Synonyms of heartbreaking

heartbreaking

adjective

ˈhärt-ˌbrā-kiŋ 

1

as in sad

causing unhappiness

a heartbreaking story of a family torn asunder by war

Synonyms & Similar Words

• sad
• depressing
• pathetic
• unfortunate
• mournful
• tearful
• melancholy
• saddening
• disturbing
• heartrending
• teary
• dismal
• sorry
• dreary
• drear
• distressful
• distressing
• lamentable
• deplorable
• poignant
• disquieting
• touching
• moving
• discomforting
• grievous
• woeful
• perturbing
• disheartening
• discouraging
• affecting
• dispiriting
• discomposing

Antonyms & Near Antonyms

• happy
• glad
• inspiring
• cheery
• uplifting
• heartening
• stimulating
• stirring
• delightful
• pleasant
• enjoyable
• satisfying
• welcome
• cheering
• heartwarming
• pleasurable
• agreeable
• pleasing
• thrilling
• exhilarating

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
• terrible
• shocking
• distressing
• horrible
• disturbing
• regrettable
• painful
• deplorable
• sad
• lamentable
• unsettling
• grievous
• heartrending
• woeful
• sickening
• distressful
• unlucky
• awful
• dire
• disastrous
• poignant
• dreadful
• pitiful
• miserable
• unbearable
• fearful
• troublesome
• traumatic
• horrifying
• severe
• alarming
• crushing
• overwhelming
• touching
• harrowing
• moving
• doleful
• piteous
• vexatious
• excruciating
• wretched
• affecting
• intolerable
• calamitous
• perturbing
• ruthful
• sharp
• raging

Antonyms & Near Antonyms

• rewarding
• gratifying
• satisfying
• pleasing
• encouraging
• comforting
• heartening
• inspiring
• happy
• fortunate
• lucky
• heartwarming
• 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
• wretched
• sorry
• sad
• disturbing
• pitiable
• piteous
• horrible
• heartrending
• terrible
• emotional
• rueful
• inspiring
• impressive
• poignant
• regrettable
• deplorable
• lamentable
• mournful
• awful
• distressing
• moving
• touching
• sorrowful
• stirring
• upsetting
• affecting
• grievous
• woeful

Antonyms & Near Antonyms

• unimpressive
• uninspiring

Example Sentences

Recent Examples of heartbreaking

The end result is a sharp, unapologetic art-house novel full of gravitas, humor and heartbreaking revelations about the Black American experience and the thousand and one ways our nation can shatter Black souls. — Literary Hub, 8 Oct. 2026

Now, all of this follows Parton’s longtime driver, Jason Pirro, opening up about her heartbreaking death. — Allison Degrushe, StyleCaster, 7 Oct. 2026

The state of Connecticut formally into their General Assembly entered the heartbreaking details of more than three dozen local deaths strongly linked to energy drinks. — Kent Sepkowitz, STAT, 5 Oct. 2026

Minutes before he was sentenced Monday to life in prison for the murder of his wife, Caleb Flynn sobbed as his in-laws read letters written by his two daughters, asking him heartbreaking questions about their mother’s death. — Nicki Brown, CNN Money, 5 Oct. 2026