Make it clear to him that the conversation you want to have is serious. When you tell him, say it NO UNCERTAIN TERMS. Leave no room for questions or hope for the future. Put your reluctance to hurt him aside and do this for yourself. Tell him, “I am breaking up with you for good.” Ask him, “do you understand?” If he says he doesn’t, help him to understand: “I don’t want to be with you anymore and I will not be talking to you for an indefinite period of time.” He will try to plead with you.