What are the ten most expensive things you have paid for? What are the ten things you have bought that made you happiest? Is there overlap? On both my lists:
International travel: Belize, Western Europe, and Japan especially.
Designer clothes: Because I am vain and it gives me great pleasure to look stylish. And because I like beautiful, well-made things with high uses to dollars ratios.
Furnishings for my current house: This is the first place that I have really made my own through choice of decor and furniture. I don't know why anyone would have a home with white walls in every room anymore.
My car: Not having your own car really sucks! And hand-me-down cars are fine, but it's great to be able to pick something out on your own, so that it meets your needs and wants.
Books: I try to go to the library but I've probably spent thousands on books despite my cheapskate intentions.
Basically, it looks like my best expenditures have been either experiential (reading, traveling) or expressive (clothes, furnishings, picking my car). You?