15 Difficult English Words and Phrases That Have Opposite Meanings

Can you feel a color?

You actually can, but probably not in the way you’re thinking.

We’ll make it clear with an example:

In English, you can say something is the color “blue,” or you could use a more exact synonym like “indigo” or “teal.”

You might also feel “sad,” but you could say you’re feeling “down in the dumps” or “depressed.” To express a low feeling, you can also say you’re “feeling blue.”

Did you see that? “Blue” is both a color and a feeling!

Many English words have more than one meaning, just like “blue.”

Sometimes, however, a word changes so much over time that it ends up with two meanings that are complete opposites.

This doesn’t happen very often, but it does happen. And when it does, you need to know both meanings to understand which one is being used.

The 15 English words and phrases below are surprisingly common, but each has two very different definitions. Come see if you know both meanings!

Why Is English Sometimes Confusing?

The English language is made up of many other languages. There are words with Latin and Greek origins, words “borrowed” from other languages like French, and many other constantly changing parts.

Throughout the years, the language has grown. Some words changed meanings, while others completely disappeared. If you go back just a little while, you will find a different language.

So it’s no surprise that today, the English language can be confusing!

And thanks to the Internet, the English language is changing faster than ever, with new words being added constantly. The word “literally,” for example, is often used incorrectly, as we explained here. So many people use the word incorrectly, though, that the “wrong” meaning has become accepted. Some dictionaries are even starting to include the incorrect meaning as a valid (correct) one.

As you learn English, don’t forget that words and meanings are always changing. It might sometimes make learning more difficult, but it also makes it so much more interesting!

Why Opposite Meanings Exist in the English Language

English is full of contradictions: ideas that are opposed to one another. Some are silly, while others are frustrating to learn. For example, why do we drive in a parkway but park in a driveway?

If you look at the history of the words “drive” and “park,” you learn that these words have simply changed over the years. (Parkways existed before cars for a different purpose, and driveways used to be much longer strips of road.) But they’re still confusing and contradictory!

Sometimes, words contradict themselves so much that they become their own opposites. Words that have opposing meanings are sometimes called “contronyms” or “auto-antonyms,” and they can be used to mean opposite things.

Why does this happen? There are many reasons a word might evolve two very different meanings, but three possibilities are:

  • The word comes from two different origin words. Sometimes words get two different meanings because they were originally two different words! The word “bound,” for example, comes from a number of words in Germanic and French, like the Germanic buan (to dwell, or to live) and the Old English bindan (to tie up).
  • The word uses multiple meanings of its origin word. For example, the word “to leave” comes from the Old English word lǣfan, which means “to give to someone,” but also “to remain in place.”
  • The word is so commonly misused that its meaning was changed. Words like “literally” and “nonplussed” (#1 and #2 below) changed their meaning because of frequent misuse.

The best way to remember opposing words is to start using them right away. The fact that they’re silly and seem backwards will actually make them easier to remember. Our brains remember things better when there’s something odd about them.

You can tell which meaning is being used through context. Context involves the other words in the sentence, and even the way a sentence is spoken. For example, if your friend tells you she is “literally rolling on the floor laughing,” you can figure out she’s using “literally” as an exaggeration. (Unless she is actually rolling around on the floor laughing, in which case she is using “literally” to mean “actually and without exaggeration.”)

The list below has English words and phrases that have opposite meanings. Make sure you know them both!

15 Difficult English Words and Phrases That Have Opposite Meanings

1. Literally

Originally, this word meant something that was exact, and was the opposite of “figuratively.” Today, through much misuse, the word is most often used to exaggerate something, and make it seem bigger and more important.

Meaning #1: Exact and not exaggerated.

There were literally thousands of butterflies flying all around us.

Note: This means that if someone had counted all of the butterflies, there would have actually been thousands.

Meaning #2: Exaggerated for emphasis, and not necessarily true.

That is literally the ugliest bag in the world.

Note: There are likely other bags that are uglier than this bag, so it’s not actually the ugliest in the whole world.

2. Nonplussed

The word “nonplussed” comes from Latin, and means “no more.” It’s used to mean a state of being where nothing more can be said or done, like when you are so confused by something you don’t know how to react.

Because of the negative prefix “non-,” though, people confused this word to mean “not surprised.” Both meanings became true over the years.

Meaning #1: Extremely surprised and confused.

He was nonplussed at seeing his cat chase the neighbor’s dog up a tree.

Meaning #2: Not surprised or affected at all (mostly used in American English).

The surprise birthday party left him nonplussed; he had known about it for a week already.

3. Left

Here’s a word you probably use all the time without realizing it’s contradictory! It’s the past tense of the verb “to leave.” When you leave your home, you are moving away from someplace. When you leave your keys at home, though, your keys are staying in one place.

Meaning #1: Departed, moved away from someplace.

He left his house at 6 in the morning to be on time for his flight.

Meaning #2: Remaining, something that’s not moved away.

He missed his flight because he had accidentally left his passport in his bedroom.

4. Refrain

The more commonly used meaning of this word is to stop yourself from doing something, like when you refrain from commenting on someone’s terrible shoes.

Another meaning, though, is the opposite: to do something over and over. The word comes from two different roots, so technically, it’s a homonym (two words that are spelled the same and sound the same but have different meanings).

Meaning #1: To stop yourself from doing something.

Please refrain from making noise during the concert.

Meaning #2: A line or phrase that is repeated in a song or poem.

The chorus, or the repeated part of a song, is called the refrain.

5. Bound

If your train is east-bound, it’s moving in the direction of east. If it’s bound to the station with ropes, it’s not moving anywhere at all. This is another case of homonyms being mistaken for the same word, as the two meanings have two different origins.

Meaning #1: Restrained and held in place.

He’s bound to his city because of his excellent job. I don’t think he’ll ever move away.

Meaning #2: Moving towards a destination.

She’s bound for college this weekend, so we’re loading up the car on Friday afternoon.

6. Overlook

If you take the word apart, you can see why “overlook” has two different meanings. When you look over something, you are either examining it closely, or you’re failing to see it.

The second meaning of the word comes from the 1500s, when people started using it to mean “to choose not to see something.”

Meaning #1: To supervise and watch over something.

His job is to overlook the construction site and make sure everyone remains safe.

Meaning #2: To neglect or fail to see something.

Because he overlooked a big safety hazard, the construction had to be started over.

7. Dust

To dust can mean to either remove dust, or add it. You might dust some sugar on a cake you’re baking, or dust the shelves to clean them. This is one case where context is really important!

Meaning #1: To add small particles to a surface.

The policemen dusted the crime scene for prints.

Meaning #2: To remove small particles from a surface.

My mother is a clean freak; she dusts our tables and shelves at least twice a day.

8. Custom

Something that is customary is normal and expected in a certain culture. Something that is custom-made is one of a kind.

How did these two different meanings come about? It might have been thanks to an Americanism (a word or slang term specific to America) that eventually got accepted into the language.

Meaning #1: Typical behavior exhibited by many in a society.

Taking off your shoes when entering the house is not only a custom, it’s also polite.

Meaning #2: Especially made, one of a kind.

This violin was custom-made for the famous violinist who has really small hands.

9. Either

The word “either” is an interesting one, since the definition we know the best is not entirely correct. The word comes from an Old English word that meant “both” or “each.” When we use the word to mean “both,” we are actually using it the way it was used originally.

Meaning #1: One or the other.

You can choose between eating either this chicken meal or that beef one.

Meaning #2: Both.

There’s traffic on either side of the road.

10. Original

When you have an original idea, it’s a new idea that no one has thought of before. But when you speak of something original, you might also be referring to something old that has existed for a while.

Surprisingly, both versions use the same meaning: Something original means it’s the first, whether it’s the first copy of a document, or the first great idea.

Meaning #1: Something old and unchanged.

I liked the original version of the movie better, not the remake.

Meaning #2: Something new and unique.

I had an original idea for a company, but I have no money to start it.

11. Hold up

This phrase actually has three meanings, but only two are contradictory. “To hold up” can mean to prevent something, or to support it. These meanings start to make sense when you consider the original definition of a hold-up: something used to hold a foundation in place, or to prevent a fall.

When you help someone through their troubles, you are holding them up (supporting them). When you stop someone from moving down a line, you are also holding them up (supporting the line from moving).

Technically, the phrase even has a fourth meaning: to rob a place, like a bank. You may have heard it used in a movie before, where the robbers “hold up the bank.” This means that the robbers prevented the bank from continuing its normal activities, but it’s a pretty specific case. You can also use the phrase as a noun to mean “robbery” (i.e. “This is a hold-up!”), but it’s outdated.

Meaning #1: To stay strong and continue despite troubles.

The tree held up to the rough hurricane winds, but the house was wrecked.

Meaning #2: To prevent something from continuing.

What’s the hold up? Can we please get going—I’m in a rush!

Bonus – Meaning #3: To literally hold something up, as an example.

He stood and held up his homework for the whole class to see.

12. Back up

“I’ve got your back!” That saying, which means “I’ll help you out,” can help explain why to back someone up means you support them. Or you might be literally backing up: moving away from something.

Meaning #1: To help or support someone by providing additional information.

If Ms. Smith doesn’t believe you when you tell her that your dog ate your homework, I’ll back you up. I’ll tell her how your dog chews on paper all the time!

Meaning #2: To retreat or move away.

I backed up slowly to get away from the growling dog.

13. Throw out

The key to understanding this phrase is the word “throw,” or the sometimes-used synonym “toss.” When you throw something, you are moving it away from yourself. That’s why throwing something out can mean to throw it into the garbage, or to throw it into the air for others to hear.

Meaning #1: To dispose of something, to put something in the garbage.

I threw out my old socks because they had holes in them.

Meaning #2: To suggest, to bring out a new idea.

When we had our brainstorming meeting, I threw out some new ideas that the boss liked.

14. Go off

The meaning of the word “off” is clear: closed, not working, the opposite of “on.” In British English, the phrase “to go off” can even be used to talk about food that’s gone bad or rotten.

On the other hand, an alarm or a bomb also “go off” when the alarm sounds or when the bomb explodes. This definition is actually limited to firearms or things that are “explosive” like guns, or your alarm clock’s explosion of sound that wakes you up.

Meaning #1: The word “off” on its own means to close, or stop working.

It’s really dark in my room at night when the light is off.

Meaning #2: The phrase “to go off” means to start or to turn on.

I didn’t hear my alarm when it went off this morning, so I was late to work.

15. Wound up

Before we had electricity, many things worked through gears. You had to wind up the gears to keep them running (the past tense is “wound up”). That’s why when someone is “wound up” (adjective), it’s like someone moved their gears to get them excited.

The verb “to wind” actually comes from the same root as “wander”: to move around or travel. That explains the third definition: When you wind up somewhere, you are ending your traveling and coming to a conclusion or a final place.

Meaning #1: To turn a knob or handle so something will work.

The last time I wound up my old clock was yesterday at noon. I have to wind it up every day or two, otherwise it stops working.

Meaning #2: To be excited or upset about something. (Informal adjective.)

The children will be completely wound up if you let them eat all of that candy today.

Meaning #3: To end up.

I originally thought I’d come back home, but I wound up staying at Sarah’s house last night.


It looks like we’ve wound up at the end of this post! Start using these words and phrases today, and the meanings won’t feel so difficult anymore.

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