To not know whether to laugh or cry
Refers to when someone doesn't know how to respond to a situation; to be frustrated and amused at the same time
Neutral
他经常干些让人哭笑不得的蠢事 | Tā jīngcháng gàn xiē ràng rén kūxiàobùdé de chǔn shì
He often does foolish things that leave people not knowing how to respond
[Source]
警察们听小偷说他偷窃是因为想过得体面,他们真是哭笑不得 | Jǐngchámen tīng xiǎotōu shuō tā tōuqiè shì yīnwèi xiǎng guòdé tǐmiàn, tāmen zhēn shì kūxiàobùdé
When the police heard the thief say he was stealing because he wanted a good life, they didn't know whether to laugh or cry
[Source]
To not know whether to laugh or cry
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《皮匠说谎》(Pí Jiāng Shuō Huǎng), a work by Yuán Dynasty (元, 1279-1368) author 高安得 (Gāo Ān Dé).
This chengyu comes from a line in the work listed in the "Origin" section above