Woeful means extremely sad, miserable, or pitiful. When something is woeful, it's deeply unfortunate or distressing, far beyond a minor disappointment. A woeful expression shows deep sadness, like when someone hears terrible news. A woeful tale is a story full of suffering and sorrow.

The word also describes something so bad it's almost pitiful. A team's woeful performance means they played terribly, perhaps losing 42 to 0. A student's woeful lack of preparation might mean they didn't study at all for an important test. When used this way, woeful suggests the badness is obvious and hard to ignore.

Woeful carries more weight than simply “sad” or “bad.” It suggests something genuinely distressing or regrettable. You might feel sad about a rainy day, but you'd only call it woeful if that rain ruined something truly important, like an outdoor wedding or the final game of the season. The word has a literary, almost old-fashioned quality that can make situations sound especially serious or dramatic.