If you need a reason to be depressed today, PlaySpent is a great way to get there. You will live through a month of credit card debt, disappointing children you didn't know you had, experiencing the death of loved ones and fixing your crappy used car. The upside, however, is you'll learn a lot about making do with what you've got, the tough decisions you'll have to make when you don't have a decent income, and what it's like when things are nearly as bad as they can get.
I managed to make it through the month with an IOU and a repossessed car, but I think I still managed to make it with my integrity intact. I did have to miss a friend's wedding, though. While this site is clearly a means of soliciting donations and assistance to the Urban Ministries of Durham, who help the poor, it's also an interesting way to see where you might end up if you're not careful with your finances.