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 last Bravo celebrity who came on this show following a deeply personal and heartbreaking scandal did pretty well for herself on and off the dance floor. — Maggie Fremont, Vulture, 17 Sep. 2026

The doctors’ prognosis after the surgery was that Ponter would be paralyzed from the neck down, and Francey recalled the difficult task of calling her boyfriend’s parents to deliver the heartbreaking news. — Erin Clack, PEOPLE, 13 Sep. 2026

This improvisation of last-minute hope was truly heartbreaking. — Kurt Loder, Rolling Stone, 11 Sep. 2026

No film could be more heartbreaking, yet there are touches of humor throughout. — Matthew Carey, Deadline, 10 Sep. 2026