You Are Entitled to No More Indecent Prepositions

You know how to capitalize in title case (also known as headline style), right? Let’s have a little fun. Which of these titles are capitalized correctly according to The Chicago Manual of Style? 

1. Here’s to a World Where Style is Easy 

2. To Turn On the TV, Press on the On Button 

3. Running out the Door and Then Back In for Lunch 

4. Some Concerning Rules concerning Capitalization 

5. A Disquisition regarding a Book wanting a Cover 

6. The Case For and Against AI 

So which ones are right? Well… it depends, as we will see. 

The “Proper” Rules

Many people, of course, don’t know the “proper” rules and will just capitalize every word: 

Here’s To A World Where Style Is Easy 

Since you’re the kind of person who reads an article about capitalization, you undoubtedly know that this is not the way your school teachers wanted, and not the way The Chicago Manual of Style wants, either. And many people do know this, but just have a sense that they shouldn’t capitalize the little unstressed words: 

Here’s to a World Where Style is Easy 

Ah, so close! But is is a verb, and so it needs to be capitalized (so quiz sentence 1 is wrong!). 

The basic rule in Chicago style is that you capitalize the first word, capitalize the last word, and capitalize all the other words except articles (a, an, the), common coordinating conjunctions (and, but, for, or, nor), and, with exceptions, prepositions. There are a few additional details: don’t capitalize to or as even when they’re not used as prepositions, don’t capitalize parts of proper names that aren’t normally capitalized (e.g., de, von), don’t capitalize the parts of scientific names that aren’t normally capitalized (e.g., the c in E. coli) … not to mention dark rumblings, hushed mumblings and common confusion and consternation about which prepositions can be capitalized. 

Up to (and including) the 17th edition of The Chicago Manual of Style, the rule has been “lowercase prepositions, regardless of length, except when they are used adverbially or adjectivally.” Adverbially or adjectivally, they explain, means things such as “up in Look Up, down in Turn Down, on in The On Button, to in Come To, etc.” (so quiz sentences 2 and 3 are correct!). They give examples to illustrate this, including 

Sitting on the Floor in an Empty Room 
but 
Turn On, Tune In, and Enjoy 

and 

Four Theories concerning the Gospel according to Matthew 

But, um, that concerning is… concerning. And according to is a rather indecent preposition – indecently long, at least. 

Here’s the deal: according to this rule, when concerning is used prepositionally, you lowercase it. Otherwise, you capitalize it. What this means is that you could get something like this: 

Some Concerning Rules concerning Capitalization Are Concerning Editors 

…because the first concerning is an adjective, the third one is a participle of a verb, but the second is a preposition. 

Oh, come on! (Which, by the way, would be capitalized “Oh, Come On!” because the on is used adverbially in the phrasal verb.) 

Prepositions, or not? 

What this means is not just that you sometimes have concerningly long words lowercased in titles, but also that you have to remember (and expect your readers to understand) that quite a lot of words that they may not think of as prepositions are, at least sometimes – including: 

• aboard 

• above 

• against 

• alongside 

• apropos 

• astride 

• barring 

• beneath 

• between 

• beyond 

• excepting 

• following 

• including 

• notwithstanding 

• pending 

• regarding 

• respecting 

• throughout 

• towards 

• underneath 

• wanting 

Yes, that’s right – the rule says you should do this: 

A Disquisition regarding a Book wanting a Cover notwithstanding Its Brevity 

For many of us, this has been a rule that is, to quote Hamlet, “more honored in the breach than the observance” – in both senses: most people don’t follow it, and that’s for the best. But rules are rules, you know! 

Here Comes the Revolution

Well, guess what: in the revolutionary, shocking, earth-shattering, mind-blowingly liberal 18th edition of Chicago, they have changed exactly one thing in the capitalization rules, and it is causing much rejoicing in the land: they changed “lowercase prepositions, regardless of length, except when they are used adverbially or adjectivally” to “lowercase prepositions of fewer than five letters, except when they are used adverbially or adjectivally.” 

You see that? Of fewer than five letters! This means not only has their example sentence changed to “Four Theories Concerning the Gospel According to Matthew,” but they’ve added the example sentence “Writing Under a Deadline and Without an Editor” (they could also add “Writing on a Deadline with an Editor,” but they didn’t). And it means quiz sentences 4 and 5 have gone from right to wrong! 

They also added a further exception and insight: 

In rare cases, a shorter preposition may be capitalized when paired with a longer preposition (for in For and Against). Note that the five-letter rule includes abbreviations (e.g., Versus would be capitalized, but vs. would not be). 

They give the example “The Case For and Against AI”. That may make you say “Hey! Upper-case For!” but consider the alternative – “The Case for and Against AI” – or the old rule: “The Case for and against AI.” So, quiz sentence 6 is correct after all. 

Of course, applying these rules still requires knowing them and paying attention – and having the wisdom to know when rewriting something might be better. But if you’re an editor, that’s how you earn your money! 

A Helping Hand

The good news is that there is also some help. If you’re using PerfectIt and you have an subscription to The Chicago Manual of Style Online, you can use the Chicago style checker. It won’t simply fix everything for you, but it will flag possible issues and remind you of the latest version of the rule!

If you haven’t tried PerfectIt yet, there’s a free trial. Capitalize on it!