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.

—William Thackeray

ruefully

ˈrü-fə-lē 

adverb

ruefulness noun

Synonyms of rueful

• mournful
• weeping
• heartbroken
• funeral
• bitter
• melancholy

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

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

Marcus Semien — a 35-year-old second baseman less than a month into his first season in Queens — said, cracking a rueful smile. — Hannah Keyser, CNN Money, 22 Apr. 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

Metcalf and Pullman are both wonderful in their shuffling ordinariness, reenacting long-obsolete parental dynamics with a kind of rueful, hopeful denial. — Guy Lodge, Variety, 13 Feb. 2026

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