I was able to identify with one of the general themes that Machiavelli harps on: that you have to acknowledge the gap between the way people ideally should behave and the way they actually do behave, before deciding how to act or respond towards them. When he discusses generosity, this hit close to home for me. Ideally, one would think that everyone should strive to be generous--but this is not so! It is in fact true that if you attempt to be overly generous, people will take advantage of your giving spirit and soon you will have nothing left for yourself.
Growing up, I had some very "needy" friends, always borrowing but never paying back, and I was generous enough to loan. Eventually those friendships soured, but not before I was left hanging with a dwindling bank account. It was a hard lesson to learn (especially because it involved money), but an important one. And I understand that being generous ("giving") is different from "borrowing," but I think the same principle applies. Unless you have the resources to be generous with other people's money, it really is not worth it in the long run to [monetarily] seriously help someone out, especially people who are not trustworthy or even show the slightest hint of being ungrateful.
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Money is the root of all evil and so many times I find this to be true. People do take advantage of the generous, but when money is involved it makes the situation so much worse. Why can't everyone just be helpful and honest, the world would be so much easier to live in.
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