He was wretched when he failed the entrance exam again.

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He was wretched when he failed the entrance exam again.
He was wretched when he failed the entrance exam again.

He was wretched when he failed the entrance exam again.
当他又一次在入学考试中失败,他很痛苦.
或者更书面语一点:当他又一次在入学考试中失利,他灰心丧气.