YOU SAID:
My roommate shows me dragons when I am crying
INTO JAPANESE
泣いているときにルームメイトがドラゴンを見せてくれる
BACK INTO ENGLISH
My roommate shows me the dragon when I'm crying
INTO JAPANESE
泣いている時にルームメイトがドラゴンを見せてくれる
BACK INTO ENGLISH
My roommate shows me the dragon when I'm crying
That didn't even make that much sense in English.