I know that this may not be received well but is it at all possible that you are blowing some of this out of proportion? Just asking and posing these possibilities.

When he saw you and spoke, it is possible that he simply did not wish to appear rude by not speaking. And because that put you on alert and you were watching for him to leave, he again felt he needed to speak because you were obviously aware of him.

The Facebook and Linkedin request could, again I say could, have simply been down by allowing them to access his contacts list and send request to everyone in it. He may not really be stalking you and wouldn't you feel like a total fool to request a restraining order for someone who has really not been stalking you, and maybe, just maybe, has totally moved on with his life.