Just 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:

5.202
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.

Therefore,

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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