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
The 2022-23 Bruins had shattered records with a 65-win season, only to blow a 3-1 series lead in the first round and lose to the Panthers in seven heartbreaking games.
—
Sean McIndoe, New York Times, 8 Oct. 2025
Sims revealed the heartbreaking news in a post on Instagram.
—Ryan Gaydos, FOXNews.com, 6 Oct. 2025
As a freshman, Toney faced one of the toughest situations of his football life when a costly fumble in the closing seconds of the state championship game against Miami Central resulted in a heartbreaking defeat.
—Andre Fernandez, Miami Herald, 5 Oct. 2025
What’s happening to children in Gaza is heartbreaking.
—Jack Dunn, Variety, 5 Oct. 2025
See All Example Sentences for heartbreaking
Sean McIndoe, New York Times, 8 Oct. 2025
Sims revealed the heartbreaking news in a post on Instagram.
—Ryan Gaydos, FOXNews.com, 6 Oct. 2025
As a freshman, Toney faced one of the toughest situations of his football life when a costly fumble in the closing seconds of the state championship game against Miami Central resulted in a heartbreaking defeat.
—Andre Fernandez, Miami Herald, 5 Oct. 2025
What’s happening to children in Gaza is heartbreaking.
—Jack Dunn, Variety, 5 Oct. 2025
See All Example Sentences for heartbreaking
Recent Examples of Synonyms for heartbreaking
Adjective
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One purveyor of fairy tales that wasn’t afraid of a sad ending?—
Elisabeth Sherman,
Parents,
3 Oct. 2025
-
Sade Bess, a Combs fan from Brooklyn, left the court’s overflow observation room looking both sad and relieved.—
Jennifer Peltz,
Fortune,
3 Oct. 2025
Adjective
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This film largely focuses on Desai’s story – including a tragic twist at the end of his life.—
Catherine E. Shoichet,
CNN Money,
4 Oct. 2025
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She's also found ways for students to help in tragic circumstances before.—
John Wisely,
Freep.com,
3 Oct. 2025
Adjective
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Characters can be pathetic, and frank about their Toledo Truth Teller’s bleak prospects.—
Brittany Allen,
Literary Hub,
23 Sep. 2025
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Jimmy Kimmel is a pathetic hate monger.—
Dave Smith,
Fortune,
18 Sep. 2025
Adjective
-
Coordinating your exhales with the pressing, depressing, pulling and lifting phases of these exercises enhances activation of the scapular stabilizing muscles and reinforces proper rib cage alignment.—
Dana Santas,
CNN Money,
2 Oct. 2025
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Closing The Gap The racial wealth gap in America remains depressing, and homeownership is one of the clearest indicators of it.—
Essence,
Essence,
1 Oct. 2025
Adjective
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To lose Livramento and Hall at the same time is unfortunate and has left Newcastle stretched down the defensive flanks, but letting Targett go was the right decision.—
Chris Waugh,
New York Times,
7 Oct. 2025
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The track record in Jacksonville is a series of unfortunate events, and that hasn’t been because of the record.—
Kansas City Star,
Kansas City Star,
7 Oct. 2025
Adjective
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The Browns have scored the second-fewest points in the NFL, ahead of only the pitiful Tennessee Titans.—
Jason Lloyd,
New York Times,
28 Sep. 2025
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On the side of the highway, Wilson cuts a pitiful, solitary figure.—
Dan Piepenbring,
Harpers Magazine,
19 Sep. 2025
Adjective
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My adolescent cells floated away from poor me and traded places with his.—
Betty Gilpin,
HollywoodReporter,
9 Oct. 2025
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Women disproportionately suffer chronic disease, on average spend 25% more time in poor health than men, and, on average, experience the final 12 to 14 years of their lives in frail health.—
Maria Shriver,
Time,
9 Oct. 2025
Adjective
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The upshot of this contempt is a season that layers hypocrisy as well as sanctimony over the grubby, tedious nihilism that made Dahmer so miserable to watch.—
Judy Berman,
Time,
6 Oct. 2025
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In the end, Jawan took pity on the miserable lot over on Kele and put the disadvantage of having to carry 20 pounds of coconuts and cycle through 10 keys instead of just one on Hina instead, saying Kele had been through too much already.—
Dalton Ross,
Entertainment Weekly,
2 Oct. 2025
Cite this Entry
“Heartbreaking.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/heartbreaking. Accessed 10 Oct. 2025.
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