man with glasses surprised at book

15 Difficult English Words: Definitions, Examples and Tips to Remember Them

They always somehow pop up. 

I’m talking about tricky English words, of course!

Some English words can even have different meanings depending on the situation.

In this post, I’ll show you 15 common but difficult English words and phrases, plus my favorite tricks for dealing with complicated English vocabulary.


15 Confusing English Vocabulary Terms

English is constantly changing as a language, and it can also have a lot of contradictions (ideas that are opposed to one another). Here are some English words with 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 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 use most often 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 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 has several meanings that can be contradictory. To hold up can mean to support something, or to prevent 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). You can also say that something held up, in the sense that it continued or lasted. 

But when you stop someone from moving down a line, you are holding them up (stopping 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.

Meaning #1: To support something so it doesn’t fall down.

We need more poles and ropes to hold up the tent. 

Meaning #2: To stay strong and continue despite troubles.

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

Meaning #3: To prevent something from continuing.

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

Bonus – Meaning #4: To rob a place like a bank.

The robbers held up the bank and left with all of the money.

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.”

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

You can also go off on someone and “explode” at them—not in a literal way, but through aggressive actions like yelling, criticizing or complaining a lot. 

Meaning #1: The word go off on its own means to close or stop working. It can even be used for food that’s gone bad or rotten. 

This stew went off quickly because you didn’t put it in the fridge. 

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.

Meaning #3: The phrase to go off on means behaving angrily and shouting at someone.

He was having a bad day and went off on me even though none of it was my fault.  

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” 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.

How to Learn Difficult Words in English

When you come across a difficult English word that you want to learn, here’s what you can do: 

Listen to catchy song lyrics

Some songs are naturally easy to remember because they’re fast-paced and easy to sing. You can take advantage of this for learning English vocabulary!

You can use a song lyrics search engine like to find songs that have a vocabulary word you’re trying to remember. Try reading along with the lyrics next time you listen to a song, or turn the subtitles on if you’re watching a music video.

An online immersion program may simplify the process. FluentU, for example, has music videos on its platform, along with movie trailers, TV show clips and other interesting English media.

Every video has interactive captions that let you instantly look up unfamiliar words and add them to a multimedia flashcard deck for further review:

english hard words

Here are a couple of difficult words that you can remember better with songs.


  • The word “millennial” means someone born roughly between the early 1980s and late 1990s. The 1975 song “Give Yourself a Try” uses this word in its lyrics (“I was 25… a Millennial that Baby Boomers like”):

  • “Oblivious” means to not be conscious or aware of someone or something. There’s a song that’s actually called “Oblivious,” and it uses the word repeatedly throughout the lyrics. The singer talks about wishing he was oblivious to the troubles he had in a difficult relationship:

Make associations with art 

​​When you catch yourself staring at a piece of art for a long period of time, whether it be in an art museum or online, that art is bound to stick in your mind. Associating difficult vocabulary terms with beautiful images is another way to help you remember them.

For the following words, we’ll use Leonardo da Vinci’s famous “Mona Lisa” painting to make our vocabulary associations. You can of course use any image that’s meaningful to you!


  • “Sustainable” means to be capable of being maintained or to be eco-friendly. Think of how “Mona Lisa” has sustained her mysterious smile for centuries! To remember the environmental aspect of this word, fix your mind on the green background behind her.
  • “Ecstasy” is a state of elated bliss, and it’s often used to describe extreme emotion. In contrast, Mona Lisa has a famously subdued, flat smile. You can imagine how different she would look if she were in ecstasy—mouth open, arms waving!

Describe your everyday routine

You know your everyday routine inside and out. There are objects you see every day, like your mirror or coffee pot. These are opportunities to create memorable associations for hard English words.

You can also use this exercise with younger children who want to learn hard English words.


  • “Supersede” means to take the place of something or someone that’s no longer useful. Think of the brand new electric toothbrush you have:

“For a very long time, I’ve been using a scratchy, cheap old toothbrush. Today, my new electric toothbrush arrived and superseded the old one.”

  • “Maintenance” means the upkeep of property or equipment, usually in reference to your home or belongings. You could talk about the oven you have to call your landlord to take care of:

“Today I called my apartment complex’s maintenance service to fix my oven, which I’ve been wanting to cook in for a very long time.”

Use context clues​

Let’s say you’re taking an English exam. No Wi-Fi, no dictionary. And you still don’t understand what the heck a word means.

There’s another way you can figure it out. Can you guess what it is?

If you thought of the answer context clues, you’ve already won the game!

Context clues might not get you the exact meaning of the word, but they do give you a strong hint or idea (in other words, a clue!).


  • “Commodity” means a product that can be bought or sold.

“In his job before, my grandpa was in charge of the commodities between his farm and one of the factories that still runs even to this day. He sold his vegetables, fruits and other crops, and the factory bought them from him so they could produce food.” 

From this passage, you can see that the commodities must be the same as the vegetables, fruits and other crops. You can figure out that they must be the products the narrator’s grandpa was selling.

  • “Recommend” means to express a good opinion of something or suggest something to someone else.

“My classmates recommended the new pizzeria that had just opened across the street. I took their suggestion and enjoyed it very much.”

We can see that it involves a suggestion between two people or groups of people, with positive associations.

Get a high-quality dictionary

At a restaurant and confused by a word on the menu? Not sure what that character just said in an English TV show?

You need a good English dictionary to help you quickly learn the hard words you encounter.

My favorite online dictionary is​, because it’s a great tool where you can get both the audio, definition and simplified outline of what the word means.

Compared to other dictionary apps or online dictionaries, this site breaks down what the word means in ways you can understand, whether you’re a beginner learner or a native speaker. It also gives you the option to see where the word can be found in other online resources.

Now you can use a dictionary to show off your vocabulary skills and boost your knowledge of hard English words every time you see one!


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

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