This is actually a much more complicated matter than you'd think primarily because the term "generous" is so damn relative.
You can give your time, your money, your energy....or maybe you give all three.
Giving can be to a charity, a stranger, or to your friends and family.
None are any better than the other and people who brag about what they give are probably doing it for the wrong reasons.
So to summarize the beginning statements, all giving is good, and I try not to judge another's actions in terms of giving especially when we're talking about monetary giving.
However....(you knew it was coming didn't you?)...I am struggling a bit with a few things I've seen lately.
There is NOTHING wrong with being frugal. I am all for it. Most of my frugal friends are the ones that are independent, pay their bills on time, and never ask for hand outs. Sometimes these are my favorite people because (if you know me at all) you know that I LOVE self-reliant people. But, there are times where frugal becomes cheap/tacky and that's just not good for anyone.
There is a lovely friend in my life who I would not call frugal. She gives selflessly to others as often as possible. She is a loving mother and friend and though not always the best with her money, she is a good person with a good heart who gets by just fine. Sometimes she lives paycheck to paycheck and I doubt she rarely has money to donate to a cause. But if you're hosting a fundraiser, she'll be there ready to run that 5k, or help you promote your event, or give you old clothing or baby items for the less fortunate. She could sell a lot of these things and make a good chunk of money - money that she probably needs. But, that's just not her. If she has something she doesn't need, and you do need it, it's yours. No questions asked.
The friend described above has donated endless items to families in need. A lot of these donations were things I asked of her. At the time, I was happy to be able to be the conduit between someone who no longer needed said items to someone who did need them.
Dun dun dun...I now find out that the family who often complains of being poor actually has a good chunk of money in the back (again relative but still). Based on this, and a few examples of being not so generous in the money department, I am at a loss. And here's the sad part, now I don't really want to help them - at least not monetarily. Now, if I had known all along, had they not cried poor, I wouldn't care! It would still be a family that needs something getting it from a friend who would have been happy to give it. But a part of me is slightly angry, that my friend who does the giving has SO MUCH LESS than the family doing the taking.
So here's the moral of the story, if you are not BFF's with someone who is willing to give you something you need, and you have money in the bank that is above and beyond a few months worth of your monthly bills, you absolutely do not just take. Maybe you say thank you with a gift card to Target or Starbucks, maybe you cook a few casseroles, or maybe you send a check that is a small portion of the value - like if you bought the things at a yard sale or thrift store - BUT YOU DO SOMETHING. If you really are broke, then appreciate the generosity of the giver, say thank you and write a card. (This does not apply the same way if it is family or your best friend where you share all your amenities the same way --- but frankly it SHOULD still apply in some small way.)
But don't just be takers people. We're better than that.