这张旧照片勾起了痛苦的回忆。

The old photograph brought back ___painful memories.

当我换工作时，我经历了一个痛苦的决定。

I went through a ___painful decision when I changed jobs.

当她不得不说再见时，那是一个痛苦的时刻。

It was a ___painful moment when she had to say goodbye.