Doleful
/ˈdəʊlfl/
Definition 1 of 1
Pro Tip 1/3Emotional Weight
Doleful has a strong emotional impact, suggesting deep sadness. 
Her voice had a doleful tone that tugged at everyone's heartstrings.
Pro Tip 2/3Not for Joy
Never use 'doleful' in happy or positive situations, as it implies gloominess. 
At the surprise party, her doleful expression was out of place amidst the laughter.
Pro Tip 3/3Visual Imagery
Often used to describe someone's appearance or gaze to convey their sadness. 
The child's doleful eyes made it clear he was upset about leaving.