Cracking the Code: Mastering English Words with Multiple Meanings

words with multiple meanings

When a single English word seems to carry multiple meanings, are you ever confused? A word you thought you understood suddenly conveys a completely different meaning.

Is “bow” the gesture of an actor bending at the waist on stage after a performance, or is it the knot of ribbon on a birthday gift? And when you see words like this, are you ever unsure how to pronounce them?

When you’re working on your fluency, you’ll hear multiple meanings quite often in everyday conversation. This can shake your confidence and lead to language anxiety – but it doesn’t have to!

Learning and understanding English words with multiple meanings is possible (and easy).

The best part is that you don’t need a partner for this – you can do it all by yourself.

In this article, I will explain the differences between types of English words with multiple meanings, and provide you with tools to learn them quickly and easily.

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Words that are similar

It is likely that you will come across many words in the English language that look, sound, and mean the same thing, but each has its own unique meaning.


Homonyms are words with identical spelling or pronunciation but entirely different meanings.

Homonyms include both homographs and homophones, which I’ll discuss in detail later.

Even native English speakers may have trouble understanding these types of words.

If you understand the context in which the word is used, you’ll have a much better understanding of its meaning.

Here are a few examples of homonyms:


  • This tree’s bark is brown. (Tree covering.)
  • There is a loud bark coming from that dog. (The sound a dog makes.)

To remember the difference – Imagine a dog barking so loudly that the bark of a tree peels off.


  • (Sporting equipment) I’d like to bring my baseball bat.
  • In that cave, there is a bat. (A nocturnal animal.)

To remember the difference – Imagine walking into a cave and swinging a baseball bat against a rock. Thousands of bats will fly out.


  • I would appreciate it if you did not tear that page out of the textbook. (To rip.)
  • The movie is so sad, I might shed a tear. (Crying tears.)

To remember the difference – It hurt so much that you shed a tear when someone’s tearing up a letter that meant a lot to you.


  • The band played a great song. (A group of musicians.)
  • In order to keep her hair contained, she always wears a hairband.

To remember the differenceHairbands are used to keep the band members’ long, beautiful hair neat and tidy.


  • The date today is January 15th, 2018. (Calendar date.)
  • Let’s go out on a date to eat together for dinner.

To remember the difference – Think about taking your partner out on a date to celebrate your love. The date you choose is February 13.


  • (A type of insect) This fly won’t stop buzzing near my head.
  • Someday, I’d like to fly to Europe. (In an airplane.)

To remember the differenceFlying is what a fly does most of its life.


  • The address of my physical location is 123 Front Street.
  • There is no way we can let this issue go on. (To deal with something.)

To remember the difference – If you receive a letter addressed to someone else, but somehow ends up at your address, you must return it to the sender.


  • (To convey.) I understand what you mean.
  • It’s awfully mean of her, isn’t it? (Unkind.)

To remember the difference – Imagine someone being mean to you when you correct their work because they don’t understand what you mean.


  • It’s a great rock band! (A style of music.)
  • It took the construction crew 60 feet to dig through solid rock (stone).

To remember the difference – Imagine two men digging through hard rock with pickaxes and a radio playing loud rock music next to them.

trainer instructing woman on safety


A homograph is characterized by two or more words that are spelled alike but different in meaning or pronunciation.

Here are several examples:


  • Turn left here, please! (Direction.)
  • I left my purse at home. (Forgot.)

To remember the difference –Imagine you’re at a crossroads and on one side, there’s a big sign pointing to the left. On the other side, you see a person with a puzzled expression, holding a purse and looking back at their house as if they forgot something.


  • What time does your watch say it is? (A time-piece on your wrist.)
  • I’d like to watch my TV show now. (To observe something happen.)

To remember the difference –Picture yourself sitting in front of a TV screen, watching the show. You’re so lost in the show that your eyes become like two big watches.


  • Could you pass the can of beans, please? (A tin of goods.)
  • Can you take me to the store? (Asking for assistance.)

To remember the difference –Imagine asking politely for a can of beans: “Can I please have the can?”


  • Park your car over there. (To stop the vehicle.)
  • We’re going to the park for a picnic. (An outdoor space.)

To remember the difference – Imagine you’re driving to a park with lots of food in your car. You park your car, gather all of the food, and set up a picnic in the park.


  • I saw that car drive by so fast! (To observe.)
  • We’ll need a saw to cut this tree branch. (A tool with blades.)

To remember the difference –Imagine you’re watching two strong men cut down a tree with a steel hand saw. Later, you tell a friend what you saw – two men with a saw.


  • The palms of your hands are dirty. (The underside of a hand.)
  • There are many palm trees along the boardwalk. (Type of tree.)

To remember the difference –Imagine walking along a street lined with palm trees. Each of the palm trees waves in the wind like hands (with palms).


  • The next letter of the alphabet will be “H.” (A character for typing.)
  • I got a letter in the mail today, how exciting! (Note or card.)

To remember the difference –Each letter that you write is composed of individual letters.


  • Alexander IV was the ruler of Egypt from 316–304 B.C. (The King or Queen.)
  • I use a ruler to draw straight lines and measure distances. (A tool that is marked in units to be used as a straight edge or for measuring.)

To remember the difference –Imagine a young king sitting – a ruler – on a throne, wearing a crown and using ruler to measure the length of his royal garments and the size of his kingdom.


  • I love springtime, the flowers are so beautiful. (Season.)
  • He kept his shoes right next to his bed so he could spring into action at a moment’s notice. (Jump.)

To remember the difference –After winter ended, you were so excited for the new season that you kept your shorts and sandals ready so you could spring into spring.


  • Well, it’s hot outside. I suppose we can get ice cream today. (Interjection.)
  • The well has dried up. We can’t get water from there. (A deep hole with fresh water.)

To remember the difference – Imagine digging a well. After finishing, you say to yourself “Well, it’s so hot that I deserve an ice cream.”

woman writing in her notebook


Homophones are words that are pronounced the same as another word but differ in meaning, and are spelled differently.

Here are several examples:

Foul – Fowl

  • The smell of the garbage can is foul. (Unpleasant.)
  • I am looking for waterfowl. Have you seen any ducks or geese? (A type of game bird.)

To remember the difference –imagine a garbage can with a terrible smell rising from it (foul). Inside the can, ducks and geese (fowl) are wearing chef hats, cooking up a gourmet meal.

Groan – Grown

  • All of these meetings are making me groan. (To grumble or be upset.)
  • It’s hard to believe how quickly you’ve grown! (To increase in size.)

To remember the difference –Imagine a group of people sitting in a meeting, collectively groaning due to boredom. Among them, a child is standing tall, showing how much they’ve physically grown.

Holy – Wholly

  • It is the holy month of Ramadan. (Divine.)
  • I wholly disagree with your view on politics. (Entirely.)

To remember the difference –“wholly” is a bigger word than “holy” and means that everything is included.

Mail – Male

  • I need to mail this letter to my aunt. (Use the postal service.)
  • Is the dog a male or female? (Characteristic of boys, men, or the male sex.)

To remember the difference –you must put mail IN a mailbox. The “i” in the word “in” and “mail” can remind you that you put mail IN a mailbox.

I – Eye

  • I am so happy to see you. (Referring to oneself.)
  • Ouch! I hurt my eye. (The organ of sight.)

To remember the difference –Imagine the letter “I” looking at itself in a mirror with two big eyes.

Hour – Our

  • I have one hour left of work today. (Time; 60 minutes.)
  • It’s time to get on our flight to Europe. (Relating to us or ourselves.)

To remember the difference – know that “our” sits within an “hour”.

Meet – Meat

  • Meet me at 3 pm outside the office doors. (To gather.)
  • Steak is a type of meat. (Protein.)

To remember the difference –know that you EAT mEAT.

Weak – Week

  • My legs feel weak after running today. (Lacking strength.)
  • It’s been a week since we last spoke. (7 days.)

To remember the difference –if you run for a week, your legs will feel weak.

Write – Right

  • I will write a letter to the counselor. (To form characters, symbols, etc., on a surface with an instrument such as a pen.)
  • After the next street, turn right. (Direction.)

To remember the difference –know that turning right is the right (correct) direction.

Principal – Principle

  • The principal called me to her office today. (A school director.)
  • It’s the principle that matters! (A fundamental truth.)

To remember the difference –a principal is like a PAL (a friend) to students. PrinciPAL.

woman reading a magazine


A capitonym is a word whose meaning changes according to whether its initial letter is capitalized or not.

They are often homonyms, but not always. They are actually a very specific type of homograph, which, as you remember, are words that are spelled the same but have different meanings and pronunciations.

Here are several capitonyms:


  • Boxing Day is a British holiday, whereas boxing is a sport that involves special gloves and a contained area.


  • Cancer is the fourth sign of the zodiac, whereas cancer is a disease caused by an uncontrollable division of abnormal cells in the body. 


  • The Earth is the planet on which we live, whereas earth refers to the soil we stand on. 


  • March is the third month of the year, whereas military members march in line.


  • May is the fifth month of the year, whereas may expresses possibility or is used when asking permission.


  • Mobile (pronounced moh-beele) is a city in the state of Alabama while being mobile means you can move around freely or easily.


  • The Pentagon is the building that serves as headquarters for the U.S. Department of Defense, whereas a pentagon is a figure with five straight sides and five angles. 


  • Turkey is a country that bridges the continents of Europe and Asia, whereas a turkey is a (mainly) domesticated game bird native to North America.


  • Polish (pronounced poll-ish) refers to someone who is from Poland, whereas polish (pronounced pah-lish) refers to shining the surface of something such as shoes or wooden tables.

How to Understand Words With Multiple Meanings

Understanding words with multiple meanings can be difficult when using traditional language learning methods.

To make multiple meanings stick in your brain, you need variety and context — more than you find in a typical language app or English class!

You need to deeply understand the words in specific contexts.

To help you do that, here are four ways to think and sound like a native English speaker when approaching words that have multiple meanings:

1. Active Discovery

Most English courses spend a lot of time teaching the rules of pronunciation, spelling, and grammar – and there are many exceptions! Despite traditional language learning methods, the best way to learn and remember these rules is through listening and discovery.

I developed an app called Frederick to help anyone teach themselves to read, spell, and pronounce English… instantly! We remember best what we discover through plenty of exposure and interaction.

As you spend time with the app, you’ll discover new words and meanings, including those tricky words with multiple spellings and pronunciations!

two men speaking

2. Recognize the Power of Context

Context is your guiding light when it comes to deeply understanding the intended meaning of a word with multiple meanings.

The words, phrases, and intonation patterns of the speaker can provide hints about the meaning of the word being used.

Which word is being emphasized in the sentence? Is there any body language or gesture happening? Is the speaker asking for information or telling a funny story?

It’s the context that provides these cues so that you have a much greater understanding of what someone is saying.

3. Leverage Naturally Varied Review

Think about how you became fluent in your native language. You listened to many different speakers before you started speaking.

The speakers you listened to used “real” language, not the formal, stiff language you’ve learned in traditional language lessons. Naturally Varied Review harnesses this “real” type of learning – a variety of different native speakers saying similar things.

So when you listen to native English speakers talking about words with multiple meanings, you’ll be exposed to the different contexts in which they are used. You expose yourself to varied content around a particular topic so that you quickly develop a native English vocabulary, and improve your listening.

This gives you a much deeper understanding of the way in which a word with multiple meanings can be used.

4. Fluent For Life

Fluent For Life is my course that GUARANTEES fluency for intermediate to advanced English learners!

If you want to fast-track your fluency and understand words with multiple meanings, you should try Fluent For Life. You’ll get a proven roadmap to English fluency that prepares you for real-life conversations… even if you have no one to practice with!