demoralizing, unhappy, dismal, sad, heartbreaking, miserable, upsetting, terrible, painful, tragic, demoralising, discouraging, dispiriting.
dejecting (part of speech: verb)
dissuading (part of speech: verb)
disappointing (part of speech: verb)
de-motivating (part of speech: verb)
The old dame said it was disheartening,
indeed, trying to make companions of one's children when they showed such a low order of intelligence for it.
- "Somewhere in Red Gap", Harry Leon Wilson.
It was disheartening
to hear that hope, at her age, began and ended within such narrow limits as these.
- "The Legacy of Cain", Wilkie Collins.
On the whole, the grand attitude in which Buonaparte had left the Republic when he embarked for Egypt, was exchanged for one of a far humbler description; and, in fact, as has been intimated, the general disheartening
of the nation, by reason of those reverses, had been of signal service to Napoleon's ambition.
- "The History of Napoleon Buonaparte", John Gibson Lockhart.