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
Gertie’s broken tail was a desperate and heartbreaking sign of her relief and gratitude, the news release stated.
—
News Release, San Diego Union-Tribune, 27 Mar. 2026
Sometimes darkly humorous, sometimes strangely heartbreaking, this immersive storytelling experience is Edgar Allan Poe for the modern age; a heart-to-bleeding-heart with madmen, murderers and monsters all dying to tell their story.
—William Earl, Variety, 25 Mar. 2026
Last season’s collapse was as maddening as the 15-inning game was heartbreaking.
—Cody Stavenhagen, New York Times, 25 Mar. 2026
The team has a ton of momentum, but so did last year’s squad — the 2025 season came to a sudden end with a heartbreaking 1-0 loss to Wolfforth Frenship in the area round.
—Charles Baggarly, Fort Worth Star-Telegram, 23 Mar. 2026
See All Example Sentences for heartbreaking
News Release, San Diego Union-Tribune, 27 Mar. 2026
Sometimes darkly humorous, sometimes strangely heartbreaking, this immersive storytelling experience is Edgar Allan Poe for the modern age; a heart-to-bleeding-heart with madmen, murderers and monsters all dying to tell their story.
—William Earl, Variety, 25 Mar. 2026
Last season’s collapse was as maddening as the 15-inning game was heartbreaking.
—Cody Stavenhagen, New York Times, 25 Mar. 2026
The team has a ton of momentum, but so did last year’s squad — the 2025 season came to a sudden end with a heartbreaking 1-0 loss to Wolfforth Frenship in the area round.
—Charles Baggarly, Fort Worth Star-Telegram, 23 Mar. 2026
See All Example Sentences for heartbreaking
Recent Examples of Synonyms for heartbreaking
Adjective
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One of the saddest bits of it, actually!—
Maggie Fremont,
Vulture,
26 Mar. 2026
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Sister Jean would pass away at age 106 this past October, a sad metaphor for the fate of Cinderella.—
Greg Cote
Updated March 23,
Miami Herald,
23 Mar. 2026
Adjective
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OpenAI is battling more than a dozen different death and harm suits, including one centered on a tragic murder-suicide allegedly spurred by ChatGPT reinforcing an unstable man’s paranoid delusions.—
Maggie Harrison Dupré,
Futurism,
26 Mar. 2026
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The major hubs are bad in all the predictable ways, but America’s smaller airports are each cursed and tragic in their own exquisite style.—
Ellen Cushing,
The Atlantic,
26 Mar. 2026
Adjective
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The politicians who shut down the government are pathetic on both sides of the aisle.—
Joe Soucheray,
Twin Cities,
28 Mar. 2026
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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
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All airports are depressing and scary; some go above and beyond.—
Ellen Cushing,
The Atlantic,
26 Mar. 2026
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And people in Silicon Valley are after efficiency, which lacks humanity and can be horribly depressing.—
Marta Balaga,
Variety,
21 Mar. 2026
Adjective
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That house has a history of unfortunate events, including the fate of Cookie, an errant heiress and her pooch.—
Pat Beall,
Sun Sentinel,
27 Mar. 2026
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The start of 2026 has been a series of unfortunate events for Michelle Harris and her family.—
Monique John,
CBS News,
27 Mar. 2026
Adjective
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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
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The rear cargo space is pitiful for a vehicle of this size, price, and classification.—
Jesus R. Garcia,
Houston Chronicle,
15 Mar. 2026
Adjective
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Serious Medical and Emotional Neglect Turner said Kaiko arrived in poor health, suffering from multiple medical issues and signs of prolonged neglect.—
Alice Gibbs,
MSNBC Newsweek,
31 Mar. 2026
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The city of Plano scores restaurants on a 100-point system, with 100 considered a perfect score and 70 extremely poor.—
Fort Worth Star-Telegram,
Fort Worth Star-Telegram,
31 Mar. 2026
Adjective
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Or a miserable 48 in the case of the Rangers, still simmering in Philadelphia.—
Kevin Sherrington
Mar. 27,
Dallas Morning News,
27 Mar. 2026
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Their home is huge and elegant, but also maze-like, miserable, and allergic to light.—
Ben Travers,
IndieWire,
26 Mar. 2026
Cite this Entry
“Heartbreaking.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/heartbreaking. Accessed 3 Apr. 2026.
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