The Stranger Problem: To Help or Not To Help?

One Sunday, I was heading to the gym from a mall. As I was heading to the car, someone pulls up to me and speaks in an Italian accent, “Excuse me, I am lost. Where is the airport?” So I told him the direction and told him to search it on Google Maps. He then proceeded to park in the empty spot next to where I was standing. He asked if I could help with another problem and opened the passenger door. At this point, I was very hesitant to get in. I mean, getting into a car with a stranger just does not sound street smart.

So I stood outside the car and said, “How can I help?” He then told me a pretty long story about how he’s an Italian citizen who works for Armani, and he came here (Toronto, Canada) for a fashion conference. He showed me his passport and his conference papers. He asked if I know about Armani, and I said, “Oh yeah, I know Emporio Armani,” to which he replied, “That’s the lower-end brand. I work for Giorgio Armani, the high-end brand.”

At this point, I’m thinking, “Why is he telling me all this? Any other stranger would probably be like ‘I have stuff to do man, can I get going?’” But I’ve always been the type of person who will try my best to help others in need, so I decided to be patient and hear him out.

He then waves me into the car and says, “don’t worry, I just want to show you some things.” So I reluctantly go in, keeping the door open and my foot on the edge of the car in case. From the back seat, he pulls out all of these jackets, dresses, shirts, etc. With each item of clothing, he asked me if I knew the brand and asked me to guess how much each item was worth. Basically, I did not know these brands because I’m a poor student who does not have the wealth, nor the interest, to know these luxurious brands and how much they’re worth. He tells me how this Ferrari jacket is worth $10,000 and how that whatever dress is worth whatever thousands of dollars. He even told me why these items were legit and not fake, pointing to some tags or embroidery or some other things I didn’t understand. And I’m just thinking, “Oh my god, where is this going to?”

As he continued his story, he explained that he has a return flight to Italy in a few hours, and he doesn’t have the money to return the rental car at the airport because he gambled away all his money at Niagara Falls over the weekend. He doesn’t want to tell his company this because it’s too embarrassing and bad for his reputation. He said he has money back in Italy, but he can’t access it here. He asked me if I could transfer him $2000 and he’ll transfer me back the money as soon as he gets back to Italy. He would also give me all of the clothes that he showed me, worth thousands of dollars, because he doesn’t need them and he really needs to get back to Italy.

At this point, I was thinking, are you serious? First, I’m obviously a poor young guy dressed in gym clothes, not some rich looking adult. Second, how could you be so irresponsible to have gambled away all your money? Third, if you had picked someone else off the streets who maybe dressed nicer and looks like they cared about luxurious clothing, maybe you would have had better luck.

On the other hand, he did show me his passport and conference papers. He did have an Italian accent, and he actually looks like a fashion model. So I was seriously conflicted about whether or not to believe his story. What happened next basically was me explaining that I’m a poor student with no money, and I asked if there’s any other way I could help him. He asked me to ask my family and friends, to which I’m like uh………no sorry. After a while, it seemed like he gave up with trying to get help from me and said he’ll go look for help elsewhere and left.

Last post, we looked at the goodness-harm quadrant, with particular focus on unintentional harm, which is when you have good intentions but end up causing harm. No one wants to create harm, but a lack of wisdom often results in unintentional harm.

When I think about unintentional harm, I often think about the stranger problem: to help or not to help? After much reflection, I think we should help if

1. The person is actually in need of help and not faking it to get your money

2. The person will use the money for a good purpose

3. You have the capability to help that person without undue burden on yourself

If these three conditions are met, then we are actually doing good and not just hoping. Let’s analyze each condition.

1. Is the stranger being sincere?

Most of the time, you can tell if someone is being sincere or not…if you are truly focused in the present moment. That’s why those who try to take your money catch you off-guard, when you’re in the middle of doing something or going somewhere. They hope to get you with a small request for a little bit of money, and your distracted mind thinks “Well, I really want to get back to what I was doing, but I also want to be a good/nice person, and it’s only a little bit of money, so sure, why not.”

Once, I was heading home from the subway station, and an old couple called me over. I thought it was strange that a random old couple would call me over, but maybe they needed help, so I went over. They told me they traveled from afar to come visit their son, but they don’t have any cash to ride the subway to go visit their son. They asked me for some change to ride the subway.

At first, I was thinking, this doesn’t make any sense. If you traveled from afar, why are you out on the streets and not in the train station? Besides, we’re literally right beside a subway station. If this station wasn’t the stop where your son is at, why did you get out? And why don’t you call your son and ask him to help?

I knew I had no cash, so I pulled out my wallet and showed them I had zero cash because payments are done via cellphone nowadays. I asked them where they need to go. They told me. I said, “How about I call a taxi for you via my cellphone app, and I’ll pay for your trip there.” They walked away.

It was a short encounter, so I did not get to ask many of the questions I had in my head. I really did want to help the couple, especially since they were old. But the fact that I offered to pay for a taxi to get them to their son, and they refused the offer, indicates to me that they were not being sincere when they said they needed money to ride the subway to go see their son.

The concerning thing though, is that if I actually had some change in my wallet, I probably would have given it to them. And that could encourage them to keep doing this to other people, which is encouraging them to lie. When their peers see that they are successful at gaining money through lying, it sets a bad example.

From this, I learned that a technique to test if the stranger is being honest or not is to offer another way for the stranger to accomplish what they need without giving them cash directly. So if they ask you for money to buy a travel ticket, then offer to actually buy that ticket for them (assuming it’s not too expensive for you). In my case, I gave an even better option than buying the subway ticket for them. I offered them a much more comfortable taxi ride for free. If the stranger agrees, then you know for sure what your money was used for. And if they refuse, then you can be fairly certain that they were not honest in what they wanted to use the money for. And dishonesty should not be rewarded.

2. Will the money be used for a good cause?

Once, I was heading home in a subway station when a young teenage-looking boy came up and asked for money. The difference with this situation compared to the previous two is that it’s quite normal for there to be panhandlers inside subway stations, whereas the previous two situations were really quite random.

I saw the boy had been rejected and looked down upon by other commuters eager on their way to get home from a long day of work. When the boy came up to me, I stepped out of the crowd and asked him, “What do you need the money for?” He told me that he’s really hungry and just wants to buy some food.

Conveniently, there was a coffee shop right beside us, so I took him over. As we waited in line, I asked him, “Why don’t you look for a job?” He told me he’s a school drop-out and he’s tried and tried to get a job but nobody would give him an interview. I told him, “Don’t give up. You can do it. Keep trying.” He eventually said okay. I bought him a sandwich and a drink before I left.

The thing with panhandlers is that they usually sit on the ground with a bowl for collecting money and a sign that says what they will use the money for (usually food). The argument against giving them money is that you don’t know what they will use the money for. The fear is that they will use the money for bad things like drugs or cigarettes. That’s why for panhandlers on the streets, I would buy them a muffin or a sandwich once in a while. This way, I know exactly what my money was used for, and doing it once in a while is not putting an undue burden on myself.

Is this good?

As I think more about it, I think it’s a case of unintentional harm. If everyone did what I did, what would be the result? The panhandlers would get enough food from all the people who are just giving them food once in a while. That would result in some panhandlers getting complacent at being an unproductive member of society.

I think the right thing to do is what I did with that teenage boy. We need to actually talk to the panhandler and encourage them to get back up on their feet. I doubt people choose to go homeless. It’s more likely that uncontrollable circumstances happened to them, which resulted in them becoming homeless. When people are at a low, it can mean the world to them if someone tells them “It’s okay, you can get past this.” And if a panhandler already seems complacent, then definitely need others’ encouragement to find a job and solve their problems. If everyone gave panhandlers some food AND encouragement once in a while, it should have much better effect on the panhandlers’ lives.

3. Can you help the person without undue burden on yourself?

It should be very rare for a stranger to ask you for something that’s hard for you to give from a capability standpoint (not willingness). Logically, their chance of success is much lower. That’s why strangers ask for coins, not thousands of dollars.

That’s also why I was so intrigued by the first story with that Italian Armani person. People don’t just ask someone (especially a young boy in gym clothes) for $2000 unless they are desperate. His story seemed so realistic…that’s probably why I stayed there for so long. I wanted to get a fuller picture to understand if he’s lying or not, and to this day, I’m still not sure.

But in hindsight, I realize that sincerity is not the only thing to consider. In fact, it’s more of an emotional consideration, in that we don’t want to be cheated because it feels bad to have been fooled. So let me make an important point here:

We not are testing people’s sincerity (solely) because we don’t want to be fooled and feel like an idiot. We are doing it because we should be promoting others to be honest and not reward dishonesty.

Looking back, I also realized that it’s a good thing I wasn’t rich because if I was rich and $2000 was like pocket change to me, then I might have actually given it to him the same way people give $2 to panhandlers all the time. Back then, I lacked the wisdom to think about the second consideration: if the cause is good or not.

Giving him the money would have promoted a bad cause. He should not have gambled away all his money. I would assume he got drunk to be irrational enough to lose all his money. If so, he should not have gotten so drunk. He should take responsibility for his bad and stupid actions. He should lose reputation to his company because he gambled away company money. He should not be able to get away from his bad actions through giving away merchandise he got at the fashion conference. I lacked the wisdom to see this back then, but fortunately, I was saved by the fact that I simply lacked the ability to help him without causing undue burden on myself. And ultimately, I think that’s why he left.

Putting it all together

Whenever strangers ask me for help, I always tend to think about it for a long time. I think it’s important for us to help people in need, but it’s equally important to be wise in how we help others. So if a stranger ever comes up to you and asks you for help, I suggest you to go through the following thought process.

First, can you even help them? Usually, the answer would be yes. But in that first story, I could have ended the conversation a lot earlier by simply saying I don’t have that much money.

Second, think about the long-term and domino effects of helping them. Are you promoting them to do good or encouraging a bad act or habit or stupidity that led them to their predicament?

Third, can you help them through a method that’s different from just giving them cash? Because if you just give them cash, you cannot be certain what they will use it for. So offer to buy them that ticket (if it’s not too expensive) or to call a taxi for them or to buy them food. If they accept your offer, then you know you what your money was used for. If they refuse, then you can assume they just wanted the money, and their story was just a way to get your money.

Apply what you learned

Let me share with you one more story and ask you what you should do.

Once, I was walking to a mall that was beside a hotel. As I was crossing the hotel front area to get to the mall, a man in what seemed to be a work uniform calls out to me asks for my help. He explains that he came here for a conference with his colleague, who was standing nearby, also in a work uniform. They need to get back to their home city, and they don’t have enough money to buy the train tickets. The tickets for both of them would cost around $200 (they were unsure themselves). They also needed money to get a taxi to head over there since they needed to get back tonight. They asked me for cash or to transfer them money via cellphone, and they would transfer me back the money as soon as they got back. He also gave me his business card to assure me that he’s legit.

I asked them, how the heck do both of you not have enough money? They said they only brought the company card and company cellphones, and something’s wrong over there at the company bank.

I want you to think not just the decision you would make, but what would you actually say to the people to teach them a lesson about what they should do in the future and to minimize any doubts on your end?

Passionate about self-cultivation, happiness, and sharing wisdom.