heartbreaking
adjective
heart·break·ing ˈhärt-ˌbrā-kiŋ 
1
: causing intense sorrow or distress
heartbreaking news
a heartbreaking defeat
2
: producing an intense emotional reaction or response
heartbreaking beauty
heartbreakingly
ˈhärt-ˌbrā-kiŋ-lē
adverb a heartbreakingly tragic movie
Synonyms
- depressing
- dismal
- drear
- dreary
- heartrending
- melancholy
- mournful
- pathetic
- sad
- saddening
- sorry
- tearful
- teary
See all Synonyms & Antonyms 
Example Sentences
She wrote a heartbreaking story about the death of her grandfather. It was heartbreaking to know that there was nothing I could do. The team suffered another heartbreaking defeat.
Recent Examples on the Web Daughter Natalia also shared a beautiful and heartbreaking picture of herself and her father sitting courtside at what appeared to be a basketball game. 
Alexandra Schonfeld, Peoplemag, 23 Aug. 2022 Kertzer’s depiction of Vatican politics during the war is even more heartbreaking. John Loughery, Washington Post, 29 July 2022 The history of hate crimes against Asian Americans is long and heartbreaking. Amy Dickinson, Chicago Tribune, 10 July 2022 The history of hate crimes against Asian Americans is long and heartbreaking. cleveland, 10 July 2022 The history of hate crimes against Asian Americans is long and heartbreaking. Amy Dickinson, oregonlive, 10 July 2022 Episode 9 is bigger and badder, and to my mind, even more heartbreaking than this one. Dan Snierson, EW.com, 12 July 2022 At times both hilarious and heartbreaking, viewers might be shocked at this look inside a British institution. Amy Mackelden, ELLE, 30 June 2022 The anticipation of a breakup is probably more heartbreaking than the actual split: even more so when one partner realizes it’s over before the other. Richy Rosario, Billboard, 27 June 2022 See More
Alexandra Schonfeld, Peoplemag, 23 Aug. 2022 Kertzer’s depiction of Vatican politics during the war is even more heartbreaking. John Loughery, Washington Post, 29 July 2022 The history of hate crimes against Asian Americans is long and heartbreaking. Amy Dickinson, Chicago Tribune, 10 July 2022 The history of hate crimes against Asian Americans is long and heartbreaking. cleveland, 10 July 2022 The history of hate crimes against Asian Americans is long and heartbreaking. Amy Dickinson, oregonlive, 10 July 2022 Episode 9 is bigger and badder, and to my mind, even more heartbreaking than this one. Dan Snierson, EW.com, 12 July 2022 At times both hilarious and heartbreaking, viewers might be shocked at this look inside a British institution. Amy Mackelden, ELLE, 30 June 2022 The anticipation of a breakup is probably more heartbreaking than the actual split: even more so when one partner realizes it’s over before the other. Richy Rosario, Billboard, 27 June 2022 See More Word History
First Known Use
1591, in the meaning defined at sense 1a
Kids Definition
heartbreaking
adjective
heart·break·ing ˈhärt-ˌbrā-kiŋ
: causing great sorrow a heartbreaking story
heartbreaking
adjective
1
as in sad
causing unhappiness a heartbreaking story of a family torn asunder by war Synonyms & Similar Words
Relevance
- sad
- depressing
- pathetic
- saddening
- tearful
- mournful
- unfortunate
- disturbing
- melancholy
- heartrending
- teary
- dismal
- poignant
- sorry
- dreary
- drear
- distressful
- distressing
- lamentable
- deplorable
- touching
- disquieting
- disheartening
- discomforting
- discouraging
- affecting
- moving
- grievous
- dispiriting
- woeful
- perturbing
- discomposing
Antonyms & Near Antonyms
- happy
- glad
- inspiring
- cheery
- uplifting
- heartening
- delightful
- stirring
- stimulating
- pleasant
- heartwarming
- enjoyable
- satisfying
- cheering
- pleasurable
- welcome
- thrilling
- exhilarating
- pleasing
- agreeable
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
- tragic
- unfortunate
- tragical
- shocking
- terrible
- heartrending
- distressing
- painful
- disturbing
- horrible
- sad
- regrettable
- deplorable
- distressful
- lamentable
- unsettling
- sickening
- poignant
- grievous
- woeful
- awful
- horrifying
- unlucky
- dire
- disastrous
- dreadful
- harrowing
- traumatic
- unbearable
- pitiful
- touching
- miserable
- affecting
- alarming
- troublesome
- fearful
- moving
- doleful
- excruciating
- overwhelming
- severe
- piteous
- crushing
- vexatious
- wretched
- perturbing
- intolerable
- calamitous
- ruthful
- raging
- sharp
Antonyms & Near Antonyms
- rewarding
- gratifying
- satisfying
- pleasing
- comforting
- heartening
- encouraging
- inspiring
- heartwarming
- happy
- fortunate
- lucky
- cheering
3
as in pathetic
deserving of one's pity a heartbreaking attempt to escape that ends in disaster Synonyms & Similar Words
- pathetic
- pitiful
- poor
- miserable
- sad
- sorry
- wretched
- disturbing
- heartrending
- poignant
- horrible
- piteous
- terrible
- pitiable
- inspiring
- emotional
- mournful
- regrettable
- impressive
- rueful
- deplorable
- awful
- touching
- upsetting
- distressing
- affecting
- sorrowful
- moving
- lamentable
- stirring
- grievous
- woeful
Antonyms & Near Antonyms
- unimpressive
- uninspiring