English has an unusual number of words that sound identical and mean entirely different things. They're the errors that survive spellcheck, because both spellings are real words — the software has no way to know which one you meant.
Why English has so many
Two reasons, both historical. First, English borrowed from Germanic, French, Latin and Greek, and words from different sources drifted into the same pronunciation while keeping their original spellings. Meat is Old English, meet is Old English too — but they were distinct sounds until the Great Vowel Shift merged them.
Second, the sounds kept simplifying while spelling stood still. Knight and night were once clearly different; the k and the throaty gh were both pronounced. When they fell silent, two different words became one sound.
The ones that matter most
| Words | How to keep them apart |
|---|---|
| their / there / they're | their = belonging to them · there = a place (contains here) · they're = they are |
| your / you're | you're = you are, always. If "you are" fits, use the apostrophe |
| its / it's | it's = it is. The possessive has no apostrophe, unlike every other possessive — which is why this one catches everyone |
| affect / effect | affect is usually the verb, effect usually the noun. It affects you; it has an effect |
| then / than | then = time · than = comparison |
| lose / loose | lose a game · trousers are loose |
| advice / advise | Not homophones, but constantly confused: the noun ends in a hiss, the verb in a buzz |
| principal / principle | The principal is your pal, or the main thing · a principle is a rule |
| complement / compliment | complement completes · a compliment is praise |
| stationary / stationery | stationary = not moving · stationery = envelopes |
The ones that just have to be met
Bare and bear. Break and brake. Flour and flower. Peace and piece. Right, write, rite and wright. To, too and two. No mnemonic covers these; you meet them and eventually they separate.
The technique that works
Don't memorise the pair. Memorise one sentence per word, and make the sentence do the disambiguating: "They're over there with their coats." A single sentence holding all three fixes them better than three separate definitions, because the contrast is the thing you're actually learning.
Save the sentence, not the pair. More on why context beats definitions here.