Daily Chinese Idiom Guessing Game
To not know whether to laugh or cry; to be in an awkward situation that is both funny and frustrating.
哭也不好，笑也不好。形容很尴尬。
元·高安得《皮匠说谎》好一场恶一场，哭不得笑不得。”
When he accidentally sent the email to his boss instead of his friend, he was literally in a 哭笑不得 situation.