Top 10 trickiest punctuation rules for English learners

Most English learners don’t struggle much with the basics of English punctuation. You probably already know, for example, that a sentence ends with a period, a question ends with a question mark, and an exclamation point shows excitement.

But then there are some punctuation rules that English learners (and even native English speakers) find trickier! When should you use an apostrophe? When should you capitalize and not capitalize words like east or president? When should you use a semicolon ( ; )?

In this post, we’ll answer all those questions and more! Let’s read on to see the top 10 trickiest punctuation rules in English (and how you can master all of them!)

The misuse of an apostrophe ( ’ ) is probably one of the most common errors in English! Here are the situations where we need to use an apostrophe:

• To create a contraction (the apostrophe replaces the missing letters):

  • It is raining today. → It’s raining today.

  • We are leaving. → We’re leaving.

• Forming possessive nouns:

  • the teacher’s desk
  • the cats’ bed
  • Ryan’s car

And here are situations where we don’t use an apostrophe:

• Before the plural -s:

  • ✅ I have two dogs.
    ❌ I have two dog's.
  • ✅ We’re eating dinner with the Smiths today.
    ❌ We’re eating dinner with the Smith’s today.

• Possessive adjectives (its, his)

  • ✅ The kitten opened its eyes.
    ❌ The kitten opened it's eyes.

• Possessive pronouns (yours, his, hers, ours, theirs):

  • ✅ This food is ours and that food is yours.
    ❌ This food is our’s and that food is your’s.

Imagine you’re writing the most interesting, amazing story, and it’s finally time for the main character to confess their love! But as you’re writing your dialogue within quotation marks ( “ ” ), you realize: you don’t know where the punctuation goes in relation to the quotation marks!

That’s okay, there are three easy rules to help you figure this out:

1. If there’s a subject and reporting verb before the quotation marks, add a comma directly after the reporting verb (but not inside the quotation marks):

   John confessed, “I love you.”

2. All other punctuation marks should go inside quotation marks.

   • John confessed, “I love you.”
   • “Do you know where the library is?” Elaine asked.
   • My mom yelled, “Don’t eat those, they’re for the bake sale!” when we tried to eat the freshly baked cookies.

3. When you’re using quotation marks around a statement, and the quote is not the end of the sentence, use a comma rather than a period:

   “I love you,” John confessed.

   You can use a period if the quote comes at the end:

   John confessed, “I love you.”

   And a quote that ends in an exclamation mark or a question mark will keep it, even if it’s not at the end of the sentence (see examples above).

In English, we almost always capitalize proper nouns, which are specific names for something. Sometimes it can be difficult to figure out which nouns are proper and which nouns are common (and don’t get capitalized). Here’s a quick list to help you out:

• Names of people (e.g. Sarah, Michael, the Smiths, Marco Polo, ...)

• Names of places (e.g. China, The Mississippi River, The Bronx, Central Park, ...)

• Days, months, and formal holidays (e.g. Monday, February, Halloween, ...)

• Titles of people (e.g. President Obama, Dr. Smith, King Charles, ...)

• Company names (e.g. Google, Starbucks, Menards, ...)

• Titles of books, movies, and art (e.g. Starry Night, A Christmas Carol, Goodnight Moon, ...)

• Religions and philosophies (e.g. Impressionism, Buddhism, Democracy, ...)

A few tips to help you out with tricky cases:

• When you are capitalizing a long phrase (e.g. a long book title) always capitalize the first word and all of the content words (nouns, verbs, adjectives, adverbs). Function words (articles, prepositions, etc.) are usually not capitalized. For example:

  The Curious Incident of the Dog in the Night-Time

• Some words are only capitalized when they are part of a name. For example:

  • I met Professor Mason. I met the professor.
  • I traveled the American South. I traveled south.
  • I used Google to find an answer. I googled the answer.

If you want to learn more about capitalizing these words, check out our post on common and proper nouns in English!

Another common confusion for English learners is where exactly to put a comma ( , ) in a list or with conjunctions (e.g. because, and, or, ...). Let’s take a quick look at these!

We use commas to separate words in a list of three or more when there is no linking word to connect the items in the list. For example:

• We traveled to Europe and visited London, Paris, Berlin, and Rome.
• The small, cute, fuzzy kittens wanted to sit on my lap.

We also use commas when connecting two independent clauses with a coordinating conjunction (such as and or but). The comma goes before the coordinating conjunction:

• I wanted Italian food for dinner, but my parents chose a Mexican restaurant.
• Rachel mowed her lawn today, and tomorrow she’ll start planting the garden.
• We can go see a movie, or we can stay home and play a game.

Commas are also used between a subordinate clause and the main clause, if the subordinate clause comes first:

Occasionally you will see a comma before a subordinate clause as well but this is optional. Check out our post on conjunctions in English to start learning more!

Commas are also used around certain relative clauses (which describe nouns), called “non-defining relative clauses.”

Check out our post on relative clauses in English to learn more.

Commas ( , ), semicolons ( ; ), and em dashes ( — ) are all used to join two clauses together, but what’s the difference between them? Let’s take a look!

• A comma is used to connect two independent clauses with a coordinating conjunction, or it is used at the end of a subordinate clause that comes before the main clause in the sentence:

  coordinating conjunctionsubordinate clause

  Today I’m going to paint the office, and tomorrow we can put the new desk in there.

  After we put the new desk in the office, we will build the bookcase.

• A semicolon is used between two related independent clauses that are not joined by a conjunction.

  • We can study for the exam in the library; there are many individual study rooms you can book.
  • My parents are taking my little sister to the zoo today; it’s her birthday and she loves animals.

• An em dash is like a chameleon because it can be used in place of other punctuation — namely parentheses and commas. When a sentence is getting long and complicated, you can use a dash around a clause to indicate that it’s additional information, and make a clause easier to understand.

  • The guy who shares my office — he just started working here a couple weeks ago and is still getting used to the office culture — keeps having long, loud conversations on the phone and it’s driving me crazy.
  • My parents are taking my little sister to the zoo today; it’s her birthday and she loves animals.

Oh look, more commas! Commas tend to be confusing for even native speakers of English, so it’s no wonder that they’re so hard for English learners to figure out!

Sometimes we start a sentence with an introductory phrase, either a participle phrase (a phrase starting with a participle) or an adverbial phrase (a group of words that acts as an adverb). It’s common to put a comma after these phrases:

Sometimes it’s optional to add this comma, especially after a single word. But if you think a reader might be confused, add the comma:

Parentheses ( ) are a common type of punctuation in English, but how do you use them? Here are the important things to remember about parentheses:

• Parentheses always come in pairs! You should always start a pair of parentheses with the one that curves to the right → ( and finish with the one that curves to the left → )

• Parentheses typically contain additional or non-essential information. This information is usually used to further explain something already mentioned in the sentence

  • A tornado (the fourth one this year) touched down near the city park.
  • If the weather is nice this weekend, we’re going to go camping (I’d rather stay in a cabin though).

• If the information inside a pair of parentheses is a question or exclamation, you can add the appropriate punctuation:

  • My sister (who just got promoted at work!) invited all her friends on a birthday vacation.
  • I always loved going to that little ice cream shop on the corner (is it even open in the winter time?).

The colon ( : ) and the semicolon ( ; ) share a similar name, but do they have a similar purpose? They are both used to separate parts of a sentence, but besides that they have different purposes. Let’s look!

Here are the uses of colons:

• to introduce lists of items:

  I gathered all the ingredients for the pie: apples, butter, flour, sugar, and cinnamon.

• to introduce one example or a phrase that is not a complete clause:

  My daughter only wanted one thing for her birthday: a pet cat.

• between the hours and the minutes, when giving a time:

  Steven logged into work at 8:57am.

Semicolons are mostly used to join two independent clauses that are related, but not joined by a coordinating conjunction:

• The cat likes to sleep on the couch; the dog prefers sleeping on the bed.
  We traveled to Greece for vacation; we visited Santorini, Corfu, and Mykonos.

Have you ever seen someone use three periods in a row like this…and been confused about what that means? This punctuation is known as an ellipsis ( … ), and it has four main uses:

1. Pausing for dramatic effect:

   And after all that effort… I only got a C on my project!

2. Trailing off into silence or leaving a thought unfinished:

   I don’t know…

3. To suggest that there’s more:

   To be continued...

4. To show that words in a quote have been omitted (this is common in formal writing):

   Original quote:

   “Why then is not every geological formation and every stratum full of such intermediate links? Geology assuredly does not reveal any such finely graduated organic chain; and this, perhaps, is the most obvious and serious objection which can be urged against the theory. The explanation lies, as I believe, in the extreme imperfection of the geological record.”

   Charles Darwin, The Origin of Species

   Shortened quote:

   “Why then is not every geological formation and every stratum full of such intermediate links? … The explanation lies, as I believe, in the extreme imperfection of the geological record.”

   Charles Darwin, The Origin of Species

So you already know that exclamation points ( ! ) are used to mark a command (Stop!), an exclamation (Wow!) or to show excitement or emphasis in a statement (It’s great to see you!)

In formal writing, like workplace emails, you will often also see exclamation points used to make your tone sound cheerful, friendly, or helpful:

In informal writing, such as text messages, internet comments, or talking with friends and family members, people will use multiple exclamation points that relate to how much emotion they’re feeling:

• I can’t wait to see you tomorrow!!!
• Omg you got engaged? YAY!!!!!!!!!!!!

In informal writing you can also combine an exclamation point with a question mark to show shocked confusion:

If you’re unsure of how many exclamation points to use, it’s always okay to use just one in any situation where you want to show excitement or strong emotion.

Punctuation can be a little tricky in English, but by breaking it down into these ten simple distinctions, you can easily master English punctuation!

Remember, if you’re trying to tackle a tricky punctuation problem, think about what message you’re trying to convey, and how that message might be interpreted depending on the punctuation you use. You can always consult a trusted punctuation guide (like Mango Languages!), or ask a friend or colleague to help you out.

If you’re ready for some extra practice, check out our capitalization and punctuation activities!