I guess a lot of it depends on what its for.
On the holiday issue, let's consider this for a second. (this is a future hypothetical)
I'm in my 50s and my wife and I want to go to Hawaii with my son, his wife and kids for christmas.
My son clearly can't afford it but it would mean a lot to me for us to spend this holiday together since I get to see my grandchildren etc... Why wouldn't I pay for that if I have the financial means to do so, it is after all, for me.
I see this totally different from "Hey son, here's 10 grand, go to paris".
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