‘Rules are made to be broken.’ Whoever said that clearly wasn’t a cricket fan. Or, you might think, a copywriter. But there are some rules of grammar that, while widely accepted and obeyed, can and even should be flouted when the occasion demands.

Split infinitives

‘To boldly go where no man has gone before.’ Strictly speaking, it should have been ‘to go boldly’, or ‘boldly to go’. But, as Gene Roddenberry well knew, either of those would have sounded ludicrous. If you want to really make an impact, there are times when it’s practically essential to boldly split infinitives no one has split before.

Prepositions (ending sentences with)

Without rules, our society would surely descend into chaos

‘Never use a preposition to end a sentence with.’ To comply with itself, this gem should read ‘with which to end a sentence’. But if you always did that, your copywriting would end up sounding like Brideshead Revisited.

Prepositions and conjunctions (beginning sentences with)

You shouldn’t really begin sentences with prepositions (‘with’, ‘of’, ‘for’ etc) or with conjunctions (‘but’, ‘and’, ‘or’, ‘so’, etc). But there are times when it’s essential. And desirable, to add punch and rhythm to your copywriting. So relax about this one too. 

Sentence without verbs

A sentence should always have a ‘doing’ word, or verb. But there are many sharp, conversational utterances that lack them, and if you want that tone in your copywriting, you’ll need to emulate them. Like this.

Missing out ‘that’

‘Everybody knows you can’t just miss out words’. No, everybody knows that you can’t just miss out words. But you can, as long as the meaning remains crystal clear to the reader. And shorter is nearly always better.

And here’s a few you can’t break: that and which, possessive apostrophes, decades (‘80s’, not ‘80’s’), its/it’s and their/there/they’re. If you don’t know what I’m on about, get yourself a copywriter!

I used to have a big problem with the choice between ‘that’ and ‘which’. Looking at many articles and advertisements, it seems I’m not alone – many writers and professionals regularly get this one wrong. A common problem seems to be overusing ‘which’ in place of ‘that’, perhaps because it seems more classy and formal. Or perhaps people think there’s no difference, and it’s just a matter of preference. Unfortunately, it’s not – one or other is always right, and they are never interchangeable.

Some years ago, an assistant editor (who I was supposed to be training) helped me out with ‘that defines, which describes’. This concisely sums up the difference: ‘that’ introduces an essential definition of the subject, while ‘which’ introduces an optional description of it. The following two sentences illustrate this nicely:

He stopped the first car that was driven by a woman.
He stopped the first car, which was driven by a woman.

In the first sentence, ‘that’ introduces an essential definition. Without the rest of the sentence, the meaning is completely different. But in the second, ‘which’ introduces a description, without which the sentence would still have the same meaning.

Note also that ‘which’ always follows a comma, while ‘that’ runs straight on. The comma denotes a pause in speech, as you can confirm by reading out the two examples above. So you can always say your sentence out loud, see if a pause is needed, and make your selection on that basis. (If you pause, there’s a comma and therefore it’s ‘which’.)

Finally, if you use Microsoft Word (doesn’t everyone?) you can simply turn on its live grammar check feature and it will highlight your that/which howlers (with green wavy underlining). I’ve just tried it on the examples above and it worked – in fact, this is one of the few areas where it’s reliable pretty much all of the time. But it can get confused with longer, more complex sentences, so it pays to know the rule yourself.