Dear Helaine: I like to be generous. A friend and I went to dinner at a restaurant at my recommendation. I tried to pay for our dinner with some gift cards I had. She tried to make me use them only on myself. She spoiled my enjoyment of our dinner. Why couldn’t she just enjoy the dinner and the fact that I wanted to use my gift cards on her? -- Generous Pal

Dear Generous Pal: You mean well, you really do. You wanted to go to a particular restaurant, and you wanted a friend to join you. You wanted to use a gift card, and you absolutely did right to offer to cover the cost of the meal. Personally, I think it’s a bit tacky to use a gift certificate to pay for your share of the bill for a meal and not make that gesture. Clearly, you agree with me!

However, here’s what you can’t do: You can’t force anyone to accept your generosity. No matter how much you wanted to pay the bill, no matter if the person you were dining with could use a bit of financial help, there’s no way. We can’t control other people. As long as you tried to do the right thing, I don’t think you should have allowed it to impact your enjoyment of the meal and time with your friend.

In the future, I would suggest explaining in advance that you have a gift card and would like to use it to cover the both of you. This way, you aren’t putting anyone on the spot, and you can enjoy the meal however you both pay for it.

(To ask Helaine a question, email her at askhelaine@gmail.com.)

(EDITORS: For editorial questions, please contact Sue Roush at sroush@amuniversal.com)

Hi Helaine: I’m 25 years old and have around $50,000 in student loan debt from undergraduate and graduate school. My mother recently passed away, and I’m inheriting about half a million dollars in various forms of assets. There are liquid assets, some real estate and an annuity. Should I leverage part of this inheritance to pay off my student loan debt in full?

I’m tempted, but have three reasons I’m hesitant to do so. What if Congress passes retroactive student loan forgiveness legislation? Or would I be better off keeping my inheritance in its current form? What are the tax consequences of selling? Finally, my hope is that this inheritance sets me up for retirement. Let me know what you think! -- What to Do?

Dear What to Do: First, let me say I’m terribly sorry to hear about your mother’s passing. I’m sure this is a difficult time for you and your family, and I would urge you to be good to yourself and not rush into any decisions. But here is one thing you don’t need to worry about: The odds of Congress passing retroactive student loan relief are less than zero, sad to report. At the moment, the U.S. government can’t even bother to ensure that borrowers promised relief via the public service loan forgiveness program receive it.

So that begs the question of what to do next. I am all but certain you’ll be rejiggering this portfolio to reflect both your age and risk tolerance. I see no reason why you can’t take some of the funds and pay off the student loans early while you are at it. The question is how to do it. What kind of penalty will you pay if you sell the annuity? Are you planning to live in the real estate you inherited, or do you hope to rent it out? If the latter, are you up for being a landlord, or is the income you generate going to be more trouble than it’s worth?

Finally, you will need to pay capital gains taxes for any uptick in value of the investments you sell from the time your mom died to when the property or investment is no longer yours. I’d suggest sitting down with a certified financial planner, working out the numbers, and taking it from there.

(To ask Helaine a question, email her at askhelaine@gmail.com.)

(EDITORS: For editorial questions, please contact Sue Roush at sroush@amuniversal.com)

Dear Helaine: My husband and I own a home and have put two children through college. We carry financial debt for that, but we have frozen payments for a while.

My 10-year-old business has taken a nosedive, and I lost money last year. I am looking for a job, but there are not many companies wanting to hire a 60-year-old woman. In addition, we’ve needed to support my husband’s parents. As a result of all this, we have $75,000 in debt.

Our house is worth just under $900,000. We can’t refinance because I didn’t earn income last year. We’ve been trying to sell it for a few months, but we’ve received no firm offers. We owe $575,000 on it. I really don’t want to declare bankruptcy. What do you suggest? -- Desperate but Not Underwater

Dear Desperate: Take a deep breath. You need to think long and hard about your current reality. The deus ex machina of a one-time financial windfall is not a long-term solve.

While it seems like your business collapse is the cause of your financial woes, in fact, you and your husband have been living at the financial edge for a long time. It seems obvious in retrospect you couldn’t afford to support your in-laws, nor could you afford all the college loans you took on.

My advice: Meeting with a bankruptcy attorney is not the same as committing to filing for bankruptcy. So do it. Also sit down with a debt counselor. You need to slowly but surely examine and weigh your options.

I’m not convinced selling the home is the right step. Where do you plan to live afterward? Can you afford to rent where you are now? Or will you ultimately need to move to a cheaper geographic region, putting your husband’s earnings in jeopardy?

And, since this is your only asset, what are you planning to tap into at retirement? Will you really invest the funds you net from selling the home and paying down your debt, or will you slowly but surely spend the money in yet another attempt to keep up with what you think you should do? I can also all but guarantee you will not net as much from this home as you think, for the obvious reason that if it was worth what you think it is, it likely would have sold by now.

One other thing: It’s easy to say you’ll work till you drop, but you are learning a hard lesson right now -- many people are forced out of the workforce early due to events beyond their control. As a result, you need to make a plan.

(To ask Helaine a question, email her at askhelaine@gmail.com.)

(EDITORS: For editorial questions, please contact Sue Roush at sroush@amuniversal.com)