1.Definition: (informal to emphasize how bad it is) beyond hope of management or reform

"She handed me a hopeless jumble of papers", "He is a hopeless romantic"

2.Definition: certain to fail

"The situation is hopeless"

3.Definition: of a person unable to do something skillfully

"I'm hopeless at mathematics"

4.Definition: without hope because there seems to be no possibility of comfort or success

"In an agony of hopeless grief", "With a hopeless sigh he sat down"