Our collective sense of irony, it seems, has never been in better health. We say, “How ironic!” as a politician’s hypocrisy is exposed; we laugh knowingly as Sacha Baron Cohen’s alter egos eviscerate their prey with perfect Socratic irony; we feel keenly the dramatic irony as Romeo takes his own life, thinking Juliet has killed herself. Irony, in all its forms, pervades our lives.

And yet, as soon as we move from being appreciative connoisseurs to active purveyors of irony, we run into difficulty. Verbal irony – the ostensibly simple act of stating something that is not meant – is a fragile thing, a contract between ironist and audience that is easily broken. Without mutual understanding, a theoretically ironic statement just does not work: a veiled compliment is mistaken for the insult behind which it is hidden, while an ironic expression of praise loses its critical sting. Sometimes, most simply, a meaningful statement becomes nonsensical.

Spoken irony, for the most part, avoids such pitfalls by virtue of tone of voice and the body language with which we accompany it. By cocking an eyebrow, by feigning enthusiasm or boredom, we give an attentive listener the clues they need to extract our true meaning. The problems most often arise not when we utter an ironic statement but when we try to write it down.

Yet written language is not without its own body language of sorts in the form of punctuation, and to approximate a specific tone of voice we might employ italic or bold text. Despite this, writers persist in looking for alternative ways to signal irony. For evidence of this we need look no further than the prevalence of the “smileys” with which we decorate jokes sent over SMS, instant messaging and email. Plainly, we do not trust conventional marks alone to convey our meaning. Even a crude :-) or ;-) is preferable to having an ironic comment misunderstood by its reader.

The difficulty of signalling textual irony was first documented in the 16th century, when in 1509 the Dutch humanist Desiderius Erasmus bemoaned the lack of a mark with which ironic statements could be punctuated. Erasmus declined to address the problem himself, and it was not until 1668, in Restoration England, that the first true irony mark was minted. It came from the versatile mind of the Reverend John Wilkins, a clergyman, natural philosopher and minor da Vinci of his day.

Living through the English civil war and the restoration of the monarchy that followed it, Wilkins no doubt had a firm grasp of the concept of irony. Having once served as chaplain to the nephew of King Charles I, he married a sister of the Royalists’ bête noire, Oliver Cromwell, who installed him as head of Trinity College, Cambridge; he lost the post on the Restoration but contrived to become the first secretary of the newly established Royal Society. Here was a man comfortable with the ironies of his time.

Wilkins was tirelessly inquisitive. He posited the possibility of extraterrestrial life on the moon (and designed a flying machine to get there); he speculated on the construction of submarine “arks”; he wrote the first book on cryptography in English; and he fabricated transparent beehives that allowed honey to be extracted without killing the bees inside.

His creation of the irony mark, though, came by way of a project that he intended to be his crowning glory. His “Essay Towards a Real Character and a Philosophical Language” described an artificial language capable of “the distinct expression of all things and notions that fall under discourse”. Just as we sometimes find written language inadequate to express of irony, so Wilkins found it inadequate for everything else besides, and his “real character” was designed to encompass all things and ideas the human mind could conceive of. His irony mark was little more than a footnote to this epic work, a suggestion that ironic statements might be punctuated with an inverted exclamation mark (¡). His was not only the first irony mark; it was also the first to fail.

It took more than a century after Wilkins’s bold but doomed endeavour for the next putative irony mark to appear. And, for now at least, it had migrated across the Channel: if England was not ready to note irony, the Continent most certainly was.

The first of Europe’s steady procession of irony marks appeared in an 1842 issue of a Belgian newspaper named Le Courrier Belge. In an article bemoaning the ceaseless political and martial wrangling of Europe’s “long 19th century”, Jean-Baptiste-Ambroise- Marcellin Jobard, the paper’s proprietor, opened a paragraph with a small mark shaped like a Christmas tree. The foot of his article bore an explanatory note: “ Ceci un point d’ironie.” (Had he lived a century later, Jobard might have appropriated Magritte’s slogan and made it: “ Ceci n’est pas un point d’ironie”.) In a book published the following year, Jobard elaborated on his experiment, explaining that a new family of marks could be created by rotating his Christmas tree to signal irritation, indignation or hesitation.

Jobard, like John Wilkins, was a technologist and inventor: he championed lithography, a novel method of printing; he studied the propagation of sound through hollow pipes; he agitated for the introduction of railways to Belgium; and he lit his home with gas lamps that he had designed.

However, his irony mark was not used beyond his own works. Writing only a decade after Jobard had publicised his creation, Jean-Jacques Rousseau echoed Erasmus by lamenting the apparent lack of punctuation for ironic statements.

The next irony mark was born in fin de siècle France, courtesy of the poet Alcanter de Brahm. In his 1899 essay L’Ostensoir des ironies (“the monstrance of ironies”), de Brahm put forward an irony mark shaped like a stylised, reversed question mark ( ) and spoke of it “taking the form of a whip” to indicate the verbal lashing that irony could inflict. Perhaps more so than his predecessors, de Brahm was aware of the delicate balance to be struck when committing verbal irony to paper – the phrase point d’ironie, he noted, was a pun that also meant “no irony”. As a later scholar remarked of de Brahm’s symbol, can a reader ever be sure that an irony mark is not being used ironically in its own right?

This was of no concern to Hervé Bazin, an acclaimed French novelist and creator of the third and final point d’ironie to appear in print. In 1966 Bazin wrote a light-hearted book on words and language, Plumons l’oiseau, or “Let’s pluck the bird”. Presented as the work of a fictitious professor of linguistics, Plumons l’oiseau was chiefly a plea for spelling reform, though Bazin also devoted a chapter to a set of six proposed “intonation points”. Joining symbols expressing love, conviction, authority, acclamation and doubt was his own point d’ironie, constructed from an exclamation mark crossed by a stroke akin to a single horizontal parenthesis. Bazin explained his mark as follows:

This is an arrangement of the Greek letter ψ. This letter (psi) is an arrow in the bow, corresponding to ps: that is to say, the sound of that same arrow in the air. What could be better to denote irony?

Ultimately, Bazin’s picturesque symbol was no more successful than those of Jobard and de Brahm before it, and it remains the final attempt by a francophone writer to create an irony mark. It was also the last to precede the internet, the arrival of which fostered a new burst of short-lived irony marks. In comparison to the decades that elapsed between those of Jobard, de Brahm and Bazin, digital irony marks (or rather, sarcasm marks, as the internet favours irony’s derisive cousin) seem to crop up every other year. Yet none of these has quite the ironic gravity of their printed predecessors. At the risk of being accused of typographic snobbery, I would contend that the points d’ironie of Jobard, de Brahm and Bazin, cut in steel and cast in lead, have precisely one credible successor – one that, once again, is a European invention.

In 2007, the theme for the Boekenbal, the gala opening of the Dutch national book festival, was “In Praise of Folly – Jest, Irony and Satire” and a new mark of punctuation commissioned for the occasion was launched at the event.

Though conceived primarily as a publicity stunt, the “ironieteken” designed by Bas Jacobs of the European type foundry Underware was a considered addition to the pantheon of existing irony marks. Jacobs conceived his graceful, zigzag ironic exclamation mark (below) to blend in with existing punctuation marks and to be easy to write by hand, and he succeeded admirably on both counts.

Shock note: the mark proposed by Underware

Unfortunately, as one wag pointed out, two ironieteken placed next to each other (to punctuate an especially ironic exclamation, perhaps) bear not a little resemblance to the insignia of the Nazi SS (ϟϟ). Whether because of this or otherwise, the ironieteken remains more a curiosity than a viable punctuation mark.

If irony refuses to be punctuated, perhaps the solution is to mimic an ironic tone of voice. After all, we can already emphasise text in a number of ways, so why not extend our typographic palette to encompass the ironic register? Writing for the Times in February 1982, the columnist Bernard Levin recalled a proposal to do just that: “Much of my time is spent trying to dispel the belief that my words mean the exact opposite of what they say, such an assurance being necessary in view of the apparently unshakeable determination among many readers to misunderstand them.”

“As for trying to be funny – well, long ago Tom Driberg [the Labour MP] proposed that typographers should design a face that would slope in the opposite direction from italics, and be called ‘ironics’.” With jokes set in this typeface, Levin said, no one would have any excuse for failing to see them.

Fittingly, Driberg’s life was a mess of ironies: he was a married, gay High Anglican who lunched with occultists; a leftist politician who revelled in frivolous society gossip; a patriot who spied for both MI5 and the KGB. It seems entirely apt for him to have proposed the creation of a typeface to invest text with a double meaning.

Unfortunately, today’s word-processing software remains steadfastly unable to invest text with Driberg’s ironic tilt, and a sentence terminating in a “¡”, “ ” or ironieteken is more likely to be mistaken for a typographical error than seen as an ironic statement.

Getting irony across in writing remains as simple and as complicated as it ever was. Just say it like you mean it.

Keith Houston is the author of “Shady Characters: Ampersands, Interrobangs and Other Typographical Curiosities” (Particular Books, £16.99)