The Battle of Who Could Care Less

If you’re reading this blog, it’s because you care about words and the myriad ways they can be strung together into stories. You may even have a grammatical, idiomatic, or linguistic pet peeve or two. That vs. Which, Who vs. Whom, terminal serial commas, singular they, sentence fragments, sentences beginning with a conjunction, split infinitives, sentences ending in a preposition–you may be driven into a fine froth when someone abuses your linguistic sensibilities.

That’s perfectly fine.

In a perfect world, lessons on Standard English would include both sides of each debate and examples of rule-breaking for stylistic effect, but there’s not enough room in the textbooks or time in the curriculum, so we learn “rules” that come to us as if written in stone.

We’re on our own to learn how to relax and accept the wide range of usage that’s appropriate to any given time or place. For me, after years of effort, I’m finally beginning to make some progress.

Three examples:

X Items or Less

For a long time, I used to bristle at the “12 items or less” supermarket checkout line. Didn’t anyone at that store remember that Strunk & White admonishes us all to never use “less” in place of “fewer?”


Some people have a copy of Strunk & White AND a Sharpie.

But even Strunk & White ignores the advice of Strunk & White, so why shouldn’t the rest of us? And when you think of it, the “less” in that sign doesn’t necessarily refer to the countable noun, “items.” It could also refer to an implied mass noun like “shopping,” as in the following hypothetical conversation:

“How much shopping are you going to do today?”

“Not much. I plan to buy twelve items, or maybe even do less shopping than that.”

“Then you should totally use the ’12 items or less [shopping]’ checkout line. It’s for people who are doing twelve items or less of shopping, so they can get out of the store faster.”

“Hey, thanks for the tip!”

The key difference is this:

“12 items or less” focuses on the shopping experience. People who are only grabbing a few urgently-needed items are looking to get in and out of the store quickly, and the checkout counters have been designed to move them ahead of shoppers who have set aside a larger block of time to stock up for the week.

“12 items or fewer” focuses on the items. Customers with fewer items to ring up can be processed faster, so they are grouped together and run through the checkout counter to minimize the total number of customers waiting at the front of the store.

I actually prefer the sentiment behind the first version, but since most people engaged in less shopping tend to purchase fewer items, the two versions are interchangeable in practice.

Say it with me, fellow recovering correcters of supermarket grammar: “The two versions are interchangeable.” No matter what Messrs. Strunk and White have to say about it.

I Could Care Less

I also used to go nuts over the words people used to place themselves at the bottom of the Caring Continuum. When someone told me, “Make all the nit-picky grammar and usage comments you want; I could care less,” they clearly intended to say that they couldn’t care less, while their words expressed the exact opposite sentiment.


I’d roll my eyes in wonder at people who were too ignorant or lazy to add a half-syllable “n’t” to make their expressions more accurate. However, I’ve since encountered evidence that “I could care less” started its idiomatic life as a devastating topper from the 1950s. Back then, people who didn’t care about things would brag that nobody could care less than they did.

The Setup: “Nobody could care less about that thing than I do.”

The Topper: “Oh yeah? Well I could care less. Mic-drop. You just got served!”

Or whatever the 1950s equivalent was.

Throughout the 1960s, people got tired of serving up the setup line, only to get slammed by the topper. So instead, they increasingly started with the topper. Over time people forgot that it even was a topper.

Today, what you’re really saying is implied:

“What do you think about Donald Trump?”

“I could care less [about Donald Trump than some other guy who claims that nobody could care less about Donald Trump than he does].”

Which makes perfectly acceptable grammatical, logical, and political sense.

Or think of it this way. When someone tells you they couldn’t care less about something, they have to be lying because they could always care enough less to not even bother speaking about that thing in the first place. Admitting that you could care less allows you to provide entertaining commentary about the infinitesimal amount of caring you do, as Randall Munroe presents in this episode of xkcd:

xkcd: I Could Care Less by Randall Munroe

Head over Heels

This one drove me particularly mad.

Being head-over-heels in love would seem to mean being in a completely ordinary and unremarkable position, since your head is nearly always over your heels whether you’re standing, sitting, or jumping up and down on Oprah’s couch.



The only time you’d not be “head over heels” would be when you’re horizontal–which is ironic in the context of a romantic relationship.

But here’s the actual first-known citation of “head over heels” in the English language, from Herbert Lawrence’s Contemplative Man in 1771:

“He gave [him] such a violent involuntary kick in the Face, as drove him Head over Heels.”

How could you drive someone head over heels if they weren’t head over heels already? And what does it mean that the method of driving someone head over heels is a particularly hard kick to the face?

I don’t have a copy of the source material, so I don’t know whether Contemplative Man is on the giving or receiving side of that history-making kick, but it works both ways:

Mayor: Contemplative Man, hurry! Captain Brainwave is robbing the bank!

Contemplative Man: Let me think about that. Hmmm…

Mayor: Now Captain Brainwave is robbing the art museum!

Contemplative Man: Hmmm…

Mayor: Now Captain Brainwave has kidnapped my daughter!

Contemplative Man: Hmmm…

Caption: Suddenly and without Warning, he gave him such a violent involuntary kick in the Face, as drove him Head over Heels!

Being “head over heels” probably wasn’t intended to mean that the character’s head was located just anywhere above his feet. Instead, due to a sudden blow, his neck was snapped back, his back was bent, and his legs were twisted so that head and feet, normally located at two opposite ends of the body, had come together with one resting directly on top of the other.

Take that, Captain Brainwave!

To be head-over-heels in love is to be twisted into a metaphorical pretzel, which expresses exactly how it can feel.


Love hurts.

I’m a lot happier (and more fun to be around) now that I’m no longer a rage-fueled grammatical pedant at the supermarket checkout, and no longer telling people how much they could or couldn’t care. And I’m a lot more flexible now that I can position my head and heels in a wider variety of ways.

I invite you to join me in my new pet peeve: people who inflexibly insist that their usage is the only correct way to communicate, instead of thinking creatively and accepting whatever language gets the point across.

Do you have any other pet peeves you’d like to be rid of? Leave them in the comments!

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Greg R. Fishbone
Greg R. Fishbone is the founder of Mythoversal, a project dedicated to restoring inclusion, diversity, and equity to classical texts, and Cryptoversal Books, a launchpad for experiments in sustainable Web3 publishing. His latest work is the Wordler Village series of innovative story tokens. Greg lives in New England with his wife, two young readers, and a pair of stubbornly illiterate cats.
  1. ‘Head ove heels’ describes a somersault position, a roll. It would be more logically phrased ‘heels over head over heels,’ but that is clearly a bit much.

  2. The use of irregardless in place of regardless.