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着我。

2. dolefullyADV

"I don't know why they left," he said dolefully. “我不知道他们为什么离开，”他悲伤地说。