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The Hardest English Words to Learn?

The 8 Hardest English Words to Learn   English is not exactly the most “logical” language, something quickly realized by the multitudes around the world who study it. We talk about “rules” in English, but then have to spend more time talking about all the exceptions to those rules than we do for the language that follows the rule.

What are the hardest English words to learn? ‘Colonel’, ‘lieutenant’, and ‘rural’ perplex many with pronunciation, while grammar conundrums like ‘who’ vs ‘whom’ further complicate mastery.

We think we notice patterns in the way the language works, but then also meet countless examples of words that break the pattern. Frankly, most of it makes no sense, and it’s infuriating!  

In today’s article, we’re looking at what we feel are the 8 hardest English words (or word areas) to learn. When we say “hard”, we’re looking at words that:  

  • Are easily confused with other words of different meanings
  • Are difficult to spell or pronounce
  • Might be tricky to clearly define or explain

We look at the different types of words first and then give our ( opinion) some of the most difficult English words to learn. As you will see it is not all about how long these words are or how they are spelt – though we do have articles on that as well!

what are the Hardest English Words to Learn?

What Types of English words are hard to learn?

Homophones and Homonyms:

English is riddled with words that sound the same but carry different meanings or spellings, adding layers of complexity for learners and making them some of the hardest English words to learn.

Homophones, like “bare” (naked) and “bear” (the animal), and homonyms such as “lead” (to guide) and “lead” (a type of metal) can trip up even the most diligent student.

The issue arises in both written and spoken contexts, where the meaning can change based on spelling or usage.

While native speakers might navigate these words intuitively, learners require additional context or clarification to decipher the intended meaning, making mastery of these tricky terms an ongoing battle.

Phrasal Verbs:

A unique feature of English is its reliance on phrasal verbs, combinations of verbs and prepositions or adverbs that change the original verb’s meaning and make them some of the hardest English words to learn. .

Phrases like “run into” (meet unexpectedly) or “turn down” (to refuse) can confound English learners. The challenge? The meanings of these phrases often can’t be deduced by looking at the individual words.

Learners often have to memorize them, encountering unexpected interpretations in real-world scenarios.

To complicate things, some phrasal verbs can have multiple meanings, making them a dynamic and challenging aspect of the English language.

The Hardest English Words to Learn?

Idiomatic Expressions:

The rich tapestry of English idioms offers colorful ways to express ideas, but these can be mind-boggling for learners and produce some the hardest English words to learn.

Imagine trying to figure out “spill the beans” (reveal a secret) or “hit the hay” (go to sleep) based on literal translations! Idioms often emerge from cultural stories or historical events, which means their intrinsic meanings aren’t always obvious.

While they add flavor to the language, for those trying to learn English, they present a maze of hidden meanings that often requires explanation beyond a dictionary definition.

Words with Multiple Meanings:

English is sprinkled with words that, depending on context, can mean entirely different things. Consider “bark” (the sound a dog makes) vs. “bark” (the outer covering of a tree).

Such words pose a duality or sometimes multiplicity of meanings, making them puzzles for learners. This challenge extends beyond vocabulary to understanding the nuanced context in which the word is used.

It’s not just about knowing the word, but discerning its meaning in the surrounding conversational landscape, adding another layer of intricacy to the English learning journey.

Irregular Verbs:

The English language is notorious for its irregular verbs, which refuse to adhere to conventional past tense formations. Words like “drink” turning to “drank” and “go” becoming “went” can throw learners off course.

Instead of following the usual “-ed” ending for the past tense, these verbs mutate in seemingly unpredictable ways.

The inconsistency of these verbs forces learners to move beyond regular patterns and memorize each verb’s past form individually, an exercise both daunting and vital for achieving fluency.

The Hardest English Words to Learn?


Shortened forms of words or combinations, contractions like “it’s” (it is), “don’t” (do not), and “they’re” (they are) present challenges in both speech and writing.

The trouble arises when contractions sound similar to other words, such as “their” (possessive form) and “there” (indicating place). While native speakers might seamlessly switch between these in conversation, learners often grapple with the nuances, especially in written contexts.

Ensuring proper usage requires not just knowing the contraction, but fully grasping its distinct meaning and application.

False Friends:

Every language learner’s nemesis, false friends are words that look or sound similar in two languages but diverge in meaning. For English learners coming from Spanish, mistaking “actual” (current in English) for “actual” (real in Spanish) can lead to confusing exchanges.

Such deceptive similarities across languages create pitfalls where the learner thinks they’ve understood or used a term correctly, only to be met with puzzled looks.

Unraveling these misleading terms often demands a deeper cultural and linguistic understanding, making them particularly treacherous waters to navigate.

Unusual Letter Combinations:

Certain letter pairings in English, like the ‘gh’ in “through” or ‘ph’ in “phone”, produce sounds that might be foreign to many learners. These combinations can distort pronunciation and challenge the learner’s phonetic understanding.

Take “th” as an example; a sound unfamiliar in many languages, it turns simple words like “this” or “thing” into complex pronunciation exercises.

Such quirks demand learners not just to recognize letter combinations but to master the odd sounds they produce, adding to the rich tapestry of English learning challenges.

The Hardest English Words to Learn?

Most Difficult Words In English

1. Imply Vs. Infer

This one is a classic confusion that even manages to hoodwink many native speakers. The word “infer” refers to drawing a conclusion from evidence presented, whereas “imply” means to express or suggest something in an indirect way.

The most common mistake that learners seem to make is using “infer” when they mean “imply” rather than the other way around, for example:  

  • When you say that, are you inferring that I am somehow responsible for this?

2. Ensure Vs. Insure Vs. Assure

Here we have a three-way confusion with words that all sound quite similar, especially when spoken at speed.

It’s no wonder that learners of English struggle with these and struggle to use them in the right contexts.

Here’s a quick summary of the correct meanings and usage:  

  • Ensure — to guarantee that something will happen
  • Insure — to protect against liability, damage, etc.
  • Assure — to give confidence to (esp. while trying to convince someone)

  From these definitions, “insure” is the standout among them with a very different meaning, but “ensure” and “assure” clearly have some overlap.

For learners, they can think of them like this: “ensure” is used to refer to actions, guaranteeing that actions will be taken or things accomplished; “assure” is more of a spoken term to give the listener more confidence in what the speaker is saying.  

  • We need to insure the car against theft and damage
  • We will take all steps necessary to ensure the success of the project.
  • I assure you, I will be there on time.

3. Complimentary Vs. Complementary

The words “complimentary” and “complementary” are another example of words that even native speakers tend to get wrong.

The interesting thing here is that while the spellings are very close — only one vowel apart — the definitions are quite different:  

  • Complimentary has two meanings: (1) words or expressions said to praise or speak positively about something, and (2) free of charge
  • Complementary: fitting or suitable to the extent that it enhances other existing positive qualities or features

  The two also can be used as verbs “compliment” and “complement”, but it should be noted that when used as verbs, the second meaning of “complimentary” no longer applies.

Here’s how we might use them in sentences:  

  • He was very complimentary about my new dress
  • He said that my new dress complements my figure and facial features
  • The furniture in this room is very complementary to the overall tone of the decor

4. Literally

The word “literally” has become quite contentious in the English-speaking world, and one result of that is creating a lot of confusion for English learners.

Those for whom English is not their native language may look up the word “literally” in the dictionary and think they’ve mastered the meaning, but then when they hear native speakers using it in 2023, they might get seriously confused.  

  • Original (from dictionary): exactly as stated; in a literal manner
  • Modern (informal): used for emphasis, but not exactly as stated

  You see how the two uses have become opposite? The word “literally” has become a contronym (a word with two meanings that are opposite to each other).

It therefore has become a hard word for ESL learners because they will most likely only cover the original, dictionary-based meaning in their own lessons, and might miss the other, leading to confusion as and when they encounter native speakers using the word figuratively.

5. Whom

Should we use “who” or “whom”? We are traditionally told to distinguish these words by remembering that:  

  • “Who” is used to refer the subject of the sentence
  • “Whom” is used to refer to the object of the sentence

But for some, this explanation just leaves more questions. So, there is another way in which one can overcome the confusion, and that is to remember this instead:  

  • If the “who/whom” could be replaced with an subject pronoun (he/she), then we should use “who”
  • If the “who/whom” could be replaced with an object pronoun (him/her), then we should use “whom”


  • And you are going with whom? I am going with her — object pronoun, so “whom”
  • Who is your sister? She is my sister — subject pronoun, so “who”
The Hardest English Words to Learn?

6. Colonel & Lieutenant

Now we come to words that are just plain difficult to pronounce, and understand why they are pronounced as they are.

Both of these military ranks are particularly confusing for English learners because of their combinations of silent letters, and even differing pronunciations between different forms of English.  

In “Colonel”, for example, the first ‘l’ is not pronounced, making it more like “kernel” when said aloud. What’s more, if learners hear this word in its original French, they will hear the first ‘l’ pronounced, making it “ko-lo-nel”.

The word is originally derived from the 16th century French word “Coronelle” which referred to a regiment commander in the army.   As for “lieutenant”, it depends on which variant of English you are hearing, US or UK English.

The US pronunciation follows the original French more closely, “loo-tenant” whereas the UK English version inexplicably changes the first syllable to “leff-tenant”. For ESL learners and Native speakers these differences are confusing, even baffling.

7. Rural

When students come to talk about towns/cities and the countryside, the terms “urban” and “rural” are bound to emerge.

The former doesn’t tend to present much difficulty, “err-bun”, but the latter can be tricky for many speakers for whom the ‘r’ sound is not common in their own language.

ESL learners from many east Asian countries, for instance, find this word something of a tongue twister.

8. Sixth

This is a word that some native speakers might wonder why it’s so hard to pronounce, but in doing so fail to appreciate just how intricate the word really is.

When you break down the pronunciation, you start to see just how many tricky things are happening, in particular the transition between ‘x’ and ‘th’.

This is extremely tricky for many non-native speakers, especially as ‘th’ is a construction that not many languages use. Words that only use ‘th’ are hard enough for some, but throwing the ‘x’ in first makes it even harder.  


From puzzling homophones and deceptive false friends to the unpredictable nature of irregular verbs and the complexity of idiomatic expressions, the journey to mastering the language is rife with hurdles.

Yet, it’s these very intricacies that enrich the English language, making it a captivating puzzle for those dedicated to its study.

While the path might be strewn with obstacles, the rewards of fluency and the joy of understanding its nuances offer a gratifying payoff for every intrepid learner.


I have been a teacher of English for over 15 years, in that time i made hundreds and thousands of resources and learnt so much i think its worth sharing. Hopefully to help teachers and parents around the world.

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