How to deal with his obvious cluelessness? I don't know your situation but if you have to deal with him, you should be upfront and honest. That does not mean be mean and derogatory but just tell him that it's inappropriate for you to keep in touch anymore and you're not comfortable with it. Put it out on the table. If he doesn't like that and keeps it up, the ball is in your park, at least he knows if you block him completely or ignore him, why it is. Also I don't believe in being misleading. Why even bother putting up the facade that everything is ok? That's just unfair to him, no matter what you think of him. You're stringing him along even if he's not thinking you'll get back together, he thinks you're friends and you're not.