Your Copy Sucks: That vs. Which vs. Wait, what?

close-up of cloth pouch with scrabble tilesJust admit it. ADMIT IT. You don’t know when to use “that” and when to use “which” in a sentence.

Don’t cry! Nobody does. Seriously, no one can remember the rules for that/which because they are so. Freakin’. Difficult to remember when you’re in the middle of writing. But some of you actually care about your writing, and for you, I will break it down. The rest of you can go, I don’t know, eat cheez doodles and watch the local news.

Here’s what the Chicago Manual of Style (praise be His name) has to say about that/which:

that; which. These are both relative pronouns (see 5.58–62). In polished American prose, that is used restrictively to narrow a category or identify a particular item being talked about {any building that is taller must be outside the state}; which is used nonrestrictively—not to narrow a class or identify a particular item but to add something about an item already identified {alongside the officer trotted a toy poodle, which is hardly a typical type of police dog}. Which should be used restrictively only when it is proceeded by a preposition {the situation in which we find ourselves}. Otherwise it is almost always preceded by a comma, a parenthesis, or a dash. In British English, writers and editors seldom observe the distinction between the two words.

Another bloody reason we should have all just kept our mouths shut in 1776. (J/K. USA, USA! Did you SEE us win that men’s gold in ice skating? Okay, back to grammar.)

Listen, if any of you read that piece of information from Chicago and actually understood it, then I defer to you, Professor Nash. The rest of us will continue wallowing in the filth of our confusion. To put it another way: what the f#@% does that mean!?

Calm yourself, child! Mama will sort it all out for you.

The easiest thing I can tell you is this: That is used when you need a phrase to make the sentence say what you need it to say. Which is used to introduce a phrase that isn’t actually necessary in order for the sentence to make sense. That’s what Chicago means when it talks about restrictive and nonrestrictive use.

Let’s try some examples.

This is the drink that she bought me.

Can you imagine taking out everything in that sentence after that? You would just be saying “this is the drink” and that certainly doesn’t make much sense, does it? It doesn’t answer the question of the person who asked you, “Hey, what’s that thing in your hands with the ice cubes and the liquid?”

Compare that to:

This is a scotch and soda, which is a refreshing combination of single-malt and carbonated water.

See? If you take out everything after which, you still have a perfectly respectable sentence. The phrase beginning with which just gives you some extra information, observation, or illumination.

But wait! The scandalous lady that is American English throws you yet another curveball. Sometimes which can be used restrictively, in a way that makes it and its phrase necessary for the sentence to make sense. I know. It’s a dirty trick. But you can easily figure out when it’s kosher if you follow the age-old rule (which I flaunt when it suits me) that states Thou Shalt Never End a Sentence with a Preposition.


That’s the knife that he stabbed the bear with.

is incorrect, while

That’s the knife with which he stabbed the bear.

is totally cool. Unless you like bears.

See how the preposition “with” was moved from the end of the phrase to the middle? That preposition makes it okie dokie to use which in a necessary, un-throw-away-able phrase.

Of course, if you hate all these rules, you can become a British citizen. But then you would have lost two wars to America, and honestly, are you going to let your grammar anxiety do that to you? Go conquer that which you fear.

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  • bethvonbehren

    Here's another easy way to remember it. If you can put your clause into parentheses, and it still works, then you know it should be a “which” clause. Also, ALWAYS put a comma in front of a “which” clause. Yep, the Brits don't do that, but we know their language better than they do, right?

    Btw, “This is the drink that she bought me” is a really bad example. You probably wouldn't even use “that” here. I would write this sentence: “This is the drink she bought me” or “This is the drink she brought for me.” I wouldn't use “that” here, which brings up another point. [And there's a good use of a “which” clause.] Most people use “that” waaaay too often. One proofreading rule I like to use before I go to print on anything: Go back through it one more time and see if you can take out any “that”s. Your prose will love you for it.

  • 1. Yes, always put a comma in front of a “which” clause unless it's restrictive.

    2. My examples suck. Wa wa waaaaaamp.

  • stephmajercik

    I had to laugh when I read this because when I first started learning German grammar, I would become frustrated and lost in all the rules and exceptions and I would always ask my teacher “Why can't this be more like English? English is so easy!” And then she would fire back at me with an example of how English is not easy.

    I think this post clarified this problem really well!

  • Doug

    As Churchill famously (probably an apocryphal attribution) said: “Ending a sentence with a preposition is something up with which I will not put.”

  • jgrubb

    I am much more bothered by the ubiquitous use of “that” when “who” is correct.

    “She is the person WHO asked for clarification.”

    Everyone seems to be using “that” instead.

  • My schoolteacher always told us that people were not “witches” or “thats.” But it gets hazy when you're referring to a person by their title or their thing-ness, because then they don't sound like a person.

  • Ahh, Churchill. My favorite cigar-smoking nudist.

    Another apocryphal saying from him, upon being told that a military officer had been caught having sexual relations with another male solider in St. James' park one night:

    “Wasn't it rather cold last night?”

    “Uh, yes sir, it was one of the coldest on record.”

    “Hm. Makes you proud to be British.”

  • Every language is funky in some ways, except for Esperanto which has no irregular verbs or plurals or anything. But no one speaks Esperanto; it's a silly thing.

  • Larry Schaffel

    First I want to protest Ms. Diederich's observation than none of us can distinguish that from which. I almost make a living making that distintion in copy that I edit. I confess I can't remember the technical explanation, but who can forget the example in the little grammar bible, Strunk's Elements of Style, that shows how “The books that belong to me are on your desk” distinguishes those few books from “The books, which belong to me, are on your desk” that identifies all the books on the desk? I believe Strunk always puts a comma before which as another landmark,

  • Derek

    In the example about bears, could you take “that” out completley and go with, “That’s the knife he stabbed the bear with,”?

  • KK

    >>But you can easily figure out when it’s kosher if you follow the age-old rule (which I flaunt when it suits me) that states Thou Shalt Never End a Sentence with a Preposition.

    Perhaps your next topic could be “flaunt” vs. “flout.”

  • Aw man, we could start an internet fight, but I went with the 4th definition here:

    But hey, if you don't agree, then it's a pretty funny pun, huh? 😀

  • Sure, if you want bears to win.

  • Dude, high five for you! I would have pulled out the Strunk & White, but Chicago doesn't follow the comma rule. Not sure about AP; guessing no? This is where it gets confusing!

    I guess the point is, since there are so many different American style guides, consistency is the best guide.

  • alangraner

    This is the best explanation I've ever read.

  • Nixxie

    Great article. Well written. I should have no more issues with that and which. Thanks!

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