YOU SAID:

I’ve worked with him five times and I can’t get him to message me

INTO JAPANESE

私は5回彼と仕事をしましたが、彼に私にメッセージを送ってもらうことはできません

BACK INTO ENGLISH

I worked with him five times but I can not get him to send me a message

INTO JAPANESE

私は彼と5回仕事をしましたが、私に彼にメッセージを送ってもらうことはできません

BACK INTO ENGLISH

I worked with him five times but I can not get him to send me a message