Synonyms of rueful

rueful

adjective

ˈrü-fəl 

1

as in mournful

expressing or suggesting mourning

the rueful faces of friends and family who had gathered to pay their last respects

Synonyms & Similar Words

• mournful
• weeping
• heartbroken
• funeral
• bitter
• melancholy
• sad
• anguished
• grieving
• sorrowful
• regretful
• doleful
• wailing
• tearful
• plaintive
• lamentable
• lugubrious
• somber
• sorry
• agonized
• unhappy
• aching
• dolorous
• plangent
• woeful
• depressed
• crying
• funereal
• morbid
• bleak
• dark
• elegiac
• bewailing
• deploring
• bemoaning
• pathetic
• dolesome
• dejected
• disconsolate
• downcast
• glum
• heartsick
• crestfallen
• keening
• miserable
• dispirited
• woebegone
• forlorn
• despondent
• gloomy
• moody
• darkening
• careworn
• inconsolable
• sullen
• pessimistic
• piteous
• morose
• desolate
• groaning
• brokenhearted
• cheerless
• downhearted
• gray
• howling
• bleeding
• moaning
• saturnine
• joyless
• black
• low-spirited
• heartsore
• dismal
• low
• suffering
• dirgelike
• wretched
• dreary
• comfortless
• triste
• bawling
• yammering

Antonyms & Near Antonyms

• triumphant
• happy
• joyful
• cheerful
• delighted
• cheery
• bright
• smiling
• laughing
• joyous
• mirthful
• merry
• lighthearted
• blithe
• optimistic
• jolly
• buoyant
• exulting
• rejoicing
• blissful
• hopeful
• encouraging
• glorying
• cheering
• rapturous
• ecstatic
• giddy
• jocund
• rhapsodic
• euphoric
• blithesome
• heady
• exhilarated
• elated

2

as in sorry

feeling sorrow for a wrong that one has done

a rueful youth who had come to ask for forgiveness for online bullying

Synonyms & Similar Words

• sorry
• ashamed
• remorseful
• regretful
• apologetic
• contrite
• repentant
• penitent
• sheepish
• compunctious
• weeping
• plaintive
• mournful
• sorrowful
• shamefaced
• lugubrious
• dolorous
• wailing
• woeful
• grieving

Antonyms & Near Antonyms

• unapologetic
• remorseless
• unrepentant
• pitiless
• cruel
• ruthless
• impenitent
• merciless
• unmerciful
• shameless
• unashamed
• compassionless

3

as in pitiful

deserving of one's pity

the rueful, desperate poverty of people in parts of the Third World

Synonyms & Similar Words

• pitiful
• pathetic
• poor
• miserable
• wretched
• sorry
• piteous
• pitiable
• sad
• disturbing
• mournful
• heartbreaking
• horrible
• terrible
• impressive
• lamentable
• poignant
• regrettable
• emotional
• heartrending
• inspiring
• deplorable
• awful
• sorrowful
• moving
• touching
• stirring
• distressing
• grievous
• affecting
• upsetting
• woeful

Antonyms & Near Antonyms

• unimpressive
• uninspiring

Example Sentences

Recent Examples of rueful

Her lips pressed in a rueful grin. — Richard Greenberg, Los Angeles Times, 6 Feb. 2026

Through Eisenhower’s ruminations, Hellesen’s script notably engages with passages that land with rueful resonance to today’s ears, drawing applause from Sunday evening’s opening night crowd. — Christopher Smith, Oc Register, 20 Jan. 2026

Fritz, who has come as close to winning a major in the past two years as anyone else in the chasing pack, gave that rueful smile at the ATP Tour Finals, the season-ending tournament for the best eight men’s players in the world. — Charlie Eccleshare, New York Times, 19 Jan. 2026

But most of Guy’s stories are told with the rueful smile of a man who knows his days of being underappreciated and underpaid are behind him. — David Browne, Rolling Stone, 30 Nov. 2025