Illustration by Phil Wrigglesworth

Go look it up. That’s what students who have questions about words are often told. But where should they go? Depending on the question, some resources are better than others, and some aren’t very good at all, no matter what the question. Finding the most helpful word resource for students can be a challenge, especially now that search engines often return millions of results for almost every English word. Here are my picks for the most useful sites arranged by the kinds of questions they try to answer, and for the kinds of questions they may inspire students to ask.

How do I pronounce this word?

Mispronouncing a word can be terribly embarrassing. It’s no wonder that “how do I say this word?” is the third most common use of dictionaries after meaning and spelling.

Any major dictionary site, such as Dictionary.com, Merriam-Webster Online, or my own site, Wordnik, will have both text pronunciations (using proprietary diacritical systems or the International Phonetic Alphabet) and, at least for some words, audio pronunciations. If students have trouble with the written pronunciations, sites should provide keys to explain the symbols. (Because these symbols can be so difficult, Wordnik uses a mouseover technique: roll over the symbols and an explanation pops up.)

Another site, Forvo, offers only pronunciations for words in dozens of languages, including English. Forvo (and Wordnik as well) allows students to record their own pronunciations, once they’ve figured them out, which can be highly motivating.

For a student who’s completely stumped by a pronunciation (especially of a very new or a very old word), there’s a neat search-engine hack: limit your search to books or blogs and use the search “[your word] pronounced.” Remind students to check more than just the top result.

What’s its history?

Etymology can be fascinating, but it’s not an exact science. Students are frequently disappointed to learn that a word’s history is unknown, or that a favorite “just because” story of a word’s origin is merely a good story and not an uncontested fact. If your local library has access to the online Oxford English Dictionary (OED), that’s always the best place to start to find the earliest known use of a word. (Remember that the earliest known use of a word is just that, the first one that has been found, and that since the OED is in the process of a revision that started at the letter M and is now only up to R, words before or after those letters may not have been revised to show newly discovered, earlier uses of a word.)

Google Book Search and Archive.org are two great places to find uses of a word using the search by date functions that might be earlier than those listed in the OED or other dictionaries. Students should be alert for OCR (optical character recognition) errors and possible misdating of sources, which can lead them to the wrong word in the right year or the right word in the wrong year.

Two books about word histories (both from Oxford University Press) might be good additions to a high school library. First there’s Word Myths: Debunking Linguistic Urban Legends (2004) by David Wilton (who also runs the excellent WordOrigins.org website), which debunks the most common untrue-but-entertaining etymologies. Word Origins and How We Know Them: Etymology for Everyone (2005) by Anatoly Liberman explains the process by which etymologies are researched and written, with considerable information on the history of the English language.

What if there’s a word history question that can’t be answered by dictionaries? Check out the American Dialect Society, which has a mailing list where members can help track down the earliest uses of words. If a student’s question is interesting enough, and the student has exhausted other resources, asking a question of the mailing list can be very productive. (However tempting, list members should not be considered to be a homework helpline.)

What does it mean?

“What does it mean?” seems like the most straightforward question a student could have about a word, but meaning is just one aspect of understanding a word and sometimes the least useful. Every teacher has seen students read dictionary definitions and still make complete nonsense when asked to use the word in a sentence.

In fact, “use it in a sentence,” the perennial refrain of teachers attempting to instill vocabulary, is something that should be asked of dictionaries, as well. Since traditional dictionaries, even those online, are based on print works, their entries are often highly compressed and lack any example sentences at all, or they don?t show enough example sentences to help students who need to be able to confidently use the words themselves.

One of the motivations for creating Wordnik was the desire to show as much real context around words as possible since we understand words better in context than we do in isolation, even with the best possible written definition. Wordnik shows as much context as possible for as many words as possible, so even if there’s no traditional dictionary definition, readers should be able to learn about the word naturally, from real examples. Wordnik even shows tweets, so that readers can see the most recent context for any word. (Note: Wordnik is intended to be used by adults, so no content is filtered, and it changes constantly; teachers and librarians should supervise use by younger students.)

I need another word for?

The thesaurus is quite possibly the most abused reference work in any library (or online). Students often run into trouble when they use near-synonyms without taking context into account. Many teachers recommend the subscription-based Visual Thesaurus site because the nonlinear layout puts a hurdle in the way of students who want to pick the longest or fanciest-looking synonym they can find in the shortest amount of time.

Wordnik also offers synonyms, antonyms, and other related words (in the “Related Words” section, which is undergoing a redesign). One interesting feature for students is the “Used in the Same Context” word list. This shows words that are not necessarily synonyms, but which show up in the same kinds of sentences. For instance, for the word “myriad” Wordnik shows “countless * various * multiple * diverse * lesser * numberless” as words that are used in the same contexts as “myriad,” giving a wider picture of the kinds of ways that word can be used.

Students searching for related words should also investigate the “lists” function of Wordnik—”Myriad” appears on 123 lists to date, including a list of words from Greek, a list of units of measurement, and many “beautiful word” and personal word lists.

Now that I know this word, how do I remember it?

Most students will be motivated only to finish their assignments and move on. For those with a more lasting interest, Wordnik allows logged-in users to mark words as “favorites” and to assemble lists (see above) of words for easy reference. (Disorganized students might appreciate being able to make lists of words for assignments right inside the dictionary).

Wordnik word lists are visible to all users, but can be open (anyone can add a word) or closed (only the creator can add a word). Many users keep one list of their words and then make topical lists as their interests develop.

Am I the first person to use this word?

Students love to make up words, and at Wordnik, we like to encourage them. Wordnik shows as much information as we’ve found for any term, even words that have only been used once! (These are often called nonce words.) Students who enjoy making up words can tweet them and see them show up on Wordnik immediately, without being signed in. (The information only becomes permanent if more data becomes available, though.) Signed-in users can leave comments explaining their word and add pronunciations, too.

Older high school students might also enjoy checking to see if their new word has been entered at The Urban Dictionary, although much of the content on that site is not school-appropriate.

Another site for new word information (also intended for adults, but safer than Urban Dictionary) is Paul McFedries’s Word Spy. Word Spy covers new words taken mostly from magazines and newspapers, and provides citations with references.

I'm interested in language: Where can I learn more?

Advanced middle school and high school students with a serious interest in language should check out the “On Language” column of the New York Times (previously written by the late William Safire, and now a biweekly column from The Visual Thesaurus’s Ben Zimmer), and “The Word” column in the Boston Globe, which I write every other week, sharing it with Jan Freeman. Language blogs—mainly intended for adults, but accessible to motivated students—include the landmark Language Log (whose contributors include Mark Liberman and Arnold Zwicky), Literal-Minded (whose author, Neal Whitman, occasionally also writes about language development and children), and Language Hat.

One thing to remember: no word site, however engaging or informative, will help students if language-related tasks are used as punishment. As a favor to students (and dictionary editors) everywhere, please don’t make them look up words, copy them, or create lists of words as a consequence of bad behavior.

Erin McKean is CEO and cofounder of Wordnik and the former editor in chief for American dictionaries at Oxford University Press.