YOU SAID:

This guy was like talking to a pole or something, and then the pole made him sad

INTO JAPANESE

この男は棒か何かに話しかけるようなものでした、そしてその棒は彼を悲しませました

BACK INTO ENGLISH

This guy was like talking to a stick or something, and that stick made him sad

INTO JAPANESE

この男は棒か何かに話しかけるようなものでした、そしてその棒は彼を悲しくしました

BACK INTO ENGLISH

This guy was like talking to a stick or something, and that stick made him sad