doleful

American  

[dohl-fuhl] / ˈdoʊl fəl /

adjective

1. sorrowful; mournful; melancholy.

   a doleful look on her face.

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doleful British  

/ ˈdəʊlfʊl /

adjective

1. Archaic word: dolesome.  dreary; mournful

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Other Word Forms

• dolefully adverb
• dolefulness noun

Etymology

Origin of doleful

First recorded in 1225–75, doleful is from the Middle English word dol-ful. See dole ², -ful

Explanation

To be doleful is to be down in the dumps, to have a hole in your soul, to be full of woe. Doleful has nothing to do with a doe, a deer or a female deer. Unless one of those animals has a really sad look in its eyes. Expressions can be doleful, ditto a song or a set of circumstances. You can use the adjective doleful to describe something that is bringing you down, that makes you want to give into gravity or crawl into bed. Doleful is pretty much the opposite of how a ray of golden sun can make you feel.

Example Sentences

When no one is around, the doleful ex-judge listens to Italian gangsta rap, and sometimes even raps along with it, suggesting he isn’t quite the stereotype others assume him to be.

From The Wall Street Journal • Dec. 4, 2025

She was among about 200 mourners accompanying Alanis García on his doleful final journey through his hometown.

From Los Angeles Times • Jul. 28, 2025

That doleful mood pervades these interpretations: a sadly beautiful tone; an emotional climax that evaporates rather than reaching a resolution; a heartbreakingly simple plunk of high keys.

From New York Times • Jan. 25, 2024

Shouldn’t all movies feature a disillusioned astrophysicist, particularly one as charmingly doleful as Stanfield’s character?

From Seattle Times • Jul. 25, 2023

In June 1940, when she went on a long-awaited trip to Mexico, William’s letters were doleful but discreet.

From "The Woman All Spies Fear" by Amy Butler Greenfield