I worked with a man a while back who definitely had some issues with managing his finances. His wife only worked here and there at part-time jobs for a couple weeks at a time, citing "medical issues" that kept her from standing/sitting/being awake/etc for too long a period of time. He only worked part-time himself and was reluctant to take a second job because "who would watch the kids?" (Keep in mind, his wife would be home to watch them, but apparently, her "medical issues" didn't allow for that kind of work, either.)
Well, this man and his wife have 2 kids, one of which they decided had amazing football talent, and in order for him to have a shot at becoming a future NFL player, they decided to pick up the family and move to a different school district that had a football team known for its success and the number of players that were offered college football scholarships. This same school district is also known for having some of the highest taxes and being one of the most expensive places to live in our area.
Soooo.... Co-worker sends out an email to all his friends, acquaintances, and anyone he might possibly have seen on the street. Pours out the whole story about their move and flat out ASKS FOR DONATIONS to subsidize their move, the deposit and first month's rent on their (much more expensive) apartment, and new furniture for their new (much larger and much more expensive) apartment.
Fast forward several months. Co-worker sends out another email about how rough things have been since their move -- his commute to work has doubled, as have his commuting costs. Wife can't (more like won't) work, and they're in dire straits, having moved to this very expensive apartment in this very expensive school district to try to help their son get a football scholarship. To top it all off, Christmas is coming and his kids REALLY DESERVE to have a nice Christmas. Would any of us like to donate to their cause to help make sure his kids get the (insert name of very expensive, popular, impossible to find toys of the season here) that they want and deserve for being such good kids? Co-worker managed to even send this email to our boss.
He was fired not long after he hit the send button.