painful ·adjective (EMOTIONAL)

看着她儿时的画作，痛苦地提醒着那些更快乐的时光。

Looking at her childhood drawings was a ___painful reminder of happier times.

输掉冠军赛对整个队伍来说是一次痛苦的经历。

Losing the championship game was a ___painful experience for the whole team.

看着亲密的朋友一次又一次犯同样的错误，令人痛苦。

It's ___painful to watch a close friend make the same mistakes over and over.