Answer: Your options are pretty simple. You can continue to bail him out. Or you can stop.

A longtime spendthrift is unlikely to change his behavior. That’s particularly true if he still has people around him willing to give him money, but he may not change even if your entire family cuts him off.

Understanding that you don’t have the power to change your brother is an important, but difficult, first step. You may want to seek help from a counselor or a 12-step group that helps people deal with problem relationships. Since bar hopping is such a big part of his life, you (and your mother) may benefit from attending Al-Anon, the 12-step group for people who have alcoholics in their lives. You can find more information at http://www.al-anon.alateen.org. Another similar group is Codependents Anonymous (information at http://www.coda.org), which aims to help people develop healthier relationships.

I love my parents and want to help, but I don’t want to financially ruin myself or become their money tree. I’ve bailed them out in the past (including several months’ worth of mortgage payments to avoid foreclosure). I am 30 and have a good job, but they seem to think I have an obligation to help them. I resist doing so when I’m told they expect me to pay, but I’m troubled because the situation is affecting their health. How can I establish and maintain proper boundaries?

Answer: No one, including your parents, can dictate what you owe your family. You have to work that out for yourself.

Helping your parents with a life-threatening emergency is one thing. Repeatedly bailing them out of stressful financial situations they’ve created for themselves is quite another, particularly if you’re stinting your retirement savings or going into debt to do so.

So even if you can afford to help, the question remains whether you should. Often people who mismanage money continue to do so if enabled with cash infusions. They don’t have to change, so they won’t.

Your parents, like everyone else, need to learn to live on their current income — not what they used to make or what they hope to make soon. If they can’t cover the mortgage payments, they need to find a cheaper place to live — preferably one that costs less than 30% of what they currently earn. (If your father’s income is extremely irregular, they may need to base their affordable rent on your mother’s income plus whatever he’s reasonably sure he can make each month.)

So instead of giving cash, you might give them a session with a fee-only financial planner (you can get referrals to planners that charge by the hour from Garrett Planning Network, at http://www.garrettplanningnetwork.com) or ask them to meet with a budgeting counselor at a nonprofit credit counseling agency (you can get referrals at the National Foundation for Credit Counseling, at http://www.nfcc.org). You can make these education efforts a requirement of any further financial help from you.

If they can’t manage a decent lifestyle on their incomes despite their best efforts, you may want to step in to help. But just as they weren’t obligated to hand you cash with no strings attached, neither are you required to dole out money freely to them.

photo credit: Dax Melmer

You’ve probably heard that you shouldn’t store things you don’t use. What’s the good china for, after all, if it never graces the family table?

But Harry Rinker, HGTV’s “The Collector Inspector” and author of “Sell, Keep or Toss?,” just gave me another perspective on why we want to use our precious things. Putting the china on the table or using your Grandmother’s candlesticks or reading to your kids from your own childhood books helps your children create memories around these items. When it comes time to pass them down, your children are much more likely to want the stuff that has strong memories associated with it–rather than stuff that’s been sitting in boxes their whole lives.

My husband’s aunt just gave us the Winnie the Pooh books she loved as a child. Although they’re in delicate condition, we’re going to start reading them to our daughter, so she’ll have another way to remember her great aunt.

I’d love to hear what you’re doing to create family memories.

Answer: How nice of your husband’s family to decide how you should spend your money. But just because you appear to be better off than they are does not mean you are obligated to support the family spendthrift.

The situation might be different if your brother-in-law’s life or health were at stake, or if he suffered an unexpected financial blow. In that case, you might want to honor your spouse’s sense of obligation (while perhaps persuading the other siblings to chip in).

In reality, however, what we have is a grown man who can’t figure out how to pay an $11,000 bill without pleading with his siblings for a bailout.

Your spouse should recommend he talk to a legitimate credit counselor about a debt management program that could lower his interest rates. He can get a referral from the National Foundation for Credit Counseling at www.nfcc.org.

If you do lend the money, you of course should formalize it with a written agreement and collateral. But understand that regardless of the precautions you take, the chances of his actually repaying the loan are slim.

You also shouldn’t imagine that the shame of the unpaid debt will deter him from asking for more money the next time he gets into trouble. This man never learned self-reliance, and you won’t teach it to him by giving him more money.