1
as in sad
causing unhappiness
a heartbreaking story of a family torn asunder by war
Synonyms & Similar Words
Relevance
Antonyms & Near Antonyms
2
as in tragic
of a kind to cause great distress
the heartbreaking state of Main Street now that most of the businesses have closed
Synonyms & Similar Words
Antonyms & Near Antonyms
3
as in pathetic
deserving of one's pity
a heartbreaking attempt to escape that ends in disaster
Synonyms & Similar Words
Antonyms & Near Antonyms
Example Sentences
Examples are automatically compiled from online sources to
show current usage.
Read More
Opinions expressed in the examples do not represent those of Merriam-Webster or its editors.
Send us feedback.
Recent Examples of heartbreaking
And just days after Moriah’s birth, on May 18, 1996, Wilson was hit with the heartbreaking notion that Moriah would leave her someday.
—
Erin Jensen, USA Today, 3 Apr. 2026
Part of that journey is reading books about grief to help the parents navigate the heartbreaking process of preparing their daughters face an uncertain future.
—Cara Lynn Shultz, PEOPLE, 31 Mar. 2026
What was most memorable—or heartbreaking—about your stay?
—Condé Nast, Condé Nast Traveler, 31 Mar. 2026
The Duke Blue Devils’ season ended in about as heartbreaking fashion as one could’ve imagined.
—Michael Gallagher, MSNBC Newsweek, 30 Mar. 2026
See All Example Sentences for heartbreaking
Erin Jensen, USA Today, 3 Apr. 2026
Part of that journey is reading books about grief to help the parents navigate the heartbreaking process of preparing their daughters face an uncertain future.
—Cara Lynn Shultz, PEOPLE, 31 Mar. 2026
What was most memorable—or heartbreaking—about your stay?
—Condé Nast, Condé Nast Traveler, 31 Mar. 2026
The Duke Blue Devils’ season ended in about as heartbreaking fashion as one could’ve imagined.
—Michael Gallagher, MSNBC Newsweek, 30 Mar. 2026
See All Example Sentences for heartbreaking
Recent Examples of Synonyms for heartbreaking
Adjective
-
And there is a beautiful human element to it that is kind of, at its core, a little sad.—
Rebecca Alter,
Vulture,
9 Apr. 2026
-
The vlogger Jordan Cheyenne, for one, wrecked her sharenting career by accidentally posting footage of herself coaching her son, who was distraught over the family’s sick puppy, to make a specific kind of sad face for YouTube.—
Jessica Winter,
New Yorker,
7 Apr. 2026
Adjective
-
Lying in this crypt is Nathan Lane’s Willy Loman, a tragic humbug, his delusions contradicted by the ruins around him.—
Hilton Als,
New Yorker,
10 Apr. 2026
-
These are films that reflect the human condition through inspirational tales of struggle, tragic true stories, life-threatening conflicts, and intimate psychological portraits.—
Kevin Jacobsen,
Entertainment Weekly,
9 Apr. 2026
Adjective
-
The politicians who shut down the government are pathetic on both sides of the aisle.—
Joe Soucheray,
Twin Cities,
28 Mar. 2026
-
His Floyd constantly straddles the line between sweet and pathetic, often falling off one side or the other.—
Bill Goodykoontz,
AZCentral.com,
24 Mar. 2026
Adjective
-
Sam Levinson’s vision of a woman’s life is pretty depressing.—
Savannah Salazar,
Vulture,
10 Apr. 2026
-
In his teaching, Weil conveyed his love for Russian literature’s very lengthy — and at times dark and depressing — novels with enthusiasm and aplomb, colleagues recalled.—
Bob Goldsborough,
Chicago Tribune,
7 Apr. 2026
Adjective
-
The Russian ambassador to Libya hung out in my room, as did a Russian kid named Konstantin with an unfortunate stutter and endearing affection for the American rock band Metallica.—
Literary Hub,
Literary Hub,
3 Apr. 2026
-
The film is a Hulu release, continuing the rather unfortunate trend of comedy no longer being the box office powerhouse it once was.—
Brian Davids,
HollywoodReporter,
3 Apr. 2026
Adjective
-
Given that California ranks a pitiful 49th in the nation in the condition, safety and costs of roads and bridges, according to the Reason Foundation’s 2025 Annual Highway Report, taxpayers’ transportation dollars would likely be better spent elsewhere.—
Adam Summers,
San Diego Union-Tribune,
20 Mar. 2026
-
The rear cargo space is pitiful for a vehicle of this size, price, and classification.—
Jesus R. Garcia,
Houston Chronicle,
15 Mar. 2026
Adjective
-
Arsenal were pretty poor but won, Sporting were pretty good but lost.—
Tim Spiers,
New York Times,
8 Apr. 2026
-
Ackman blamed its poor share price performance partly on the delay of UMG’s listing in the United States.—
Zac Ntim,
Deadline,
7 Apr. 2026
Adjective
-
Wagler led the Illini with 20 points, but Illinois shot a miserable 34% (19 of 56) from the field and 23% (6 of 26) from 3-point range.—
Paul Sullivan,
Chicago Tribune,
5 Apr. 2026
-
Porter Martone capped a fantastic first week in the NHL with a power-play goal in the NHL to put the Philadelphia Flyers even closer toward ending a miserable playoff drought with a 2-1 overtime victory over the Boston Bruins on Sunday.—
CBS News,
CBS News,
5 Apr. 2026
Cite this Entry
“Heartbreaking.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/heartbreaking. Accessed 12 Apr. 2026.
Copy CitationLove words? Need even more definitions?
Merriam-Webster unabridged
