Its/It's, Their/There, Your/You're, Then/Than

Some words sound exactly the same but mean completely different things — and that's precisely why they're so easy to get wrong. When you read a sentence back in your head, your and you're sound identical, so your eye glides straight over the wrong one without stopping. Your ear simply can't help you here. The fix isn't to listen harder; it's to have a quick test for each pair that settles it in a second. Here are the ones that get circled most, with a trick for each — and one big habit that catches nearly all of them.

Why these are so easy to slip on

Before the tests, it helps to know why these trip everyone up, because then you'll stop feeling silly about it. When you write, your hand often auto-completes the little words from sound while your brain is busy with the actual meaning of the sentence. So its and it's come out almost at random, because they sound the same and both look like real words. And they are both real words — which means spellcheck won't save you either. The software can tell you if a word is misspelt, but it can't read your mind about which meaning you wanted. That decision stays yours, and it's why a deliberate check matters.

its / it's

its = belonging to it (no apostrophe).

The dog wagged its tail. → "the dog wagged it is tail" is nonsense, so no apostrophe.

it's = it is (or it has). If you can stretch it to it is, use the apostrophe.

It's raining. → It is raining. ✓

This is the one that gets marked most, and it feels unfair, because normally an apostrophe shows belonging — the cat's paw. But its is a special case, like his and hers, which don't take an apostrophe either. Don't fight it; just run the it is test and the quirk turns into a tool.

your / you're

your = belonging to you.

Is this your coat? → "Is this you are coat" is nonsense, so it's your.

you're = you are. Stretch it out to test.

You're late. → You are late. ✓

Same machinery as its/it's, exactly. Swap in you are and keep whichever version still makes sense.

then / than

• then = time (next, after that): We ate, then we left.

than = comparing: taller than me, better than ever.

Trick: compare → than (both have an a).

There's almost always a giveaway word sitting near than: more, less, better, worse, taller, bigger, rather. If you spot one of those, you're comparing, so you want than with an a. If you're really talking about time — what happened next — it's then.

their / there / they're

All three sound like thair, which is why they pile up so often:

• their = belonging (whose? theirs): their bags, their game.
• there = a place (like here): over there, there's a spider. Memory hook: there has here hidden inside it — both are about place.
• they're = they are: they're late → they are late. ✓

The one big fix

Whenever an apostrophe word turns up (it's, you're, they're), try stretching it back to two words (it is, you are, they are). If that works, keep the apostrophe. If not, use the "belonging" spelling. That single habit clears up most of these traps at once — you don't need a different trick for every word, just the one stretch test plus the here-in-there hook for the place word.

Watch one sentence carry three traps

Here's the kind of line that turns up in a rushed message, wrong three times over:

"Your going to love there new game more then the last one."

• Your → you are going to love → works → You're.
• there → whose game is it? → it belongs to them → their.
• then → there's more sitting right beside it → comparing → than.

Fixed: "You're going to love their new game more than the last one." Same sentence, and now it doesn't wince. See how the tests do all the work — no guessing.

Do a special sweep — normal reading skips these

Here's the trap inside the trap. When you proofread normally, you read for meaning — and your brain fills in the right word even when the wrong one is printed, because it knows what you meant. So your ordinary read-through sails straight past these every time. The answer is a second, targeted pass. When you've finished something that matters, spend thirty seconds hunting only for these pairs — its/it's, your/you're, their/there/they're, then/than — and run the test on each one you land on. Don't re-read for sense; let your eye bounce along looking just for those shapes. It's the highest-value half-minute in the whole edit.

Why it matters

You might think, if the meaning is clear, does it really matter? In a text to a friend, honestly, no one cares. But in schoolwork, an exam, or a job application, these little slips are the first thing a marker's eye snags on — and because they're so well known, getting them wrong reads as carelessness even when your ideas are excellent. The flip side is the good news: because the tests are so quick and reliable, this is one of the easiest ways to make your writing look sharp. A single sweep and you've fixed the errors that people notice most.

Quick check

Choose the right one:

1. (Its / It's) too cold for (its / it's) usual walk.

2. (Your / You're) going to love (your / you're) present.

3. Bigger (then / than) ever.

4. (There / Their / They're) going to leave (there / their / they're) bags over (there / their / they're).

5. We finished early, (then / than) we went home.

6. The robot closed (its / it's) hatch.

Where next

• Their, There or They're? — the classic three-way trap, in full.
• Apostrophes: The Two Jobs — where it's and you're come from.
• Meaning-Pairs: Affect/Effect, Accept/Except — words that look alike but differ in meaning.