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 victory, three years after a heartbreaking second-place finish at the tournament, placed McIlroy in rare company, as the sixth golfer to complete the modern-era Grand Slam with a victory at all four major tournaments, after Gene Sarazen, Ben Hogan, Gary Player, Jack Nicklaus and Tiger Woods.
—
Justin Birnbaum, Forbes.com, 11 June 2025
In fact, the song is presented from the point of view of someone who may well be dealing with unrequited love, which is of course the most heartbreaking kind of all.
—Marco Della Cava, USA Today, 11 June 2025
To achieve this heartbreaking moment, Barantini and Hannah Walters, surrounded by her and Graham’s children Grace and Alfie, surprised Graham.
—Peter White, Deadline, 11 June 2025
Israel’s Hostages and Missing Families Forum welcomed the latest news, calling it both heartbreaking and healing.
—Eugenia Yosef, CNN Money, 5 June 2025
See All Example Sentences for heartbreaking
Justin Birnbaum, Forbes.com, 11 June 2025
In fact, the song is presented from the point of view of someone who may well be dealing with unrequited love, which is of course the most heartbreaking kind of all.
—Marco Della Cava, USA Today, 11 June 2025
To achieve this heartbreaking moment, Barantini and Hannah Walters, surrounded by her and Graham’s children Grace and Alfie, surprised Graham.
—Peter White, Deadline, 11 June 2025
Israel’s Hostages and Missing Families Forum welcomed the latest news, calling it both heartbreaking and healing.
—Eugenia Yosef, CNN Money, 5 June 2025
See All Example Sentences for heartbreaking
Recent Examples of Synonyms for heartbreaking
Adjective
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The building directly across the street stands in sad disrepair, its windows smashed, swathed in graffiti, a front garage door hangs half-open.—
Eric Adler,
Kansas City Star,
19 June 2025
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Two screenshots from the video showing Ollie was a sad facial expression.—
Lucy Notarantonio,
MSNBC Newsweek,
19 June 2025
Adjective
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The freaky period piece and tragic family drama features Anja Taylor-Joy as a troubled 17th-century teen on the cusp of adulthood who goes down a dark path and Black Phillip as the G.O.A.T. of hellish goats. 23.—
Brian Truitt,
USA Today,
14 June 2025
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This is not just the story of that tragic moment and that heinous crime.—
Samantha Balaban,
NPR,
14 June 2025
Adjective
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So why did a chess engine that came under the pathetic category and only looks one move ahead not just defeat but humiliate ChatGPT?—
David Szondy
June 15,
New Atlas,
15 June 2025
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Not because ownership has had a change of heart, but rather as a way to address their pathetic offense.—
Mac Engel,
Fort Worth Star-Telegram,
6 June 2025
Adjective
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And books about cancer don’t have to be depressing.—
Terry McDonell
June 11,
Literary Hub,
11 June 2025
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That was a bit depressing, that first paintbrush touching your skin.—
Daniel D'Addario,
Variety,
2 June 2025
Adjective
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Shakira does appear to be the beneficiary of an unintended consequence stemming from her unfortunate moves.—
Hugh McIntyre,
Forbes.com,
21 June 2025
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The unfortunate widowed Ellen Brody (Lorraine Gary) heads down to the Bahamas to visit her son, Michael (Lance Guest), and guess who follows?—
Chris Nashawaty,
EW.com,
20 June 2025
Adjective
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For better or worse, high-end eco-resorts of this type tend to focus on hyper-local ingredients often grown in a pitiful little garden behind the kitchen.—
Christopher Cameron,
Robb Report,
30 May 2025
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From ’01 to ’20, the Knicks played in only 30 postseason games, posting a pitiful 9-21 record.—
Rohan Nadkarni,
NBC news,
18 May 2025
Adjective
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Orlik, who was seventy-seven, was in poor health and desperate to get his pictures back.—
Sam Knight,
New Yorker,
17 June 2025
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In past decades, this stage was easy to spot: clashing colors, poor makeup attempts, and wardrobes inspired by favorite TV stars.—
Dia Gallo,
Parents,
17 June 2025
Adjective
-
Championship-only fandom is a largely miserable existence.—
Ira Winderman,
Sun Sentinel,
19 June 2025
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Unexpectedly miserable league seasons last time around for Tottenham and Manchester United — the final opponents at the Amex Stadium next May — are another reason why forecasting is hazardous, especially in Brighton’s case.—
Andy Naylor,
New York Times,
18 June 2025
Cite this Entry
“Heartbreaking.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/heartbreaking. Accessed 25 Jun. 2025.
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