I am currently working at one of the largest beverage corporations of the world, and not only they continue to use IE6 but also they methodically inspect every Windows OS update, even if its a security patch, it can be months until they decide to update the network with such patches and updates.
From what you say, I think that you could have experienced what it's known as "sleep paralysis", I remember reading about the subject when going over the same problem in my sleep. Maybe you should take a look on this matter, so you know exactly what you are dealing with, thus not being afraid of this condition.
I like the idea, but I always thought that the action of lending something, involves a somewhat laid back attitude, meaning that if I lend something it might be just because I don't mind when I'm getting that item back. So why would I need an app to follow the people that borrow things from me?
It also helps to break the ice with some smart/funny comment at your friend, but also hoping the comment reaches to the others as well. Sense of humor or good observation can be your ticket in to the network.