1
as in sad
causing unhappiness
a heartbreaking story of a family torn asunder by war
Synonyms & Similar Words
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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
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Antonyms & Near Antonyms
Example Sentences
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Recent Examples of heartbreaking
Like the friendships at its core, The Four Seasons is funny, flawed, and occasionally heartbreaking.
—
Dana Feldman, Forbes.com, 30 May 2026
Perhaps the most heartbreaking was Damon Hill’s 1997 Hungarian race.
—Jonathan M. Gitlin, ArsTechnica, 29 May 2026
The commissioners have also overseen the heartbreaking and mounting losses of species such as Florida gopher tortoises to development.
—Joe Murphy, The Orlando Sentinel, 28 May 2026
In a year that was full of heartbreaking celebrity deaths, the unlikely death of a gorilla rocked 2016.
—Angela Andaloro, PEOPLE, 28 May 2026
See All Example Sentences for heartbreaking
Dana Feldman, Forbes.com, 30 May 2026
Perhaps the most heartbreaking was Damon Hill’s 1997 Hungarian race.
—Jonathan M. Gitlin, ArsTechnica, 29 May 2026
The commissioners have also overseen the heartbreaking and mounting losses of species such as Florida gopher tortoises to development.
—Joe Murphy, The Orlando Sentinel, 28 May 2026
In a year that was full of heartbreaking celebrity deaths, the unlikely death of a gorilla rocked 2016.
—Angela Andaloro, PEOPLE, 28 May 2026
See All Example Sentences for heartbreaking
Recent Examples of Synonyms for heartbreaking
Adjective
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The other six ascended to the highest office in the land as a result of the dysfunction that has made Peru a punch line in political-science circles, a sad story of ungovernability played on a loop.—
Daniel Alarcón,
New Yorker,
4 June 2026
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There’s a one-note quality to the film’s comedy that grows steadily, even deliberately, more abrasive over two hours, but the sad, brash, gradually shrinking bigness of the personalities at its center holds your attention.—
Guy Lodge,
Variety,
4 June 2026
Adjective
-
Emergency responders say the toddler's death is a tragic reminder of how dangerous the water is, especially at this time of year when peak water flows are being recorded.—
Dillon Thomas,
CBS News,
4 June 2026
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During closing arguments on Monday, an attorney for the family of the two boys called on the jury to assess hundreds of millions of dollars in damages, rejecting the defense contention that what occurred was a tragic accident.—
City News Service,
Daily News,
3 June 2026
Adjective
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By then, Thomsen says, the public perception had shifted from regarding it as tough and controversial to seeing it as desperate and pathetic.—
Harmeet Kaur,
CNN Money,
28 May 2026
-
The plan involved discovering a long lost princess, hopping on a plane to London, breaking into a museum store room, and enlisting the help of a very pathetic historian.—
Shania Russell,
Entertainment Weekly,
22 May 2026
Adjective
-
Almost a year out to sea is very depressing.—
Steve Walsh,
NPR,
23 May 2026
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Some sendoffs are mundane; others are downright depressing.—
Michael Silver,
New York Times,
21 May 2026
Adjective
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The timing is particularly unfortunate given the matchup awaiting the Knicks.—
Kristian Winfield,
New York Daily News,
29 May 2026
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While loud sounds won’t cause flat cakes, there are reasons for this unfortunate outcome.—
BestReviews,
Chicago Tribune,
29 May 2026
Adjective
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Chilling moments like this are the lifeblood of The Dreamed Adventure, the moments that recall the pitiful last days of the dying communist era and the violent, mafia-style economics that whooshed in to replace them.—
Damon Wise,
Deadline,
22 May 2026
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There’s a mentality problem — that’s highlighted by a pitiful return of just one point out of a possible 24 away from home this season against teams in the top nine.—
James Pearce,
New York Times,
16 May 2026
Adjective
-
Common travel regrets stem from preventable issues like poor planning, budget problems, and choosing the wrong companions.—
Kathleen Wong,
USA Today,
3 June 2026
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O’Farrell’s inclination for narratives propelled by brutal coincidence and fatally poor timing tenders a Hardy-esque vision of the world, one that emphasizes the rigid, often cruel limits of an individual’s jurisdiction over the course of their life.—
Rachel Vorona Cote,
Vulture,
2 June 2026
Adjective
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The $50 million playland opened in miserable Memorial Day weekend weather, but 12,000 visitors still showed up.—
Kori Rumore,
Chicago Tribune,
29 May 2026
-
Let’s survey the wreckage of another miserable day at the ballpark.—
Dieter Kurtenbach,
Mercury News,
27 May 2026
Cite this Entry
“Heartbreaking.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/heartbreaking. Accessed 6 Jun. 2026.
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