失恋是痛苦的。

Shīliàn shì tòngkǔ de.

A breakup is painful.

他的表情很痛苦。

Tāde biǎoqíng hěn tòngkǔ.

His expression looks pained.

这场车祸为他留下痛苦的回忆。

Zhè chǎng chēhuò wèi tā liúxià tòngkǔ de huíyì.

This car accident left him with painful memories.