“Would’ve, could’ve, should’ve” — this regretful refrain reflects on past actions, choices, or opportunities, suggesting that someone would have, could have, or should have done something differently. We love to use contractions in English, especially in casual conversation, which is why the expression is styled as such. However, the regular use of “should’ve” to represent “should have” has resulted in one of the most common and unfortunate grammar gaffes in the English language: “should of.” 

We’ve all heard or seen it in action: “I should of called sooner” or “They should of known better.” This pairing — “should of” — is never correct, so how did this unwelcome imposter become so widespread? Grammarians believe it comes down to the pronunciation of the contraction “should’ve,” which sounds nearly identical to “should of,” causing this slip-up to become a permanent fixture in colloquial conversation. The mistake is often imperceptible in spoken conversation and is better caught in writing. Merriam-Webster dates the usage of the contraction “should’ve” to the mid-19th century, suggesting that “should of” has likely been around just as long. Its counterparts, “would of” and “could of,” are similarly confused and are also incorrect.

So, why is “should of” deemed incorrect? It boils down to grammar rules and the appropriate sentence structure of English verbs. Verb phrases are made of one or more auxiliary verbs and a main verb. “Would,” “could,” and “should” are auxiliary verbs — also called “helping verbs” — and they require another auxiliary verb or a main verb (or both) to follow them in order to form a correct verb phrase. “Have” can function as an auxiliary verb, but “of” cannot — it is a preposition. Consider the example “I would have called sooner,” which includes the correct verb phrase “would have called” — no “of” here.

Interestingly, The Merriam-Webster entry for “of” lists it as a preposition (and rightfully so), but has added another part of speech: auxiliary verb. Does that mean “should of, would of, could of” IS correct? Not so fast. It’s listed as a nonstandard version of “have” and defined as being “​​used in place of the contraction ‘ve often in representations of uneducated speech.”

Dictionaries record the ways people use language, but they don’t dictate the rules of grammar. On this point we’ll remain grammar sticklers and say “should’ve” should always be used instead of “should of.” 

I don’t claim grammatical authority, but if I may humbly make one recommendation, I move to retire the use of “whom” — or at least stop reprimanding writers who’d prefer to use “who.” I’m not the first to suggest this; even Merriam-Webster notes that the demise of “whom” has been discussed by scholars since 1870. Many proponents of the discontinuation of “whom” point out that in most cases, “who” can take the place of “whom,” rendering the latter redundant. I agree that while “whom” sounds charming when used properly, it’s largely impractical.

To understand the fuss, let’s revisit the respective functions of “whom” and “who.” “Whom” is an object pronoun — much like “him,” “her,” or “me” — as seen in the example, “Whom did you see?” in which the subject is “you” and “whom” is the object of the verb “see.” On the other hand, “who” is used as a subject pronoun, akin to “I,” “he,” or “she.” For instance, “who” is the subject in the sentence, “Who was elected?” 

Although this grammatical practice has endured for centuries, there’s now a tendency to excessively police the usage of “whom”/”who,” resulting in a linguistic landmine that causes distress to students, writers, and professionals who (erm — or is it whom? — no, definitely who) agonize over which one is correct. 

Understandably, many people would rather do away with this grammatical dilemma, so “who” has begun replacing “whom” in casual conversation. “Who” feels more informal and intuitive in most scenarios. “Who did you see?” rolls off the tongue far more naturally than its technically correct counterpart. In a modern world that values fast, efficient communication over correctness, “who” often prevails.

With that said, a few reasonable arguments persist in favor of “whom.” The classic prepositional constructions “with whom,” “to whom,” or “from whom” have a rhythmic quality that can’t be adequately replaced by “who.” In these situations, you always have the option of rephrasing. For example, instead of asking someone, “With whom are you traveling?” you might rephrase and say, “Who are you traveling with?” because it feels more natural. This may make your high school English teacher cringe, but it’s what most people would actually say in casual conversation. (And we’re on the side of breaking the rule against ending sentences with prepositions.) 

But before we officially send “whom” off on its farewell tour, we should note that the word seems to have developed another application as part of a new phrase: “whom of which.” It’s used like so: “My ethics professor, whom of which is my favorite teacher, writes many books.” In 2023, MIT linguistics professor David Pesetsky described the phrase as “brand new,” “very colloquial,” and “extremely law-governed.” Respectfully, I will be abstaining from this curious new construction — after all, do we really need another tangled usage of “whom” to debate?

Recently I was chatting with a friend about our favorite morning beverages, comparing the qualities of espresso, lattes, matcha, and tea. As the conversation unfolded, I noticed we freely alternated between “different from” and “different than” without a second thought. For instance, I said, “Matcha is different from regular green tea,” while my friend declared, “An Americano definitely tastes different than a regular coffee.” With our coffee and tea preferences settled, the grammar nerd in me was left wondering: Which of these phrases is grammatically correct?

It turns out that “different from” is the more formal and universally accepted phrase. If you aim to please style guides, it’s the safer choice. The statement “sympathy is different from empathy” flows naturally. However, “different from” isn’t the only acceptable variation; “different than” and “different to” have been around for centuries, each with its own set of nuances.

“Different to,” as in, “Her approach to the issue was different to mine,” is most often used in British English. It’s best reserved for informal situations, in the same way that its American counterpart, “different than,” should be treated. 

According to Merriam-Webster, “different than” got a bad rap in the 19th century when grammarians adopted a little-known guideline stating that “than” should only be used following a comparative adjective showing a higher or lower quality or degree, such as “taller” or “worse.” Following that rule, the correct usage of “than” is “My brother is taller than my sister but shorter than my dad.” However, “different” can function as a comparative adjective, which is why it might feel more natural to use “than” instead of “from,” as seen in the example, “The second book was different than the first — it had a much darker tone.”

So, where does this leave us? Although “different than” has been shunned by grammar purists for centuries, it’s perfectly acceptable to use, especially in informal language. However, for those bound to formal writing conventions or style guides, “different from” remains the go-to choice in American English.

A sentence without appropriate punctuation is like a highway without road signs — it still technically functions on a basic level, but it lacks clarity. Using punctuation properly can be tricky, though, and common errors, from comma splices to misused semicolons, can make writing feel disjointed. Even the most seasoned writers fall victim to these mistakes. Fortunately, there are some practical guidelines and tips for avoiding punctuation errors and ensuring clear, coherent communication.

A comma splice occurs when two independent clauses are linked by a comma without a conjunction. Consider this example: “I went to the library, I found the book I was looking for.” If both segments of the sentence can stand alone as a complete sentence, as in this case, it’s a comma splice.

The easiest way to fix this is to add a conjunction, a word that links the clauses. You might fix the aforementioned sentence by saying, “I went to the library, and I found the book I was looking for.” Throwing in a coordinating conjunction is typically a safe bet. These are easy to remember using the acronym FANBOYS (for, and, nor, but, or, yet, so). 

If a conjunction doesn’t work in the context or tone of your sentence, you can change the comma to a semicolon, which is made for linking independent clauses: “I went to the library; I found the book I was looking for.” If none of these options seems appropriate, simply split your clauses into two separate sentences.

While commas are essential to use before conjunctions that connect two independent clauses, a comma isn’t necessary if one of the clauses is dependent. This requires knowing the difference between independent clauses (those that can stand alone as complete sentences) and dependent (or incomplete) clauses that cannot stand alone. 

Consider this incorrect example: “I went to the gym, after I finished my work.” The latter clause is dependent (or incomplete) because “after I finished my work” cannot stand alone as a sentence, so the comma between clauses is unnecessary. The correct way to format this sentence is, “I went to the gym after I finished my work.”

​​Hyphens are useful for compound modifiers used before a noun, e.g., “well-known,” “high-quality,” “state-of-the-art.” However, you don’t need the hyphen if one of the words in the compound modifier is an adverb that ends in the suffix “-ly,” such as “loudly,” “quickly,” or “extremely.” 

This rule is why you won’t find hyphens in compound modifiers such as “highly respected” and “deeply rooted.” A few other adverbs also shouldn’t be hyphenated when used as a modifier, including “very,” “most,” and “too.” Some incorrect examples include “very-talented,” “most-wanted,” and “too-kind.” Instead, drop the hyphen and leave a space between the modifying words. 

These similar-looking punctuation marks are often mixed up, but here’s how to tell them apart. A semicolon essentially acts as a bridge joining two related clauses, as seen in the comma splice fix we looked at earlier. Here’s another example: “I went to the dentist; she gave me a good report.” This punctuation mark also has one other job: separating items in a list if the items themselves require commas. For example: “I’ve visited London, England; Dublin, Ireland; and Athens, Greece.” The semicolon provides a more significant delineation where throwing in additional commas would cause confusion.

Colons have more functions than semicolons. They’re used to introduce lists, explanations, and quotations, or to emphasize a particular idea. They often precede information set up in the first clause. For example, “She had one goal: to finish her first marathon before she turned 30.” This sentence uses a colon to create a pause and add emphasis. Colons can also be used to list things, as in, “I need three things on Monday morning: coffee, headphones, and more coffee.” However, if the word before the list is a verb or preposition, a colon isn’t necessary. For instance, “My favorite holidays are Christmas, St. Patrick’s Day, and Halloween” does not require a colon.

Another rule to keep in mind is that a colon must be preceded by an independent clause (a stand-alone sentence). Consider the incorrect example, “Her worry was: the deadline was quickly approaching.” The correct colon usage in this case is: “She had one worry: the quickly approaching deadline.” Finally, if the clause following the colon is dependent (as seen in the last example), the first word does not need to be capitalized. However, if the clause is independent (a complete sentence on its own), it should be capitalized, as seen in the example, “She had one worry: The deadline was quickly approaching.” 

As if English wasn’t complicated enough, it also features dashes of three different lengths that can significantly alter words and sentences. The shortest dash, the hyphen (-), is the most common. It’s used to create compound words such as “sister-in-law” or  modifiers including “clean-cut” and “well-dressed.” 

The em dash (—), the longest of the three, is the second most common. It functions as a pause, and depending on your goal, it can replace a comma, a colon, or parentheses. It’s used to set off extra information, as in, “The concert — though highly anticipated — ended early due to weather concerns.” It can also add emphasis: “The choice was clear — leave now or stay forever.” Whether or not to use spaces around the em dash depends on the specific style guide to which you adhere.

The en dash (–) is the least used of the three dashes. In standard American English, it indicates a range between numbers, as in, “pages 40–55,” and it replaces the word “to” in statements such as, “I took the New York–Los Angeles red-eye.” Interestingly, in British English, it sometimes performs the job of an em dash, creating a break to emphasize additional information.

With so many punctuation rules and nuances, it’s no wonder things can quickly get confusing. If you struggle with any of these errors, rest assured you’re not the only one. Knowing the tips and tricks to avoid them will elevate your writing and leave a lasting impression on your reader(s).