The Most Annoying Rule of English Grammar That We Put Up With

English, it goes without saying, is a chaotic language. Often described as "three languages in a trench coat," the world's only true lingua franca can sometimes feel like a free-for-all on the grammar front.

Take the following sentence: "Messi is the greatest footballer in Argentina, if not the whole world."

Depending on how you read it, the sentence could either mean "Messi is the greatest footballer in Argentina, but not in the whole world" or "Messi is the greatest footballer in Argentina, and perhaps in the whole world as well."

The fact that the words "if not" can make a sentence be interpreted in two completely different ways must make them a bugbear of legislators, for whom clarity is a virtue.

But I would argue that when it comes to the English language, the worst thing to deal with isn't syntactic ambiguity, but rather a grammar rule that makes writing needlessly complicated.

I'm talking, of course, about the idea of not ending sentences with prepositions.

Though not universally known, this 'rule' is often followed by people who deem themselves authorities on all matters grammatical. When I was at school, I was taught that it was a sin to finish sentences with prepositions. In other words, instead of writing, say, "Who did you go there with?" one really ought to write, "With whom did you go there?"

Or in the case of "That's the tunnel I drove through," we should really be saying, "That's the tunnel through which I drove."

As the rule goes, prepositions such as "at," "with," "in," "from," "by," and "to" shouldn't appear before a full stop, but earlier in the sentence before a pronoun such as "whom" or "which," in order to make sentences appear more "elegant."

But there's just one problem: the rule doesn't actually exist.

Or at least not in the same way that, say, the rules ensuring that "I am" is correct but "he am" isn't, are followed religiously by everyone without a second thought.

That's because the interdiction of sentence-ending prepositions was invented only a few centuries ago, and in dubious circumstances. During the mid-17th century, the English poet John Dryden faulted Ben Jonson for his use of "preposition stranding," writing, "The preposition in the end of the sentence; a common fault with him, and which I have but lately observed in my own writing."

As a lover of Latin, Dryden believed that just as prepositions in Latin always appear before a noun, the ones in English should do likewise. In other words, English should follow in the footsteps of Latin, the latter of which had always been regarded as being more prestigious and sophisticated than the most widely spoken tongue of the British Isles.

His suggestion was just that — a suggestion. And yet, despite its rather inauspicious origins, being nothing more than a personal stylistic preference brought up in a letter, it somehow ended up being adopted by grammarians as a quasi-sacrosanct law.

To be fair, this rule does seem reasonable if you're familiar with languages derived from Latin. In French, the following sentence "C'est le chat dont j'ai parlé" directly translates as "That's the cat of which I spoke."

Yet while English speakers might commonly write, "That's the cat I spoke about," if you were to translate this literally into French as "C'est le chat j'ai parlé de," French speakers would probably give you strange looks. And rightly so: the sentence above is awkward and feels like it's missing a noun after the preposition, not to mention a word between "chat" and "j'ai."

That's because, as a Romance language, French follows the rule about not finishing sentences with prepositions religiously, and so any sentence that violates it must have a good reason to do so, such as in the case of expressions such as "Il faut faire avec."

But here's the thing: English isn't a Romance language, but a Germanic one. What might not sound natural in French can sound perfectly natural in English, and vice versa, simply because, well, they're different languages with different sensibilities.

That's why when Shakespeare writes, "We are such stuff as dreams are made on," the phrase feels more natural than, say, "We are such as stuff as dreams on which are made."

Since English doesn't derive from Latin, it makes little sense to impose Latin-like grammar rules upon it — especially when you consider the fact that the English language's greatest poet was breaking these rules long before they had ever been prescribed.

But since so many grammarians take the infamous preposition rule to be self-evident, possibly wallowing in the sense of superiority that their supposed knowledge of it affords them, anyone writing in English who is aware of its dubiousness is thrust into an impossible dilemma.

If you were to ignore the preposition rule and write something like, "This is the greatest playing surface to play on," the powers that be might lord it over you for apparently not knowing the rules of grammar. And, as we all know, there's nothing more annoying than someone who knows less than you believing themselves to know more.

But if you were to write "This is the greatest playing surface on which to play," even though the sentence might sound learned, it just can't help but appear pompous and unnatural.

In other words, you have to choose between sounding ignorant or pretentious; there's no middle ground.

The obvious solution, then, would be to rephrase the sentence entirely and write something like "This is the greatest playing surface for sports players." Yet it strikes me as pretty unreasonable, if not ludicrous, that we're forced to tiptoe around certain sentence structures as a way of appeasing grammar gatekeepers, while simultaneously making pains not to sound stiff and awkward.

Then there's the matter of phrasal verbs that have a way of compounding matters. A notable feature of Germanic languages, phrasal verbs are multi-word verbs composed of a verb and a particle that tend to have idiomatic meanings different from the literal meanings of the individual words themselves. In English, phrasal verbs like "get up," "get down," get in," "get out," "get over," "get on," "get by," and "get through" may all begin with the verb 'get', but in each case the prepositions following the 'get' ensure they have nothing in common with each other.

Native speakers of English are used to phrasal verbs, but their ease with using them may have to do partly with the fact that the words are always yoked together.

So what happens when phrasal verbs come into contact with the preposition rule? You get ridiculous sentences like "This is the sort of English up with which I will not put."

Often attributed to Winston Churchill, it makes abundantly clear where he stands on the preposition rule issue, showing just how tortured English can sound if the rule were followed to the letter.

So just like how rules forbidding writing sentence fragments, splitting infinitives and beginning sentences with conjunctions like "with" and "so" and "and" or "or" are artificial constraints that shouldn't be taken seriously, in an ideal world, we should be able to dispense with the preposition rule entirely without raising eyebrows.

Because to slavishly follow groundless grammar rules is such a pain to put up with.