I have to say, I've always been curious if, let's say I won one of those Uber Crazy Mega Ridiculous Lotteries (which is impossible, because I never play any kind of lottery), but what if I won something like 500 million dollars?
Being adopted (abandoned as an infant) with no history and no way to find my birth family... I have always wondered how many people would start lining up in order to claim that they were a relative of mine. I would start handing out DNA tests left and right--shoot, they could probably even turn it into a reality show--but even then, I'm a firm believer in family being what you make it rather than DNA, because I don't have any known blood ties.
After reading about all the trouble others with gobs of money have run into, I've always said that the first things I'd buy would be: 1. the best legal team money could buy, because anyone and their mother would try to sue you; 2. a private island, where only my friends and family could find me; and 3. the best set of accountants/financial planners I could possibly hire, because I would invest the money, cap it off with a budget, touch relatively little of the principal, and keep passing it down through the family (and heaven help the person who would squander it and break the chain.)
Churches, charities, and people I would spend it on would be the ones I already spend my time and resources on now and have been with me all my life.
When I was going through a really rough time, I decided to make a major move in order to start a new life, but at the time, I was so depressed that I couldn't do anything more than drag myself to work.
A good friend of mine (despite being married and having her own family to take care of) came over and literally packed up my entire house for me while keeping me company. She literally saved me thousands of dollars in what it would have cost to pay someone else to do it. As soon as I could, I sent her a small gift, but it fell far short of covering everything she did.
If I ever came into that kind of money, one major thing on my list would be to take this friend shopping for a new house as a payback... and let her pick out whatever the hee haw she wanted.
However, in all honesty... She's the kind of person who would say, "Eh. Just come visit me for a week instead."