The following is a true story about if vs whether grammar pitfalls that can happen in business communications.

The First Email

A few weeks ago, one of the leaders of the company I work for sent all employees an email announcing an upcoming company event and listing possible dates on which it might be held. The leader also wrote this:

“Please let me know if you have any known conflicts.”

This sentence, being an “if statement,” is equivalent to the following:

This type of statement expresses a logical condition. If this, then that. Conditional statements say nothing about instances in which the condition is false, only about instances in which the condition is true.

I checked my calendar and ascertained that I did not have any known conflicts. Thus—according to the grammar of the sentence—the rest of the statement (about letting the leader know) did not apply. I figured that the leader did not want an inbox full of emails saying “I have no known conflicts.” The leader wanted to know only about cases in which there were conflicts, thus avoiding superfluous emails.

So I did not reply. I wasn’t—I swear!—just pretending not to understand the sentence, to prove what an awesomely fastidious grammar queen I am. I really thought I was doing what was wanted of me.

The Second Email

A week later, the leader sent out a second email:

“Just a reminder that we would like to know if you have any known conflicts. . . . If you’ve already replied – thanks and no need to send again.”

Like the sentence in the first email, these sentences, grammatically, indicate conditions:

I did not have any known conflicts, so the rest of the first sentence did not apply to me. I also had not already replied, so the rest of the second sentence did not apply to me, either. Strictly speaking, then, there was no need to reply.

Analysis: Should the Leader Have Used If or Whether?

However, being the twenty-first-century English speaker that I am, I know that the word if is commonly colloquially used in place of the word whether. Unlike if, which indicates that there is a condition with only one option (only one “then” to follow the “if”), whether indicates that there are two options (and does not indicate a condition).

If the leader had, in fact, mistakenly used if instead of whether, the sentence in the first email would be equivalent to this:

This statement is not conditional, and it indicates two options. No matter which instance is true—whether I have any known conflicts or don’t have any known conflicts—I should let the leader know.

The second email is trickier. If the leader had mistakenly used if instead of whether in both sentences, we would get this:

The first statement expresses the same thing as in the first email when if was changed to whether (i.e., I should reply no matter what). The second statement does not make sense. If you have not already replied, it is not possible to do so again. This statement doesn’t make sense because the leader was expressing a condition, and so if was, indeed, the correct word choice. To avoid confusion, whether technically should have been chosen in the other two sentences—that is, if the leader did not intend to express a condition, but rather two options.

That was the conclusion I came to, anyway, upon receiving the second email. So I replied. I guess that was an appropriate response, since the leader wrote back to me with “Thank you!”

Note for the Record

I did not, while reading the emails and deciding whether to respond, have intricate thoughts about conditional statements, two options, and so on; my thoughts and actions happened more organically than that. It was only in writing this blog post that I was able to piece together the exact grammatical reasoning behind my comprehension (or lack thereof!) of the emails.

A Little If vs Whether Grammar Quiz

Here’s a little if vs whether grammar quiz. In the following grammatically correct sentence, what is the conditional statement? What is the statement that is not conditional and indicates two options?

I was stumped by yet another medical mystery.

I have been plagued by migraine headaches for my whole life. My triggers include too much sunlight or sunlight from certain angles; overheating; too much alcohol; dehydration; not enough sleep; too much jostling while traveling by car, bus, train, plane, boat, roller coaster, horse and buggy, etc.; jostling from too much coughing; and vomiting for any reason. (Apologies if that was too graphic for you. . . . If it was, you may wish to stop reading.)

These migraines are no small deal. They leave me moaning in bed in severe pain. And they last ten days: exactly ten days, no matter what I do, diminishing in severity during that time. Luckily, I get them only a few times per year. Unluckily, they are debilitating, causing me to miss work, social engagements, and regular life activities; and they are extremely unpleasant.

(And people wonder why I don’t like to travel! Have you ever been stuck in a New York City hotel with a ten-day migraine?)

My usual medicine for migraines is ibuprofen. Lots of ibuprofen. 800 mg, 4 times a day, for 10 days. This allows me to return to work within a day or two, though at that point I still have frequent intervals during which I need to lie down.

Having heard about other medicines on the market, I asked my doctor about my options. Over a period of a year or two, she recommended a series of drugs, all in the triptan family: rizatriptan, sumatriptan, etc. I must have tried them all. But I could not keep a single one of them down. Within half an hour to an hour of taking a pill, I would acquire a level 10—maximum strength!!—headache, vomit the pill up, and stagger off to bed for the next several days.

Finally, after completing the brutal rounds of the triptans, my doctor recommended magnesium supplements. In previous months, I had taken a daily magnesium pill, but it did not seem to have any effect. However, my doctor explained that magnesium is not always absorbed well by the body, and some supplement formulations work significantly better than others.

Upon hearing this, I scampered off to the Internet. There, I read that, indeed, some magnesium pills are nearly useless because the body does not absorb the mineral. Yikes! I decided to try, instead of a pill, a powder that I mix with water. The manufacturer claims that the magnesium in this powder is in an easily digestible form.

Well, and guess what? I have not suffered from a ten-day migraine attack—knock on wood!—since beginning this daily powder supplement regimen, which was many months ago. (When I feel a headache coming on, I still reach for my ibuprofen standby and pop those pills as soon as possible, along with half a slice of bread so they are absorbed. This has happened several times in the past few months, but none of these twinges have developed into a full-blown attack—knock on more wood!)

This solution may not work for everyone. Everybody’s body is different. But perhaps it will help someone out there; and so I share my story.*

But anyway, here’s the main medical mystery here: why on earth didn’t my doctor share the magnesium idea first, before hitting me up with the hard stuff?

(I have some guesses as to the answer, and none of them are pretty. Fortunately, though, you stopped reading back at the second paragraph, so you will not be filled with desperation at the suggestion of pharmaceutical companies’ mighty, and powerfully complex, hold over physicians (see, for example, this article about human tendencies toward reciprocal gift giving); or patients who insist on the hard stuff, and as much of it as possible, and are offended by attempts to seek more natural solutions. . . .)

*Please be so good as to refer to the footnote in my original Medical Mysteries post.

The inquisitive one exchanged a few messages with someone cute on a dating app. The person’s profile mentioned art collecting; co-ed, pick-up soccer; and creating sculptures out of acorns, old car parts, and toenail clippings. They decided to meet at a bar in the city, the next day after work.

The inquisitive one arrived at the bar and sat on a stool next to the date. The date’s face, neck, and arms were coated in a thick layer of sweat. The sweat glistened in the dim lights of the bar.

“I was almost late getting here,” said the date. “Things got crazy at the end of my work day. I scrambled to finish everything. Then I had to ride four Metro lines and take three buses to get here. And I had to run the last two miles on foot. But luckily I wasn’t late. I hate tardiness!”

“Oh,” said the inquisitive one.

“What do you like to do for fun?” said the date.

“Well,” said the inquisitive one, “I enjoy running and hiking. Sometimes I see strange things in the forest. And sometimes strange things happen. Then I think about them. Some might not think these things are strange at all, but I do.”

“Oh,” said the date.

“What do you like to do for fun?” said the inquisitive one.

For some reason, the date started talking about hot peppers. That was when they discovered they both had an interest in growing, cooking, and eating hot peppers. The bartender brought wine, and they talked about the intricacies of hot peppers until the wine was all drunk.

That’s when the date said, “I should tell you something.”

“What?” said the inquisitive one.

“See, my job is very important and top secret. I’m about to be sent to Asia for work. I probably won’t be back for a few years. I can’t tell you anything more, because it’s classified.”

“Oh,” said the inquisitive one.

They said good night and went their separate ways.

And then, two days later, they followed each other on Instagram, Twitter, and Pinterest.

Which of these photos, in your opinion, best represents happiness? The daisies or the rainbows?

Okay, I admit it—this is a trick question (and a silly one, at that). According to Mark Manson in his book The Subtle Art of Not Giving a F*ck, neither is a good representation of happiness. Why not?

“Because happiness requires struggle. It grows from problems. Joy doesn’t just sprout out of the ground like daisies and rainbows. Real, serious, lifelong fulfillment and meaning have to be earned . . .”

However, maybe daisies and rainbows can be representations of happiness, if we think of them like this:

Imagine working very hard to clear a patch of land, till it, add compost, plant seeds, water them diligently, and prevent the seedlings from being damaged by winds or floods or weeds or animals, to finally produce beautiful flowers—only to have to work to keep them looking lovely as long as possible, upon which they die and you must begin again.

Or envision undertaking a long, hard voyage through the wilderness, staving off thirst and hunger and insects and unsociable animals, and experiencing inclement weather, including a long and hard rainstorm, to finally be able to witness an idyllic scene—upon which the double rainbow vanishes almost immediately, and you are still in the middle of the harsh natural world and must continue to work to survive.

But don’t worry—there’s good news. There’s no need to resign yourself to a life of grunt work and misery. According to Manson, the key is to choose a struggle that you enjoy. If you enjoy gardening, working hard to grow beautiful flowers is your happiness. If you enjoy hiking or boating through wilderness areas, striving to witness idyllic rainbow scenes is your happiness. To experience joy, ironically, we must choose our struggle.

What’s yours?

The boss said to the inquisitive one, “How’s it going with the thingamajig project? Will the thingamajig you’ve been working on be complete by Thursday?”

“The thingamajig project is going great,” replied the inquisitive one. “Yes, I will have the thingamajig ready for you by Thursday.”

“Great,” said the boss. “The thingamajig is very important.”

“I agree with you about the importance of the thingamajig,” replied the inquisitive one.

So then the inquisitive one resumed working on that one thing, and on Thursday the boss was pleased.