One of the things I learned in my 10 years of teaching grammar to undergraduates is that “it” is torture.

• For anyone paying attention that “it” is a lovely little nightmare known as an unclear pronoun reference. Am I saying that teaching grammar is torture or that learning grammar is torture? I left it confusing for effect, and because on any given day, it’s up for grabs.

While, it is true that occasionally  teaching is not fun, what I am referring to with that pronoun is learning grammar. Learning grammar, especially if you are doing it when you are older than middle school, is largely misery. And one of the primary sources for that misery is the ever-changing and oft loosely applied rules for certain elements of a sentence. One such monster? The relative pronoun.

• If you don’t know what a relative pronoun is, stop here and go study the section on the main Tongue Untied Web site.

Okay. Back to the point: Relative pronouns offer people struggling with grammar a special little brand of torture. At the top of the misery pyramid is trying to determine whether to use “who” or “whom,” but a close second is the confusion between “which” and “that.” Now, The Tongue Untied is willing to acknowledge that for, oh let’s say a half a millennium, people have used the two interchangeably, but we are not willing to admit that they are right.

We have rules here, and the one governing the use of “which” and “that” is as follows: Use “that” for introducing restrictive clauses and “which” for introducing non-restrictive clauses.

ARGH! Another grammar term. If you don’t know what a clause is, learn it here, but for the sake of moving this along, here’s a short primer. A clause has a subject and a verb.

The clauses using relative pronouns (i.e. who, whom, that, which) are dependent clauses. They need another clauses (usually an independent clause) to function. And the relative pronoun in the dependent clause is referring to a noun in the independent clause.

• The man whom they arrested was innocent. “whom” relates to (see how we get “relative”?) the “man.”

Okay. When the information in that dependent clause is essential (restrictive) to the meaning of the sentence (and we are not talking about people) then we use “that.”

• The hot dog that Ethan ate was spoiled. (we need that next clause to know just exactly what hot dog we are talking about.)

When the information in the dependent clause is not essential (non-restrictive) to the meaning of the sentence (and we are not talking about people), then we use “which.”

• Your new haircut, which is the best one you have had in years, makes you look like a movie star.

Learn the rule and you have averted yet another grammar disaster. Fail to and you have missed an opportunity to feel superior.

Perhaps no piece of punctuation gives us more trouble than the hyphen, in particular when we are trying to decide whether to hyphenate a compound modifier. In that realm, the average writer is as consistent as the stock market these days.

So, let’s review:

When a noun has more than one modifier, the modifiers are hyphenated when they act as a unit. In other words, they refer to the noun in a collective way. For example, we would refer to an “almost-empty bottle,” or a “soft-peddling approach.” Or an “orange-yellow sky.”

The rule is that you use a hyphen when the individual elements of the modifier cannot work alone without changing the meaning of the phrase. So, in the previous example, you wouldn’t say “almost bottle,” nor is the meaning “empty bottle.” Same thing with “soft approach.” Of course, you could say “orange sky,” but that is not the intended meaning.

Simple, right? Well, yes and no. The problem is the rule is clear for only very specific set of circumstances.  It is the complications and exceptions to the rule that not only cause the problems but also explain why writers muck it up so often.

First of all, we need to distinguish compound modifiers from a simple series of modifiers. For example, we wouldn’t hyphenate “cold, dark night.” The individual modifiers work just fine alone. “A cold night.” “A dark night.”

And we also need to watch out for modifiers that are working to enhance everything in the phrase that follows them. For example, “hazy blue sky.” In this case “hazy” is modifying “blue sky,” rather than acting as a compound with “blue” to modify “sky.” It is worth noting, I suppose, that if you were waxing poetic and describing a shade of blue called “hazy blue,” you would consider hyphenating it.

The point of using a hyphen is to signal the reader to consider the two words together before moving on. We, as readers, are trained to think of modifiers as stand alone entities and writers need to do their part to interrupt that training when the sentence requires it.

Along the same lines: Remember that, in most styles, compound modifiers that include an “ly” adverb are not hyphenated. Why? Because readers expect “ly” adverbs to work with another modifier to do their jobs. So, we would not write “widely-distributed information.” But we would write “wide-mouthed frog.”

And just to add a couple more things to the mix.

1. We do not use hyphens with compound modifiers that routinely appear together. For example, we do not hyphenate “High School” in “High School Musical.” Or “men’s basketball” in “men’s basketball team.”
2. We do not hyphenate adjectives that have been made comparative or superlative by “most” and “more” The correct usage is “most talented writer” and “more qualified applicant.”

Well, that is probably as clear as mud, but you have to start somewhere. Good Luck