How do I say this politely.
Chronic overspending that spans years, decades, cycles . . . can be a symptom of a deeper cause.
It can be linked to bipolar/manic-depression.
http://psychcentral.com/lib/spending-sprees-in-bipolar-disorder/0003295
A normal person will overspend a little occasionally, and will feel remorse and make corrections.
A bi-polar person overspends ALOT throughout the decades, and then will blame others for their overspending/financial situation and/or yells, screams, and gets defensive when asked to be financially responsible. (I know 2 people that are just like this). Then, no one will hear from them for a few months. Then, they go shopping . . . again!
However, many times the person has an entitlement personality, and no depression. They simply believe that they are entitled to their sacred cows, at all costs. They are the opposite of a humble, honest person. They are dishonest with themselves in convincing themselves they can afford something they can't, and with others when they claim bankrupcty and cheat their way out of it by not working. (I know a person that is just like this, too). I have seen these people then try to extract money from others. All of a sudden, a quid-pro-quo deal turns into the person wanting to get paid but doing no more in return. Or, they promise your money to themselves. I had a very large jar of change, and my entitlement person asked to have it 'for a needy person'. Later reported that my change jar had several hundred dollars in it. The needy person was given $100, and the rest went to the entitlement person for something they 'needed.'
Either way, watch your purse around these types of people. They will overstep boundaries and then try to turn you into the witch in the end.