corpse to find bees building a hive inside. So, basically, this riddle not only screws over his dinner guests — who lost a wager to buy fine clothing if they couldn’t solve the rigged riddle — and serves as an excuse to brag about killing a lion. Samson is a jerk.

This is a bad riddle, because it’s designed to be confusing, but does not offer enough information to get to the desired solution. It’s purposely unsolvable, and that sucks. Riddles shouldn’t be arbitrary or nonsensical.

James Joyce pulled this in Ulysses. Lewis Carroll pulled it in Alice’s Adventures in Wonderland. And each of these examples give riddles a bad name. (Even if they do serve a literary purpose, as scholars claim they do in the Joyce and Carroll examples.)

Even if you want the hero to seem (or be) smarter than the reader, the riddle should still make sense. When confronted with five riddles by Gollum in The Hobbit, Bilbo Baggins solves four of them (and answers the fifth through charmingly dumb luck). It doesn’t hurt his character or make the reader feel like they’re being cheated when these riddles are resolved.

That’s another quality of a great riddle. Even if you don’t solve it, when you DO find the answer, it should feel like you were outwitted and you learned something, not that you were involved in a rigged game.

Oh, and speaking of learning, that reminds me of another example of a challenging yet fair riddle, one that comes from Ancient Sumeria (now, modern-day Iraq):

There is a house. One enters it blind and comes out seeing. What is it?

The answer, as you might have puzzled out, is “a school.”

Riddles can be devious or tricky; they can rely on misdirection, our own assumptions and biases, or careful word choice to befuddle the reader. But they should always be learning experiences, like the house you enter blind and leave seeing.

What are some of your favorite riddles, fellow puzzlers? Let us know in the comments section below. We’d love to hear from you!

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A Cornucopia of Clever Clues


Last month, in the afterglow of the Crossword Tournament From Your Couch event, I waxed nostalgic about some of the clever and tricky cluing that the constructors employed to keep the solvers on their toes.

I had so much fun poring over those puzzles and highlighting the clues that caught my eye that I’ve decided to do it again.

You see, I keep track of favorite clues from constructors as I solve various crosswords. Not only are they often witty, hilarious, and/or impressive, but they inspire me as a puzzler to always try to find entertaining, engaging new angles for clues.

So here are some favorites from my personal clue vault.

(And I’m crediting the constructor listed on the byline for each clue. These clues may have been created elsewhere and reused, created by the constructor, or changed by an editor, I have no way of knowing. So I’m just doing my best to give credit where credit is due.)

I’m a sucker for delicious wordplay, and thanks to a plethora of ingenious constructors, modern crosswords are rarely lacking in linguistic legerdemain.

One of my favorite cluing tropes is the old word-form switcheroo, when a constructor makes you think the clue is one word form (a verb, for instance) when it’s really a noun, or vice versa.

Erik Agard’s clue “Leaves from a club” certainly sounds like a verb, so it’s a fun surprise when you realize the answer is LETTUCE.

Similarly, the ability to utilize the multiple meanings of words can make for some seriously elusive clues. Mike Shenk’s “Volume setting?” has you thinking music or audio, but the answer SHELF also fits neatly.

Byron Walden is a master at this sort of cluing, as evidenced by his clue “Uruguayan uncle?” for the phrase NO MAS. Given how often TIO, TIA, MADRE, and other Spanish familial terms are used in crosswords, it’s a keen example of misdirection.


And playing with the tropes of crossword cluing creates opportunities for more wordplay.

“Trick or treat,” a clue from Aimee Lucido, masquerades as the common Halloween phrase when it’s really two examples cluing the answer VERB.

Similarly, “Jets or chargers starter” sounds like a sports reference, but the lowercase “chargers” reveals something else is afoot. The answer to this clue (which appeared in a puzzle constructed by Craig Mazan and Jeff Chen) is TURBO.

Erin Rhode’s “Drum, for some” sounds like a simple example-style clue, but the answer RHYME reveals how she hid her wordplay in plain sight.

Yes, these clues have a lot in common with wordplay clues, but they also play with the conventions of crossword cluing.


Oh, and speaking of clues that hide their trickery in plain sight, I’ve got a few examples of that as well.

Kathy Weinberg once clued ROWS as “15 things in this puzzle,” which is the sort of clue that’s simultaneously so vague and so on-the-nose that it drives me insane.

Similarly, Steve Faiella uses modern slang to hide an answer in plain sight with the clue “Has beef with somebody, say.” That sure sounds like a vernacular use of “has beef with,” so you’re less likely to read the clue as a simple description of EATS, the actual answer. Very sly.

I’m going to close out today’s post with a clue that’s not only clever, it’s economical as well. Robyn Weintraub clued HOLE with two simple words — “Darn it!” — and it’s as hilarious as it is effective.

What are some of your favorite crossword clues, fellow puzzlers and PuzzleNationers? Let us know in the comments section below! We’d love to hear from you.

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Putting Clever Cluing to the Test?


As a puzzler, there are few article titles that serve as more efficient clickbait than “6 CHALLENGING CROSSWORD PUZZLE CLUES THAT WILL LEAVE YOU CLUELESS,” so when I saw that title, fellow puzzlers, you know I clicked.

This article by the crew at Wealth Words claims to offer “the trickiest clues that have ever existed.” That is quite a bold statement. Shall we try our luck and see how we do?

Now, before we start, it’s worth noting that we’re at a huge disadvantage here, because any clue, easy or tough, can be made easier if you know some of the letters in the word thanks to words in the grid you’ve already placed that cross this particular entry. We don’t have any of those helper letters, so we’re going to have to rely solely on our sharp wits, wordplay skills, and love of punnery.

Okay, let’s get to it.

Clue #1: Leaning column? (9 letters)

Most crossword fans know that a question mark virtually always means there’s wordplay afoot, so you know you can’t take this clue at face value, which means anything relating to Pisa is probably out. If you focus on “leaning,” that could take you anywhere from Jenga to drunkenness, so let’s play with “column.” Other columns appear in graphs, Excel files, and newspapers.

A-ha. Newspaper column. And some of those “lean” to either the left or the right, depending on the author. This train of thought leads us to the intended answer OPED PIECE.

Grade: A- (It’s a solid clue where the answer doesn’t necessarily immediately jump out at you, but makes total sense once you’ve puzzled it out.)

Clue #2: Strips in a club (5 letters)

[Now, to be fair, “club” was capitalized in the clue on the webpage, but I felt like that was misleading, so I fixed it here. After all, capitalization can be used to great effect in crafty cluing — particularly if you conceal the capital word by making it the first word in the clue, which is always capitalized regardless — but here, it becomes an unnecessary red herring.]

This one is slightly harder, because you don’t immediately get the hint that there’s wordplay involved, since there’s no question mark.

This is one of my favorite kinds of clever cluing, the sort where our preconceived notions of word forms works against us. (Also, it sounds naughty, but isn’t, which I also quite enjoy.) At first glance here, the phrasing makes it sound like “strips” is a verb, when it’s really a plural noun.

And once you get into that mindset, you realize that we’re not talking about that kind of club, and the intended answer emerges: BACON.

Grade: A (Misdirection plus a tongue-in-cheek bit of lewdness? Great stuff.)

Clue #3: Group of crows (6 letters)

I have no idea how this one made it onto the list. Anyone who knows their animal groupings knows that a group of crows is a MURDER. There’s no tricky cluing or misdirection here, just something that might not be in the common knowledge. (But again, I think people are more likely to come up with this one that “exaltation of larks,” “smack of jellyfish,” or “parliament of owls.”)

Grade: D- (Could be difficult for some solvers, but only for unfamiliarity, not style.)

Clue #4: “Yep, perfectly clear” (7 letters)

Okay, this one has quotations around it, which both means it’s a spoken line and it’s likely non-standard, so you won’t find it in a dictionary. It’s probably a phrase, and used in casual conversation.

The answer, as it turns out, is I HEAR YA, which I don’t think any solver would come up with unless they had a few crossing letters filled in for them. The slangy spelling of YA and the informal wording altogether pretty much precludes this from being a “see-it-and-get-it” sorta clue.

Grade: C

Clue #5: [Boo-Hoo] (5 letters)

Brackets are used less commonly than quotation marks or question marks in crossword clue, so it’s more likely that a casual solver wouldn’t immediately recognize what to do with this clue. Usually, brackets indicate this is a non-traditional clue, either making an oblique reference to something or indicating it’s a non-verbal clue like a cough.

In this case, this is meant to be the actual sound of someone crying or something of that nature. So it could be something informal like CRYIN’ or TEARS (as opposed to the more traditional “in tears”) or something like that.

As it turns out, they were looking for I’M SAD. Which is pretty blah. It’s not a standard phrase, and comes off as a cheaply constructed way out of a bad corner, not a solid bit of fill to keep the puzzle interesting.

Grade: F

Clue #6: They come in last (3 letters)

This clue is fairly tough, because it’s both vaguely worded and has a curious letter count. It’s plural phrasing (with “they”), so that immediately makes you want to tack an S onto the end of the word. But it’s also such a short entry that a two-letter word plus S doesn’t seem to fit the clue.

So what comes in last? “End” would fit, if not for the plural phrasing. “P.S.” comes in last, but “P.S.’S” is really clunky, and I don’t recall ever seeing that pluralized.

So what were they looking for? XYZ. Ah. Alphabet entries. You’ll usually see entries like this centering around the first three letters (ABC) or a random string (“RST” seems to come up more often than most), and XYZ certainly fits the bill. But, in the end, it’s not a real entry, and it feels a little cheap, despite the decent wordplay involved in the cluing.

Grade: C-

So, what did I think of the Wealth Words “6 CHALLENGING CROSSWORD PUZZLE CLUES THAT WILL LEAVE YOU CLUELESS” challenge?

I thought it started off very strong with two clever, slippery clues that required you to play with the words and come at them from several angles before stumbling upon the correct solution, and I quite enjoyed those clues.

But the quiz took a real nose dive in quality starting with Clue #3, which had no wordplay at all. #4 and #5 relied heavily on being slangy non-standard verbiage rather than adept cluing or creative fill, and #6 was a bit of a cop-out, even if the cluing quality rebounded nicely.

All in all, I thought the specious entries outweighed the clever cluing on display early on, making for an underwhelming set of clues.

Final grade: C+.

What did you think of these group of challenging clues, fellow puzzlers and PuzzleNationers? Did you enjoy them or find them wanting? Let us know in the comment section below, we’d love to hear from you!

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PuzzleNation Product Review: Schrodinger’s Cats

Even if you don’t know the science behind it, you’ve probably heard of Schrodinger’s cat at some point in your life. If you haven’t, let me give you the short short version: there’s a box with a cat in it, and a substance that may or may not release inside the box and kill the cat.

So until you open the box, there’s no way of knowing whether the cat is alive or not. Schrodinger posited that, since we can’t know which is the case, both are true until the box is opened. It’s essentially a thought experiment which delves far deeper into quantum mechanics and particle physics than I’m going to in this review.

But the idea that someone created a card game based on the concept of Schrodinger’s cat is not only audacious, but pretty impressive. (And the puns are just the icing on the cake.)

[Some of the cat physicists in the game: Sir Isaac Mewton,
Sally Prride, Madame Purrie, and Neil deGrasse Tabby.]

Schrodinger’s Cats was funded through a Kickstarter campaign last year, and it’s the brainchild of Heather Wilson, Heather O’Neill, and Chris O’Neill. A mix of bluffing, deduction, and wagering, this game combines Name That Tune-style bravado and strategy with Poker-style game play.

Each player is a cat scientist forming hypotheses on how many boxes contain live cats, dead cats, or nothing at all. (While Schrodinger is away, of course. As the old saying goes, when the scientist’s away, the cats will play. Or something like that.)

Every player receives one box card for each player in the game (so if there are three players in the game, each player receives three box cards), as well as one cat scientist card.

Once the cards are dealt, players look at their box cards and see what each box contains, hiding this info from the other players. Then the players begin hypothesizing. They wager on how many of each result are in ALL of the boxes on the board. So, in the game layout above, there are nine boxes, and each scientist has to wager what’s in all the boxes.

But instead of starting with a high guess and then wagering lower totals (as you would in Name That Tune), you start low in Schrodinger’s Cats and wager upward. Scientists can also affect the wagering by “showing findings” — revealing one or all of their own boxes to either prove their hypothesis or make the other players doubt their own — or by swapping out some boxes. (Each cat scientist card also allows for a one-time-use special action for a player, which can also prove useful.)

When a player either refuses to wager higher or challenges another player’s hypothesis by yelling “Prove it!”, all of the boxes are revealed and the hypothesis is proven or debunked (meaning the player stays in the game or leaves). After multiple experiments (rounds of play), one character remains and wins the game (and an honorary doctorate from Cat Tech University).

What I enjoyed most about this game (other than all the pseudo-scientific jargon involved in playing the game) was the wagering, bluffing, and reading of opponents that is integral to the game play. With so few possible cards to reveal (only four, in varying quantities, as opposed to 13 different cards across four suits in poker), it’s not nearly as challenging as the classic card game, but offers a lot of similar game mechanics.

It’s great fun to try to outwit or read your fellow players in order to make the best hypothesis, and that’s a sort of puzzling that is often left behind in puzzle games. Often, you’re so busy trying to achieve a certain goal or acquire points that you stop actively interacting with the other players; but in Schrodinger’s Cats, a lot of puzzling and game play takes place in the actions and reactions of the other players. It’s a delightfully social game.

Although you can play with as few players as two or as many as six, I recommend playing with at least four characters to keep the game moving and interesting. Between raising hypotheses, showing findings, and trying to puzzle out what your fellow players are hiding, the more uncertainty you can introduce to the game, the better.

Schrodinger’s Cats is available from 9th Level Games and can be found here.

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PuzzleNation Product Review: Scrimish

The best card games are simple. People love War and Poker and Hearts and Go Fish because, at their core, they’re games you can learn quickly and play endlessly. There are no long tutorials or play-throughs, so you can learn all the complexities and rules with ease.

It’s difficult to find puzzly card games that are as accessible and replayable. Scrimish, a card game created by Danny Zondervan and recently funded through Kickstarter, fits the bill nicely. The rules are simple, but the strategy in the actual game is what gives Scrimish major replay value.

[On a very festive battlefield, I’ve finished setting up my cards
(bottom of the frame), while my opponent is still working on hers.]

Scrimish is an elegant mix of War, Chess, and Memory.

Each player gets a set of 25 cards, arranging them into five piles of five cards each, face down. The goal? Find your opponent’s crown card before they find yours.

Then you take turns drawing a card from the top of one of your piles and attacking the top card of one of your opponent’s piles in a one-on-one battle. Here’s where the War aspects begin. You see, each card has a number value, and the higher number wins. The losing card is discarded, and the winning card goes back to whatever pile it came from.

So in every encounter, both players learn something, because even if you lost that attack, you’ve learned the value of one of the cards on top of one of your opponent’s piles.

That’s where the Memory aspect comes in, because you have to remember what cards of your opponent’s you’ve seen. (You can check your top cards or your piles as often as you and your opponent see fit.) Then you can plan other moves and try to uncover their crown card.

You’ve got shield cards to defend with, archer cards to attack with, numbered weapon cards to battle with, and one crown card to defend. So, essentially, you’re playing a miniature game of chess with your opponent, except your pieces are hidden from them.

And that’s what makes for such a satisfying playing experience. You’ve got all sorts of strategy going on, plus chances for misdirection in both your attacks and your placement of cards at the beginning of the game. Do you go out heavy with high numbered cards early, or do you test their defenses with low cards? Do you arrange attack stacks and defensive stacks, or do your spread your resources out across all five stacks?

Plus, every card you attack with is one less you have in your stacks. So you’ve got a resource management aspect as well. All of this gameplay and puzzly potential, with fewer cards than your standard poker deck.

It takes only a few minutes to learn, but all the thought that goes into it makes every game of Scrimish feel fresh and new.

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5 Questions with Magician and Puzzle Constructor David Kwong

Welcome to another edition of PuzzleNation Blog’s interview feature, 5 Questions!

We’re reaching out to puzzle constructors, video game writers and designers, writers, filmmakers, and puzzle enthusiasts from all walks of life, talking to people who make puzzles and people who enjoy them in the hopes of exploring the puzzle community as a whole.

And I’m excited to have David Kwong as our latest 5 Questions interviewee!

Puzzlers by nature play with words, but none quite like David Kwong, a top-flight puzzle constructor and magician. Adept at sleight of hand and wielding a flair for puzzle constructing that makes me very jealous, David crafts illusions and puzzle grids with equal deftness, often doing so in front of a live audience!

In addition to his own creative endeavors, David serves as a magic consultant for film and television, and has contributed to The Mindy Project, The Incredible Burt Wonderstone, and most notably, the magic-infused heist thriller Now You See Me.

David was gracious enough to take some time out to talk to us, so without further ado, let’s get to the interview!

5 Questions for David Kwong

1.) How did you get started with puzzles?

My mother and I always bonded over being word-nerds. When I was a child, we would play Scrabble and solve crosswords. After college, I began writing crosswords with my friend Kevan Choset (I suppose I was jealous of his James Bond themed puzzle). Our first puzzle was the April Fool’s Day puzzle in 2006. I think we waited three years for it to get published!

[Glenn’s note: The James Bond puzzle refers to one of Choset’s earliest, where “007” not only appeared in the grid, but crossed “SEAN CONNERY.” The April Fool’s Day puzzle refers to a Choset/Kwong collaboration that actually required the solvers to write the word “THINK” outside the box (grid) four times.]

2.) Magic and crosswords might seem like separate enterprises, but they both involve a whimsical sense of playing with your audience’s expectations (magic with misdirection, crosswords with clever cluing and wordplay). What about magic and puzzles so appeals to you?

You nailed it. Magic and crosswords both involve misdirection, surprises and toying with conventions. Take for example if I were to vanish a coin, I would place it in my hand three or four times plainly before secretly feigning its placement on the fifth time. Magicians allow their audiences to become familiar with what is “normal” so that the “abnormal” goes undetected (or rather looks the same).

A crossword that toys with the rules of the puzzle operates much in the same way. The constructor leads solvers down a path of what seemingly looks like a normal puzzle, and then suddenly hits them with a twist.

(Check out this short video, which highlights David’s whimsical fusion of magic and crosswords.)

3.) What types of puzzles and feats of magic are your favorites or have most inspired you?

I love puzzles in which the twist hinges on the everyday words and phrases that we’ve come to expect as solvers. Ashish Vengsarkar had a great puzzle in which “Start of Quote” and “Part 2 of Quote” were revealed to be BRITISH WAITING LINE and SECOND PERSON SINGULAR.

Also, I know it’s been referenced a million times, but the BOB DOLE / CLINTON puzzle is the ultimate example of misdirection in a crossword. There’s no better way to misdirect your audience before the final reveal than to have them think the trick is over!

[Glenn’s note: David is referencing the famous New York Times puzzle that appeared the day before the 1996 presidential election, a puzzle that famously offered either “BOB DOLE ELECTED” OR “CLINTON ELECTED” as an answer depending on how the solver filled in the grid.]

My favorite magic tricks are the ones in which the subterfuge is taking place right under the spectators’ noses. As performers, we call these “bold” moves and take a particular delight in executing them effectively. Often this means no intricate contraptions, no smoke and mirrors — just a strong ability to misdirect. There’s a routine called “card under the glass,” which illustrates this concept. The performer declares, “I will again and again place your card underneath this glass. See if you can catch me.”

And the audience never stands a chance.

4.) What’s next for David Kwong?

“Now You See Me” was such a big hit that we’re making a sequel. There are a number of Houdini projects in the works as well. I’ve also consulted recently on “The Imitation Game,” which is the story of Alan Turing and Bletchley Park cracking the German enigma cipher machine. There’s a great line in that script: “[Alan,] you just defeated Nazism with a crossword puzzle.”

5.) If you could give the readers, writers, puzzle fans, and magic lovers in the audience one piece of advice, what would it be?

Magic and puzzles are both forms of storytelling. If you’re creating magic tricks or constructing puzzles, think about how you can take your audience on a journey, even if just for a few minutes. Play into their expectations and hit them with twists and turns.

Finally, look for fresh combinations of seemingly unrelated things. You might be surprised that their cross-pollination can yield something innovative and original. Who would have thought that magic and puzzles could be synthesized?!

Many thanks to David for his time. You can learn more about David and his ever-expanding filmography on his website, DavidKwongMagic.com, and be sure to follow him on Twitter (@davidkwong) and Facebook (facebook.com/dkwongmagic) to see more of his mystifying exploits.

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