I have never asked my parents for money. They have had to resort to trickery (asking for bank details for some passport stuff) to send me money. I hope to be able to do the same for my kid.
Then again, the person receiving the donated jacket could use the $100 more than the person donating it. It's fun to imagine what I might do if a billionaire gave me a million dollars, or 0.1% of their wealth. Thing is, me giving $5,000 to a homeless person would change their life more than me getting that million dollars.
My mom snuck $100 in a jacket my wife almost donated without realizing.