The Saddest Phrases In The English Language

back to school

If fall is approaching, that means we’ve grappled with three of the saddest words in the English language: back to school. Most kids loathe this phrase. (It may also belong on our Happiest Words list, with regard to a different demographic.)

While there’s no hard data to support that this is one of the saddest phrases in the English language, we think polling a group of kids on how the words make them feel would yield some pretty sad looks and plenty of complaints.

Interestingly, the phrase back to school became popular during World War I, when back-to-school drive referred to a movement encouraging children and teens to return to school after filling jobs during the labor shortage. (How’s that for somber?)

What other phrases cause distress, despair, and discomfort? Grab a hankie or two and check out this list of some of the saddest words and phrases we could find.

WATCH: We Asked These People To Explain The Saddest English Phrases


Heartbroken is a tough word. We define it as “crushed with sorrow or grief.” We’ve all been there at one time or another—you know it as soon as you feel it, and you can’t wait for it to go away. This concept tends to rear its ugly head around February 14.

First recorded around 1580–90, heartbroken combines heart and broken. Here’s how someone used the phrase early on: “He hath annointed me … to heale them that be hart broken.” (Oh, how tragic!)


An astute poster on Quora once wrote, “you say [goodbye] all the time, but you never know which one is the last.” It’s pretty safe to assume you know why this word made it on our list. As we learned in Romeo and Juliet, “Parting is such sweet sorrow.”

The practice of saying goodbye goes back centuries, with first evidence of the interjection found around 1565–75. It’s a contraction of the phrase “God be with ye.”


Learn more about this wistful term of farewell at our article, “The Holy Reason We Say ‘Goodbye’ And What To Say Instead.”

if only

If only can be defined as “I wish that.” For example: If only I had known you were coming, I would have met your plane. This expression can also be one of wistful regret, as in If only we had met 10 years ago. Both if and only are old words, dating back to before 900.


If you’re lonely, you are inherently sad. One (er, sadly) goes with the other. Lonely (which combines lone and -ly) was first recorded in English around 1600. Lone itself dates back to around 1325–75; it’s a variant of alone.

There’s no possible way to put a positive spin on this one. So, we’ll just leave it be.


The word love is evocative of a (mostly) positive and fulfilling emotion, and even has its own holiday every February.

There is a flip side to the coin, however. If love is unrequited, it’s the worst, and that’s why it’s on this list. The word dates back to 1535–45. Requite means “to give or do in return.”


We define melancholy as “a gloomy state of mind, especially when habitual or prolonged; depression.” As an example, think about Charlie Brown lying on the pitching mound after getting drilled with yet another line drive.

Brace yourself: the word melancholy has a dark, heartbreaking origin. First recorded in 1275–1325, it is derived from the Greek melancholía, which means “condition of having black bile” (from melan- meaning “black,” cholḗ meaning “bile, gall,” and the suffix ia.) Bile is a “bitter, alkaline, yellow or greenish liquid, secreted by the liver.” (That’s definitely a downer.)


Terminal is never a good word when used in a medical context. It is another word to which it is nearly impossible to put a good spin. Terminal dates back to around 1480 and is ultimately derived from the Latin word terminus (“end, limit”).

What party?

How about a little joke to lighten the mood? The late Carrie Fisher said two of the saddest words in the English language were “what party?” The one you weren’t invited to, it would seem.

time for bed

Just like our earlier phrase back to school, this one will resonate with the elementary-school scene. Homework’s done, and you’ve got a little latitude to stay up and watch TV. Around 8:40pm or so, though, you start doing a little clock watching. Tick tock. Then, right at the 8:51pm commercial break come those ominous words from the kitchen. “Honey, almost time for bed … ” The word time comes from the Old English tima (“limited space of time”).


Trick your parents into delaying that bedtime by jumping into a discussion over the difference between sometime, sometimes, and some time.

no time

Speaking of time, what happens when you’ve run out of time? But time for what? To clean the house, to call your parents, to repair your relationship. No time is an easy out, a mindless way of defending no action. Want to turn your sad words into happy ones? There’s time.


An interesting choice, no? We’re not talking Mulder and Scully aliens, though. If someone is referred to as an alien, it means they are a foreigner … and, the implication is that they don’t belong. Since everyone wants to feel like they fit in wherever they might be, the label of alien can be a hard cross to bear. That’s why the word is considered disparaging and offensive.

Alien was first recorded in 1300–50 and is ultimately derived from the Latin aliēnus (“of or belonging to others”).


This word is tinged with perpetual runner-up status. Almost is defined as “very nearly, all but.” She almost won the race. He almost scored an A on the test. They almost won the lottery. Alas, if almost is firmly lodged in your vocabulary, you may continuously be one step behind everyone else. There’s always next time, right? Before the year 1000, you would have used the older version of this word: eal māst.


There is just nothing good to say about forlorn. (We’re getting depressed just typing this.) “Desolate or dreary; unhappy or miserable … ” The meaning draws a pretty bleak picture. You’re blue, down in the dumps, woebegone. That’s a forlorn feeling, for sure. This word is recorded in English before 1150. It stems from the Middle English forlesen (“to lose completely”).

bad news

“I’ve got some bad news … ” That’s a phrase—originating in the 1910s—that is always followed by sadness. “Bad news” can range from a variety of information, but regardless of the severity, the news that is given isn’t going to make your day. If you hear this phrase uttered in your direction, get ready to navigate the upcoming dire straits.

too late

This phrase is generally colored with the brush of regret. “You’re too late, you missed the deadline.” “He was too late, she went with someone else.” “It was too late for an apology.” Or, even worse, “We were too late to stop him.” Whatever the reason, too late means you are missing out on the fun, so pick up the speed!

Late was first recorded in English before 900. It’s related to the German lass (“slothful”), the Gothic lats (“slow, lazy”), and the Latin lassus (“tired”).

no more ice cream

In the 1680s, it was known as iced cream. Today, it’s ice cream, of course. Either way, if you’ve pried open the lid to the gallon of sitting in your freezer only to find an empty carton staring back, this phrase is one of the worst.

Especially when you’re raiding the fridge at 3 am …

Need a pick-me-up?

Are you feeling pretty down and out after that list? Need a pick-me-up? Check out our list of Verbal Pick-me-ups That Will Brighten Your Day to turn that frown upside down.


Look beyond your sadness for a moment and realize there are more eloquent ways to describe that forlorn feeling and more. Read about some in this list of words that go beyond sad, glad, and mad.

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