Some years ago now I worked with a group of vulnerable people. I left a long time ago and some of my clients over the years found me on Facebook and message me from time to time. I am mostly fine with this, it's nice they like to update me on their lives or ask advice here and there.
I have one who since I have become single (divorce) seems to try to flirt with me. He is still a very vulnerable person and I feel quite awkward with his communication. I think it would be quite devastating to him if I simply didn't ever speak to him but I'm at the point of needing to establish boundaries without humiliating him
I've tried joking that he's far too young for myself. Until now I've sort of batted away his comments and just made sure I haven't responded to anything in a flirty manner back so if he puts xxx I just say "take care" or what have you
I'm at the point though of feeling quite uncomfortable with this persistent idea that he can try his luck here and there when for years I have never given him any impression that anything will ever happen yet he keeps popping up every few weeks now with what if he was any other person I would have a long time ago said please don't do that to me rather than simply ignored or tried to change the subject
If I say it too gently, it will be ignored. If I say it too harshly - I risk him self harming quite badly
I'm no longer in any professional capacity to him and haven't been for years but I am very worried that if I handle this badly it will factor as a major thing in his life due to my past professional relationship with him. My old clients do see me as someone who was fairly significant in their lives (trying to not completely out myself but explain)