rueful

adjective

rue·​ful ˈrü-fəl 

1

: exciting pity or sympathy : pitiable

rueful squalid poverty … by every wayside

—John Morley

2

: mournful, regretful

troubled her with a rueful disquiet

—W. M. Thackeray

ruefully

ˈrü-fə-lē 

adverb

ruefulness noun

Synonyms

• aching
• agonized
• anguished
• bemoaning
• bewailing
• bitter
• deploring
• doleful
• dolesome
• dolorous
• funeral
• grieving
• heartbroken
• lamentable
• lugubrious
• mournful
• plaintive
• plangent
• regretful
• sorrowful
• sorry
• wailing
• weeping
• woeful

Examples of rueful in a Sentence

He gave me a rueful smile and apologized.

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

Recent Examples on the Web

Baker clearly respects and admires Ani, and looks with rueful empathy at the severe orders and fearsome threats under which the three tough guys labor, the harsh yet frivolous upbringing that has left Vanya a terrified emotional baby. —Richard Brody, The New Yorker, 23 Oct. 2024

But most of my friends grimace and then, after a rueful joke, move on to other topics. —Vinson Cunningham, The New Yorker, 11 Oct. 2024

The book also has a complicated, somewhat rueful take on race. —Charles McGrath, The Atlantic, 8 Oct. 2024

Arrogantly rueful, Hartnett’s vicious killer has a flair for the dramatic, revealing, in the film’s final throes, to lead a semi-charmed kinda life. —Nicholas Bell, SPIN, 4 Sep. 2024

Word History

First Known Use

13th century, in the meaning defined at sense 1

Kids Definition

rueful

adjective

rue·​ful ˈrü-fəl 

1

: exciting pity or sympathy

2

: mournful sense 1, regretful

ruefully

-fə-lē 

adverb