'I'm concerned that my card issuers might freeze or flag the cards when they suddenly see an extraordinary number of transactions'

"I would arrange everything privately, in coordination only with the management and staff of each restaurant." (Photo subject is a model.)

Dear Quentin,

I lost my beloved husband earlier this year after a long illness. I miss him profoundly. His passing was not unexpected, but honoring his simple, decent memory is very important to me in the days and years ahead.

My husband enjoyed humble pleasures, and he had two favorite fast-casual restaurants where the food was good, the patrons were kind, and the staff were simply salt-of-the-earth people. With that in mind, I have an idea for a small tribute to him.

In 2027, on his birthday in April and in September, on the anniversary of our first date, I would like to pay for every order placed by walk-in customers - from open to close - at each of these two restaurants.

No online orders, and no fanfare or publicity. I would arrange everything privately, in coordination only with the management and staff of each restaurant. I've researched the revenues of both locations and can comfortably afford to do this.

My husband enjoyed humble pleasures, and he had two favorite fast-casual restaurants where the food was good.

It would be my own little way of honoring my husband: supporting two local businesses he loved and, for one day, treating the people who patronize them with the same simple generosity and kindness that characterized him.

My question is: How would I best arrange the logistics with each restaurant, and what would be the most reliable way to handle payment? I could certainly put the charges on my credit cards as customers came through.

However, I'm concerned that my card issuers might freeze or flag the cards when they suddenly see an extraordinary number of transactions. I could also put down a substantial good-faith deposit and settle the balance at the end of the day if the total exceeds the deposit.

Beyond those possibilities, though, I'm completely stumped. I'd love to hear any practical suggestions for structuring this so that it is easy for the restaurant, seamless for the staff and customers, and doesn't create unnecessary headaches for anyone.

A Kind Remembrance

Related: 'This guy grifted me hard': My date chose an exclusive L.A. restaurant. After dinner, he accepted my credit card - and we split a $600 bill. Shouldn't he have paid?

You can email The Moneyist with any financial and ethical questions at qfottrell@marketwatch.com. The Moneyist regrets he cannot reply to questions individually.

You would be relying on the restaurant management not to spill the beans to regular customers and employees.

Dear Kind,

Your idea is pretty special, but perhaps needs a little finessing.

My main piece of advice would be for you to put a lid - excuse the pun - on how much you spend. If you get an estimate from each restaurant that they do, say, $10,000 worth of business that day, you could make sure that the day's transactions do not exceed that.

There are a lot of questions that would need answering: Does your generosity include sales tax and tips? What happens if somebody orders $500 worth of food for a group or $500 worth of booze, and you suspect they got wind of your charitable endeavor? Do you want to cover tips?

You would also be relying on the restaurant management not to spill the beans - apologies once again for the pun - to regular customers and employees. You could have customers showing up ordering a feast of fillet steaks because they got an inside tip on your generosity.

For that reason, consider matching receipts rather than giving your credit cards to employees. Too much could go wrong. Also, think about whether you want to cover alcoholic drinks. If word got around, a lot of Dom Perignon might miraculously be in demand that day.

By paying the customer's bills, they get to have a free meal, but the restaurant still gets paid for the day's receipts.

Ideally, I'd like you to balance the emotion and romance and beauty of your generosity with the practicality of implementing it, while taking the peculiar habits of human beings into account (chief among them, people love a bargain, and news of a $0 meal will spread like wildfire).

Perhaps tell the restaurant management something along the lines of: "I would like to cover the cost of every walk-in customer's food and soft drink, anonymously and without publicity. I want your staff to operate exactly as usual. I will match their bills."

But don't be surprised if the unusual event ends up in the local paper. You can control very few things in this life, and word-of-mouth news is chief among them. You may decide to do a trial run for your late husband's birthday and maybe try something different for your anniversary.

One more thought: By paying the customer's bills, they get to have a free meal, but the restaurant still gets paid for the day's receipts. If these restaurants are owned by a giant global conglomerate, you're also giving that money to that company.

Related: 'We fear financial exploitation': Who will manage our finances if my wife and I become incapacitated?

Remembering the staff

I also wonder whether it would mean more to direct your largesse towards the wait and kitchen staff rather than random customers. Sure, each person might find their $25 lunch has been picked up by a mysterious benefactor. That customer might be a multimillionaire.

And even if your gesture doesn't have a big financial impact on each customer, I'm sure the small act of kindness would be gratefully received by each customer you comp on that day. Again, be prepared that they may spread the word about the $0 meals. Good news travels fast.

You could arguably make a bigger impact by matching the day's receipts and giving that money to the employees, even those who were not working on that particular day (as long as management doesn't pocket it). There are just so many ways to peel this onion.

Members of the Moneyist Facebook Group also suggest remembering the staff in your 24-hour bonanza at these two establishments. One woman writes: "I like the idea of honoring the staff. If you were to pick up my $100 tab, I'd like it, sure."

You could, arguably, make a bigger impact by matching the day's receipts and giving that money to the employees.

"But if each staff member got $100," she adds, "that money would go directly to the people who made these spots special. It would go to buy school supplies, pay a light bill, or fund dinner out for someone who might otherwise not afford it."

Another Moneyist Facebook Group (META) member said that she did something similar to what you are planning. "I did this at a Chick-fil-A in Santa Rosa after fires burned down part of the town some years ago. I didn't prearrange it so that might make a difference."

"I had collected money from friends so it wasn't all me. Anyways, Chick-fil-A needed to use my physical credit card to ring up each individual order. The manager would periodically check with me to see if the total was okay. I believe I did have to switch credit cards after a while."

"People were so grateful as everyone in the area was so stressed out," she adds. "I actually sat with a group who were dining in and we chatted for a while. What you want to do is great but if you think so highly of the staff, maybe you should do something for them, too."

Whatever you decide, your husband would be proud.

More columns from Quentin Fottrell:

'Poverty doesn't have to be my reality': I thought I'd have to rely on Social Security. Then I taught myself how to invest.

'I feel tricked': My contractor handed my $42,000 pool upgrade to a subcontractor I had already rejected. What can I do?

My 87-year-old mother wants to pay for my brother's kids' education. I don't have children. How is that fair?

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-Quentin Fottrell