doleful

1. ADJ A doleful expression, manner, or voice is depressing and miserable. 悲痛地[ADV with v]

He gave me a long, doleful look. 他眼神悲痛地久久望著我。

2. dolefullyADV

"I don't know why they left," he said dolefully. “我不知道他們爲(wèi)什麼離開，”他悲傷地說(shuō)。