YOU SAID:

me and your mom did the most heart wrenching stuff last night

INTO JAPANESE

私とあなたのお母さんは、昨夜最も心を痛めることをしました

BACK INTO ENGLISH

Me and your mother did the most heartbreaking thing last night

INTO JAPANESE

私とあなたのお母さんは、昨夜最も悲痛なことをしました

BACK INTO ENGLISH

Me and your mother did the most heartbreaking thing last night