YOU SAID:

a kind-hearted but creepy-looking old dude informed me of a extreme situation he was in at some point

INTO JAPANESE

心は優しいが気味の悪い老人が、ある時点で彼が極限状態にあったことを教えてくれた

BACK INTO ENGLISH

A kind-hearted but creepy old man told me that at one point he was at his limit

INTO JAPANESE

気さくで気味の悪いおじいさんが、ある時点で彼は限界に達したと私に言いました

BACK INTO ENGLISH

A good-natured creepy old man told me that at one point he had reached his limit

INTO JAPANESE

気さくな気味の悪いオッサンが、ある時点で限界に達したと私に言った

BACK INTO ENGLISH

Good-natured creepy old man told me he hit his limit at some point

INTO JAPANESE

気さくな気味の悪いオッサンが、ある時点で限界に達したと私に言った

BACK INTO ENGLISH

Good-natured creepy old man told me he hit his limit at some point