If I told you my co-worker coauthored a semi-inspirational and semicoherent work about a nonviolent and non-meat-eating anti-inflammatory antihero midcentury in the mid-20th-century, would you march on Washington, unfunded and un-unionized, to demand our leaders simplify hyphenation rules for prefixes?

What if I told you that, according to the “Chicago Manual of Style,” every one of the seemingly nonsensical hyphenation choices above is correct? Then would you be ultraoutraged and ultra-angry?

We've covered hyphenation here before. And I don't want to re-cover a topic from which you may not recover. Instead I'll aim for a type of re-creation that doubles as recreation as we look at one very specific area of hyphenation: that is, how to use them with prefixes.

Here's the short answer: Nobody knows. Hyphenation of prefixes is an extremely messy business. Ditto that for suffixes. That's why anyone who's ever felt inadequate because he didn't know whether to write “pre-empt” or “preempt” was really just the victim of a chaotic system of semicoherent and semi-intellectual semiguidelines.

So what should you do? First, don't feel bad about your hyphenation skills. The rules are ridiculously complicated. They're also disputed. In many instances, style guides and reference books disagree. And while one source might say it's “pre-empt,” as does “Webster's New World College Dictionary,” another would insist it's “preempt,” as does “Merriam-Webster” Online.

Second, know that common compounds are often in the dictionary, as we saw with “preempt” and “pre-empt” above.

Third, for less-common combinations, know that there are some basic guidelines that can help you.

Fourth, know that within these guidelines are plenty of exceptions that often allow your common sense to prevail.

The “Associated Press Stylebook,” which many newspapers follow, and the “Chicago Manual of Style,” which most book editors follow, agree on the basics. They say, in general, don't hyphenate prefixes. They also agree on many of the exceptions.

One exception occurs, they say, when a prefix comes before a proper noun or any capitalized word. In those cases, use a hyphen. Think anti-French and pro-Canadian in the pre-Tudor post-Roman age. Associated Press and Chicago agree on that.

Often, when a prefix ends with a vowel and the word that follows starts with the same vowel, a hyphen is needed, style guides agree. That's why you can be megasmart and mega-altruistic. But the two style guides explain it differently. Associated Press says the rule applies to all vowels, though mentions some words are exceptions: notably “cooperate” and “coordinate.” Chicago says that the rule applies only to prefixes ending in A or I. Therefore, a strict interpretation of Chicago Manual rules would allow you to write “protooptimal” even though Associated Press would demand you write “proto-optimal.”

Associated Press and the Chicago Manual also agree that doubled prefixes take hyphens. Associated Press' example is “sub-subparagraph.” Chicago's eerily similar yet slightly snootier example is “sub-subentry.”

There are plenty of exceptions, but style guides disagree on what those exceptions are. Chicago tells us we can hyphenate whenever a combination of letters or syllables “might cause a misreading.” Their examples include “pro-life.” Seems to me they could do a better job of explaining why “prolife” would be any more likely to cause a misreading than “promarket,” which they say has no hyphen. But that just goes to show you that your own judgment is also an excellent resource. If a rule “seems wrong,” there are probably lots of experts that would agree with you.

Perhaps the best one to commit to memory: Both style guides prefer “co-worker” to “coworker.”

But in general, when you need to be 100% “right,” all you can do is check your style guide. The rest of the time, just rely on these simple guidelines combined with your own ever-ready and everlasting good judgment.

?JUNE CASAGRANDE is a freelance writer and author of “Grammar Snobs Are Great Big Meanies” and “Mortal Syntax: 101 Language Choices That Will Get You Clobbered by the Grammar Snobs — Even If You're Right.” She may be reached at JuneTCN@aol.com.

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