YOU SAID:

How many times do I have to tell you to tuck your shirt in?

INTO JAPANESE

シャツを中に入れるように何回言えばいいですか？

BACK INTO ENGLISH

How many times should I tell him to tuck his shirt in?

INTO JAPANESE

彼にシャツを中に入れるように何回言えばいいでしょうか？

BACK INTO ENGLISH

How many times should I tell him to tuck his shirt in?