The Distinction Dossier: A Puzzling Problem

Dilemma, predicament, quandary, and conundrum all describe certain spots of bother. As we shouldn’t, however, like a pizza deliveryman to arrive where we need armed police, it is best that we use our language to distinguish problems accurately, the former being those of mild hunger and a hulking and aggressive home-intruder, respectively. 

Dilemma, predicament, and quandary are words that comprise a group of words that describe complicated, perplexing situations from which one would have a difficult moment or two disentangling oneself. They also, however, have discreet meanings, which have a kind of  loosely linked logical crescendo of unfortunate events.

Dilemma, for your average Cretan, describes any difficult situation, but dilemma’s true meaning is to describe two possibilities in which one faces a choice between equally undesirable alternatives, something of a “damned if you do and damned if you don’t” sort of pinch. The Prisoner’s Dilemma is a popular one that intellectuals enjoy casually dropping into dinner conversation, hoping that the eyebrows of members of the opposite sex find the topic interesting.

Pictures might aid the visually inclined.

Here we see the classic dog-faced-man/man-faced-dog rump-chewing choice.

Dilemma is pre-predicament, as it is assumed that, prior to the dilemma at hand, things were popping along sans rump-chewing.

But now we are in a predicament: a difficult situation that is especially unpleasant or unfortunate. Predicaments might be best understood as “currently having a rough go.” Some warm-blooded people call these “jam ups.”

Here no choice is to be made. You’re going for a swim. This is merely a tough spot.

Quandary: A state of uncertainty or confusion that renders one unable to act, which is often accompanied by puzzled, doubtful, and uncertain feelings. Affecting anyone from lovers to lummoxes, quandaries span the situational gamut. 

Here we see James Herriot in a quandary. To help Tristan would be to honor a friend–and recidivist–whilst the opposing action would honor the professional relation with his boss, Sigfried, thoroughly frying Tristan, but, perhaps simultaneously beginning Tristan’s recovery from alcohol-induced fun-having, which is what a good friend does. James rightly falters in his step.

A conundrum, however, has its own category. A conundrum specifically denotes a complicated, perplexing question or problem, not situation. A conundrum manifests as a riddle or puzzle, the answer to which often involves a pun or play on words, though it can also be purely a logical conundrum. Ironically, unlike the rest of the words on this list, conundrum’s etymology is unknown, though sources such as Fowler and the OED suggest its origins in 16^th-century Oxford or Cambridge as a pseudo-Latin joke, like hocus-pocus. 

Here we see the kind of conundrum that keeps me up nights, but the likes of which are solved daily by schoolchildren in Russia.

The proper definition of conundrum.

All tight spots, to be sure.