It's easier to be generous with complete strangers I think. Like, giving a kid a water bottle if you have an extra one when the kid is thirsty (with parent's permission). Or buying the person in line behind you their coffee. Or opening the door for a mom struggling with a stroller.
It's harder to be truly generous with people close to you... because it's like, you have to give more. And it's not really generosity on your part if you agree to grant them something they asked you for, even if it's at cost to you... because, even though you don't admit it, deep down, you are expecting something in return - mostly gratitude or thanks. Which is still something in return.
I had a friend once - very close friend - who asked me to cosign on a loan so he could go to med school - this loan cost more than my house. And I don't have a small house. I said no. If I said yes, it would not be out of generosity... because I would expect in return that he doesn't screw me over (not pay his loan)... and if he becomes a doc and I get broke... he would reciprocate. The whole situation was a recipe for failure, because he was irresponsible with money to begin with, so I decided to not enable him. Me saying no was not me being ungenerous.
I've also bought my brother a car before, actually two cars. But that's not being generous, because I totally expect my brother to not give me **** and be grateful I bought him a car. And I totally expect that if I ever run into financial (or emothional) hardship, my brother is there for me. So that's not generosity either.
The last time I remember being truly generous was when it cost me not one cent. I wrote a letter to one of my other brothers to let him know that I loved him, thought of him, and was glad he was in my life. Another time was when I wrote my in laws, sent a bunch of pictures (that I carefully selected and printed out) of our family vacation with them, and told them I truly had a great time and looked forward to more great memories in the future (and I meant it).
So times when I've truly felt that I was generous didn't really cost me a dime monetarily.
Those are some examples of generosity in my definition of how I understand the term. Others may disagree with me, and that's really ok. I'm not an expert on generosity so I don't claim to have a monopoly over what it is.
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