doleful
Americanadjective
adjective
Other Word Forms
Derived Forms
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.
Vocabulary lists containing doleful
100 SAT Words Beginning with "D"
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"The Lady, or the Tiger?" by Frank R. Stockton
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"Sinners in the Hands of an Angry God" by Jonathan Edwards
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Example Sentences
Examples are provided to illustrate real-world usage of words in context. Any opinions expressed do not reflect the views of Dictionary.com.
With his doleful singing voice and a prolific work rate, he's transformed the sound of música urbana, combining elements of trap, hip-hop and R&B with the traditional sounds of Latin pop.
From BBC • Feb. 5, 2026
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
His agent has booked him a gig as “Sad American,” a role he can easily play with his looming height, doleful eyes and a heart he wears on his sleeve.
From Los Angeles Times • Nov. 21, 2025
Shouldn’t all movies feature a disillusioned astrophysicist, particularly one as charmingly doleful as Stanfield’s character?
From Seattle Times • Jul. 25, 2023
Beneath his doleful eyes the skin was already darkening in pouches.
From "Middlesex: A Novel" by Jeffrey Eugenides
Definitions and idiom definitions from Dictionary.com Unabridged, based on the Random House Unabridged Dictionary, © Random House, Inc. 2023
Idioms from The American Heritage® Idioms Dictionary copyright © 2002, 2001, 1995 by Houghton Mifflin Harcourt Publishing Company. Published by Houghton Mifflin Harcourt Publishing Company.
