One of the most challenging parts of making a puzzle is coming up with new or clever clues. I daresay it’s the toughest part of creating a puzzle.

Of course, that same challenge also makes it one of the most enjoyable aspects of both puzzle-making and puzzle-solving. (After all, if every clue is simply a synonym or a fill-in-the-blank, it wouldn’t be much of a puzzle.)

Now, I love wordplay, I always have. Whenever I can work palindromes or anagrams or the like into a puzzle or its clues, I’m all over it. Getting to do a series of Tom Swifties as clues one time was a particular joy.

But this style of cluing is harder than you think, since sometimes you only have so much space allotted for cluing an entire puzzle. The difference between two lines and three can be crucial.

So your goal should be wordplay that’s funny AND space-efficient while still being appropriate for a wide audience. A personal favorite that I’ve seen in crosswords for a while now is the clue “It’s for posers.” (The answer is “yoga.”)

In my own cluing experience, my sense of humor occasionally causes me to stray toward impropriety when it comes to clues.

For instance, I had a puzzle where I needed to clue “bald,” so I used “unlocked” as the clue. Mildly clever, not too bad, and totally unoffensive. That’s the trinity I need to hit for new cluing.

But in the same puzzle, I had the word Lisp, and I was trying to conjure up a fun clue, instead of relying on something like “speech issue,” which is bland. The clue I eventually came up with — “Make sin thin, e.g.” — made me smile, but I scrapped it, because it might come off as insensitive.

That’s why a clue like “Grass guillotine” for “lawnmower” could cause some problems. You could offend people with that. (The French, or the recently decapitated, I suppose.)

But sometimes, you simply can’t help yourself. A fellow puzzler was trying to come up with an inoffensive way to clue “witch hunt,” a phrase that would’ve fit nicely into a particular crossword grid. (Referring to either the historical pursuit of witches OR the general connotation of persecution was out of the question.)

My thought was that wordplay could save the entry, by getting people to summon up the phrase itself without the negative connotations. You know, like “spellcaster’s search?” or something like that.

That clue came to mind later. After another clue. One that I loved so very, very much, but that I could never use for the above reasons.

My clue for “witch hunt”…

“Pressing engagement.”