Things that discourage you, or make you lose confidence, are demoralizing. It can be demoralizing to study hard for a test and do badly on it.

When you are rejected — getting turned down for a job or a date or a scholarship — it's demoralizing. If people whose opinions you value put you down or belittle you, that's demoralizing too. A more old-fashioned meaning of the word is "corrupting someone's morals," from the French démoraliser, which is thought to have been coined during the French Revolution.

Definitions of demoralizing

adj destructive of morale and self-reliance

demoralising, disheartening, dispiriting
depriving of confidence or hope or enthusiasm and hence often deterring action

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