How skeptical should you be before giving money to a stranger?
A reader we’re calling Diletta recounted a 30-year-old memory when she emailed me recently. Back in 1995, Diletta recalled, she lived about 100 miles south of Chicago.
One day she drove her teenage daughter and several of her friends into Chicago for lunch, shopping and theater. Diletta failed to notice that a woman on the street approached one of her daughter’s friends and proceeded to tell her about her 6-year-old daughter who needed surgery, among other challenges the woman faced. “This kind-hearted girl gave the woman every penny she had,” wrote Diletta. “That meant no money for lunch, theater ticket any souvenir.”
Diletta didn’t realize what had happened until she saw the young woman sitting at the lunch table with just a glass of water.
“She had also been crying over the plight of ‘this poor woman.’”
Diletta bought the girl lunch and paid for her theater ticket since she didn’t want to leave her out.
She also recalled “gently trying” to tell the girl that the woman’s story was probably not true. “Illinois had Medicaid coverage for children if indeed she had a daughter, and she would not need to be begging on the corners for surgery money.” While she believed it likely, she did not tell the girl that the money would likely go to drugs or alcohol.
“What advice would you give to help kids understand that it’s great to have a heart for people in need, but not to get suckered into handing your money over in situations like this?” asked Diletta. “What can be said to make young people aware without completely jading them?”
As I've written before, none of us can really know and shouldn’t expect to know the true reason someone asks us for money, nor how they plan to use any money we may provide. The right thing, when someone asks for money, is to decide whether or not to give it, based on whatever criteria you may see fit: whether the person looks truly needy, when and where the approach is made, what your financial situation may be at the moment, whether the pitch sounds sincere, original or even amusing ... all of these are legitimate considerations, if you choose.
You should not, however, have any expectation that you can control how that person spends whatever money you may give. Once you give someone your money, it's their money, and he can spend it any way he likes.
Not to give money is an entirely acceptable decision, ethically speaking -- asking you for money in no way creates an ethical obligation for you to give it.
It also shouldn’t be expected that someone would give away everything. I’m reminded of Joseph Singer’s book The Edges of the Field. The title is drawn from an Old Testament passage in Leviticus that instructs property owners not to reap the very edges of the fields they own nor to gather fallen grapes from their vineyards, but instead to leave those for the poor. Possession of a resource, according to Singer, implies an obligation to a larger community.
That notion might have been helpful to Diletta in explaining how it’s the right thing to want to help, but perhaps to consider doing so in a way that doesn’t prove harmful to ourselves.
Jeffrey L. Seglin, author of The Simple Art of Business Etiquette: How to Rise to the Top by Playing Nice, is a senior lecturer in public policy and director of the communications program at Harvard's Kennedy School. He is also the administrator of www.jeffreyseglin.com, a blog focused on ethical issues.
Do you have ethical questions that you need to have answered? Send them to jeffreyseglin@gmail.com.
Follow him on Twitter @jseglin.
(c) 2025 JEFFREY L. SEGLIN. Distributed by TRIBUNE CONTENT AGENCY, LLC.
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