Have you ever made a stupid purchase? Was your retirement plan heavily leveraged in Beanie Babies? Did you have a timeshare in Abbottabad? Well, if you come clean about your questionable spending, via video, you may win $1,000. Spendster.org is giving away 53 cash prizes ranging from $100 to $1,000. As of this posting, there are only 66 entries. Press record on that video camera and spill your guts! The contest runs through May 25, 2011. Visit Spendster for more details.