YOU SAID:
it's hard to say i've never stayed awake when I'm asleep
INTO JAPANESE
それは決して泊まって目を覚まして眠ってるときとは言い難い
BACK INTO ENGLISH
Hard to say when it will never stay awake the sleeping
INTO JAPANESE
無難なときとは言い難い睡眠目を覚まし
That didn't even make that much sense in English.