I have given away a couple of bags to my sister and mom, but when I see them wear it, I usually think, "Damn I gave THAT away??!??"
It sounds weird, but I've always hesitated donating bags to Goodwill because I wonder if the recipient will end up getting mugged or robbed because they're carrying a nice bag when they live in a bad area. I only think this because I read somewhere about kids saving up to buy nice sneakers/clothes but getting them literally ripped off their feet/back the day they wear them.