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
For The Times) USC’s College World Series drought continues after a heartbreaking 4-3 walk-off loss to North Carolina in Game 3 of the Chapel Hill Super Regional.
—
Alan Cole, Los Angeles Times, 7 June 2026
Venezuela’s Gleiker Mendoza struck first at the 13-minute mark, giving fans of La Vinotinto reason to cheer after a heartbreaking exit from the South American World Cup qualifying campaign.
—Miami Herald, 7 June 2026
One of the most heartbreaking parts, from her daughter's perspective, is that none of those changes were necessary in the first place.
—Tereza Shkurtaj, PEOPLE, 7 June 2026
What was most memorable—or heartbreaking—about your stay?
—Condé Nast, Condé Nast Traveler, 4 June 2026
See All Example Sentences for heartbreaking
Alan Cole, Los Angeles Times, 7 June 2026
Venezuela’s Gleiker Mendoza struck first at the 13-minute mark, giving fans of La Vinotinto reason to cheer after a heartbreaking exit from the South American World Cup qualifying campaign.
—Miami Herald, 7 June 2026
One of the most heartbreaking parts, from her daughter's perspective, is that none of those changes were necessary in the first place.
—Tereza Shkurtaj, PEOPLE, 7 June 2026
What was most memorable—or heartbreaking—about your stay?
—Condé Nast, Condé Nast Traveler, 4 June 2026
See All Example Sentences for heartbreaking
Recent Examples of Synonyms for heartbreaking
Adjective
-
The sad thing for me is that, as a young actor, there was a platform for small independent films that were interesting.—
Rafa Sales Ross,
Variety,
11 June 2026
-
Someone said an ending can be both happy and sad at the same time, which is surely correct.—
Literary Hub,
Literary Hub,
10 June 2026
Adjective
-
Brexton Busch, the 11-year-old son of NASCAR superstar Kyle Busch, did something for the first time since the sudden and tragic passing of his father.—
Alex Zietlow,
Charlotte Observer,
11 June 2026
-
In his hands, Tom can be buffoonish, tragic, doomed and heroic at once.—
David Canfield,
HollywoodReporter,
11 June 2026
Adjective
-
Sports make people a little pathetic.—
Hannah Keyser,
CNN Money,
9 June 2026
-
Williams didn't portray Peter Banning as pathetic.—
Cynthia Pelayo,
PEOPLE,
8 June 2026
Adjective
-
After watching and enjoying the film, a somewhat depressing thought leaped into my mind.—
Angelica Jade Bastién,
Vulture,
8 June 2026
-
After a depressing four-year hiatus, Bus Palladium has been transformed into a 35-room luxury hotel with a bar, restaurant, and club by building owner Christian Casmèze and hotelier Nicolas Saltiel, with architecture and interiors by the design firm Studio KO.—
Alexander Lobrano,
Air Mail,
6 June 2026
Adjective
-
There’s no question that this unfortunate cocktail of corruption, inefficiency, and simple incompetence is holding the country back.—
Daniel Alarcón,
New Yorker,
4 June 2026
-
Unfortunately, going cold turkey off a central nervous system depressant like GHB has some pretty unfortunate side-effects.—
Bethy Squires,
Vulture,
3 June 2026
Adjective
-
Trump has made a pitiful shambles of what should have been a glorious moment.—
David Frum,
The Atlantic,
31 May 2026
-
With his country flailing in their pitiful attempts to qualify for the 2006 World Cup, at the age of 33, Zidane underwent his change of heart.—
Amy Lawrence,
New York Times,
31 May 2026
Adjective
-
The second didn’t go nearly as well for Bussi as Karlsson and Howden scored on two of the Golden Knights’ six shots in the period to tie the score at 3-3 heading into the third, the tying goal coming off a Seth Jarvis turnover and a couple of poor defensive plays by Sean Walker and K’Andre Miller.—
Michael Russo,
New York Times,
10 June 2026
-
Heat radiates from the pages of this extraordinary novel about a poor family in rural Mississippi in the days leading up to Hurricane Katrina.—
Literary Hub,
Literary Hub,
9 June 2026
Adjective
-
The sea was rough, windy, and miserable.—
Robert McGreevy,
FOXNews.com,
6 June 2026
-
The Angels thumped the Colorado Rockies 11-4, but one good night cannot change the trajectory of a miserable season.—
Bill Shaikin,
Los Angeles Times,
4 June 2026
Cite this Entry
“Heartbreaking.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/heartbreaking. Accessed 14 Jun. 2026.
Copy CitationLove words? Need even more definitions?
Merriam-Webster unabridged
