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
Synonyms & Similar Words
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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There were enough people in the room who were sad about the kid.—
Ben Rosenstock,
Vulture,
2 Apr. 2026
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And that’s really sad, because the latest gen is a genuinely fantastic car.—
Adam Ismail,
The Drive,
2 Apr. 2026
Adjective
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Another effort will be going into local schools to make sure students understand that a simple mistake can be the start of something tragic for everyone in the mountain communities.—
Spencer Wilson,
CBS News,
3 Apr. 2026
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When a series of tragic failures at New Era Community Health Center left scores of the county’s weakest, poorest and most erratic residents in danger, Florida health inspectors took the unusual step of threatening to shut down the home.—
Carol Marbin Miller,
Miami Herald,
2 Apr. 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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The Knicks went on to defeat the tanking, depleted Grizzlies handily, a 130-119 win good enough to snap a depressing three-game losing streak against the Charlotte Hornets, Houston Rockets and Oklahoma City Thunder.—
Kristian Winfield,
New York Daily News,
2 Apr. 2026
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Far from a depressing gray room located in a basement, The Bridge and its massive windows put a spotlight on the natural beauty of Hong Kong.—
Matt Ortile,
Condé Nast Traveler,
31 Mar. 2026
Adjective
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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
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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
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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 6 Apr. 2026.
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