Question

"My father has been a huge spender his entire life. He always drove nice, new cars. He took trips, and sometimes borrowed to do it. He never paid off his house because he was always borrowing against it. His spending was the source of an ongoing argument between our parents, which we were witness to.

His spending even extended to us children. As teenagers, when we got jobs our father was constantly asking us for money. We reluctantly gave him some of our earnings. 

Once we left home, the money woes were unknown to us, but I suspect they only got worse.

Since Mom died, we've become aware that Dad is still short of money. Basically, he lives on just Social Security. As you can imagine, he struggles to get by. Dad is now looking to us once again to bail him out and support him.

Does this obligation ever end, or are we supposed to support our families and our father? If yes, for how long?"

Answer

I'm so very sorry that your father is unable to live within his resources. It's clear that it's been a source of family strife for decades. Now with your mother gone, he's turning to you.

The short answer is that technically you are not responsible for his debt, his lifestyle, or his future costs. He is responsible for his situation. Unfortunately, this isn't that unusual. Many Americans retire with too few assets to live comfortably in retirement. They live for the moment and save too little.

At this point, what you need to do is decide if you're willing to provide any financial support. As a child living in his house, you didn't have many options. That has changed. There's no judgment here on what you choose to do. One piece of advice I will provide is to make sure you “place the oxygen mask on yourself first before helping others,” as the airlines always say. In other words, maximize your retirement savings, watch your spending, and live beneath your means, before taking on full or partial support of your father. Do not repeat his life.

If you decide to help him financially, set a dollar amount and do not go over it. Be very clear to your father what your limit is, be it $20 a week, $5,000 a month, or a one-time gift. Hold firm. If you don't stick to your guns, the requests will continue.

What you can and should do is tell him (or help him if he lacks the skill) to research what's available in his community or county for low-income assistance. The utilities, the Department of Aging and even retailers have discounts and programs for low-income folks and seniors. It's time he accesses those resources. Frankly, I would require that he do that before you jump in and throw money at the situation.

I realize that this will be hard, and it sounds like a tough love strategy that you'll need to employ. Unfortunately, that's what's needed here unless you're willing to take full responsibility for his lifestyle, and have the means to do so.