I kind of warmed a little to jgnat's comment, somehow, where she says, "I wouldn't agonize so much about demons and God's will. He knows your heart and as soon as it is not doing you any good, stop it. As for demons, Witnesses fear churches for the same thing. I see two groups mutually fearful of 'demons'...". Well yes, but - dunno.
Although there's truth in what she says, the WT organisation is all about deception. If the WT is not the truth, could the deceiver, the father of lies be behind it? Could one aspect of the deception be "don't go to churches - that's where the demons are"? It is precisely in churches, good ones anyway, where the truth is to be found.
I believe that what we read in 1 John 5:19 is right. The whole world does lie in the power of the evil one. The Watchtower is a spiritual counterfeit and of course under his power too. If it appears we're a threat to people in his thrall (good word, that, must use it more often) he's going to retaliate. No surprises there. Without getting all extreme and spooky now, we are in a spiritual fight or Paul wouldn't have written what he did about the weapons of our warfare. We can even come of second best from time to time, I have - but this can be dealt with as we or others pray. I'm not sure we should stop something if it is not doing us any good, necessarily. If we get demonic flak we must be doing something right.
Faithful Witness, all this is not to say that you should continue seeing the elderette and colleague. It might well be an idea to call the discussions off. Look to God for his leading in the matter. I'll be happy to pray too, if you like, that he would reveal unmistakeably to you what he has in mind.