“I’m Not Going to Rob You”



Kyle and I stepped out of a popular new burger joint on Friday evening after a nice date, checking to see if the rain had resumed while we ate.




Realizing someone must be addressing Kyle on the otherwise deserted street, we turned around to see the speaker standing a few yards down the sidewalk from the entrance to the restaurant.  He was a tall man in his 30s with both his hands stuffed in his sweatshirt.


hand outSpeaking in a loud, monotone voice with unfocused eyes, he announced, “I’m not going to rob you.  I just need some money to get home.  I’m out on parole now.  I need $17 but I’ll take whatever you can give me.”


Slightly taken aback by his icebreaker but not wanting to refuse to help him, Kyle pulled out his wallet, saying, “Let me see what I have…”


Immediately the distance between the man and us disappeared and he was very close to Kyle, saying that he appreciated the help getting home.  I was standing behind Kyle’s back.  I knew Kyle was looking for a five dollar bill, which is the amount we had previously agreed to give to people who ask on the street.  It took Kyle a few moments to ascertain that he didn’t have any fives, during which time the man got a good, close look at the contents of Kyle’s wallet, despite Kyle trying to hold it at a concealing angle.


When Kyle pulled out two one dollar bills and handed them to the man, the man became agitated and raised his voice.  “I need $17 to get home, man!  I can see you have a twenty right there, why can’t you give me that?!”  Kyle tried to rebuff him, saying “This is what I can give you” but the man became more insistent and reached toward Kyle’s wallet to better examine the contents of the billfold.  This all happened very quickly and with much volume and agitation.


The man didn’t seem to be taking “no” for an answer, so I leaned in to put my hand over the opening to Kyle’s wallet, loudly saying “Good luck to you, sir.”  The man went one more round with Kyle verbally – he said “You take the two dollars and I’ll take the twenty” and Kyle said “This is all I can spare right now” – before giving up and perfunctorily thanking us.  We quickly turned and walked toward our car.  We didn’t speak to one another for a few blocks, hoping we weren’t being followed.


The whole exchange took just over a minute so there wasn’t much time to process what was happening in the moment.  I didn’t feel particularly unsafe because we were standing directly in the light cast by the bustling restaurant we had just exited and I didn’t think he would try to mug us with so many people just a few feet away.  But after we were away from the man’s presence, we realized he had never taken his left hand out of his sweatshirt and we felt more unsettled.  The man clearly wasn’t all there mentally so he easily might have acted irrationally.


The whole incident left us troubled.  Kyle really didn’t like how we handled it.  He wished that we had asked the man’s name and talked with him and perhaps bought him some food.  I thought we did as well as we could, given how aggressive the man was and how quickly the situation escalated.  In my opinion, the man was really doing the whole homeless community in our city a disservice with his behavior.  It made us feel much more reluctant to open our wallets to someone who asks in the first place, for fear of being harassed for more money than we are willing to give.


Lately, we have tried to be intentional about giving small amounts of money to people who ask and most of the time it’s a neutral or feel-good experience.  We recently gave money and bought some food for one particular man who we encountered and spoke with on a few occasions.  He also tried to upsell us, so to speak – when we brought him the food we purchased for him, he asked for money a few times in rapid succession, but we just cheerfully told him no and he seemed dejected but didn’t argue.  We walked away from that interaction feeling like we did help him in a small way, and now we know his name and a bit about his life and can recognize him around town.  It was a humanizing experience, from our point of view – unlike this one from Friday.


Yesterday, we made a $50 donation to the local homeless shelter that we give to once or twice a year (we volunteer occasionally at a different homeless shelter/soup kitchen).  This isn’t the first time we’ve made a donation in response to an unsatisfying interaction with a homeless person.  We hold the opinion that our money better helps the homeless when given through a shelter or other organization, though we sort of hedge our bet by also giving nominal amounts of cash directly to people who ask.  People definitely come to different conclusions on this issue, but that’s where we are.


Our perception of this experience had nothing to do with the money involved.  We obviously could have given this man $2 or $20 or $50 without it harming us in the least.  But it seemed like he thought he had the right to whatever cash we had, which was a real turnoff.  Not that the money is ours, either, but we have been appointed stewards of it so (I think) we can’t let ourselves be pushed around.


Have you ever had an unsettling interaction with a person asking for money (stranger, family member, or friend)?  Have you ever been mugged or robbed?  In what manner do you care for the homeless or poor in your city?


photo from Free Digital Photos


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39 Responses to "“I’m Not Going to Rob You”"

  1. That sounds like an unsettling experience. I’m glad you guys are OK. Have you read The Gift of Fear? One of the red flags the book talked about is the “unsolicited promise” – i.e. “I’m not going to hurt you” – means that the promise will be broken.

    When I decide to give money on the street, I will either have $1 or $2 ready in my pocket to take out, or I will tell them that I can buy them a sandwich, if they’d like. Like you, I hate taking out my wallet because that just opens up another point of vulnerability.
    Well Heeled Blog recently posted..Having More Dates (and my thoughts on a long distance marriage)

    1. Emily says:

      I can definitely see that point. It was very weird that he led with that “promise,” especially with his mannerisms. But in the end he kept it!

  2. NZ Muse says:

    Wow, that sounds scary. And very rude and entitled of him.

    I never carry cash, so I guess even if I lived in a country where this was more common I wouldn’t really face this.

    Opening up your wallet is definitely risky. I remember doing so in Cambodia and that resulted in me getting ripped off and later realising it (she woman saw how much cash I had).
    NZ Muse recently posted..Women’s Money Week: Career progression and climbing the ladder

    1. Emily says:

      I don’t care to carry cash either, but Kyle likes to – a bit, anyway. Was your money taken at the time you opened your waller or later on?

  3. I regularly purchase a street newspaper in Nashville called “The Contributor.” The paper covers issues of homelessness and poverty while providing homeless vendors a source of income. I prefer to do this than just hand someone cash.
    Addison @ Cashville Skyline recently posted..The High Costs of Staying

    1. Emily says:

      We bought one of those once in Chicago. I’d never heard of it before but it makes a lot of sense.

  4. Very scary incident to say the least. I’m all for being a Good Samaritan but situations like this are why I quit interacting with people on the streets who ask for money. That began in college when I was approached almost everyday when I went into downtown Atlanta. You simply don’t know what it’s going to evolve into (especially if they are belligerent)and I’m not willing to take that risk. I can give in other ways to help these people (like donating to the homeless shelter). I’m sure this sounds a bit heartless, it’s just where I’m at right now on the issue.
    Brian @ Luke1428 recently posted..How Landlords Can Screen Out A Potential Problem Tenant

    1. Emily says:

      We don’t encounter the homeless on a daily basis here. I got used to passing by homeless people growing up in the DC area but Kyle isn’t so callous. I don’t blame you for where you’re at on the issue now. We all have to listen to our consciences.

  5. moneystepper says:

    I think that the best approach is to never give money to people directly in the street. Research has shown that this only encourages any behaviors that led them there in the first place. To really help (as you point out), it is better to give the money to the organised charities who understand how to really help people.
    moneystepper recently posted..Investing my ISA allowance. Should I invest it all at once?

    1. Emily says:

      I’m sure there is empirical research on the matter but I haven’t read it. Do you have any references?

    2. Katherine says:

      My church had a sermon series on charity and generosity last month, and one of the things the ministers stressed is that it shouldn’t matter whether the person asking for money is lying, or using the money to buy alcohol or cigarettes or whatever. Trusting that they need the money gives the asker a bit of dignity (to spend the money on whatever they feel they need, not to have the privileged people on high tell them what they need) and is a good spiritual practice for the giver.

      That said, we should also absolutely give to organizations that work against homelessness and poverty, and not put ourselves/let ourselves be dragged into a dangerous or threatening situation.

      I live in a city where it is pretty common to see people begging at major intersections. My husband and I have talked about keeping dollar coins in the cup holders of our cars, so that we can give in these situations without having to dig through our wallets. (This is something that my father-in-law practices.)

      1. Emily says:

        Kyle and I agree with your position a bit which is why we choose both strategies. For example, Cash Rebel summarized a recent This American Life podcast on how effective it is to just give poor people money vs. going through NGOs. Not sure how the exercise translates from 3rd world poor to 1st world poor, though.

  6. I never carry cash, and I think I’ve had the same sort of experience Brian has had, living in Atlanta – I just don’t engage anymore because some people get belligerent or will follow you. I simply don’t want to put myself in that situation, so if someone approaches while I’m out, I usually just say, “I don’t have any cash on me, I’m sorry,” and keep moving.
    Kali @ CommonSenseMillennial recently posted..3 Sneaky Ways to Save During College

    1. Emily says:

      It sounds like Atlanta has a very different (and larger) homeless community than Durham does. I don’t care to carry cash, personally, but part of the reason Kyle wants to is to give to people on the street.

  7. I very rarely carry cash, and so I think a lot of people who ask me for money think I am lying to them (whether they’re asking me to buy a raffle ticket, or are homeless asking for a bit of spare change).

    I recently parked outside a gas station when D ran into to grab something, and a man approached the car asking for bus money. This time I actually did have a twonie on me, so I figured I could spare it. But to get to the coin I had to go through my entire wallet. I tried to keep it as central to the middle of the car as possible (farther away from the window) but it felt like he was waiting to grab it. Thankfully D came back (gotta love that he looks intimidating to anyone who doesn’t know him – buzzed hair, a bit husky, and tall) and then the man left. Without the $2.
    Alicia @ Financial Diffraction recently posted..A Safety Net On Doing My First Income Tax Return.

    1. Emily says:

      It’s easier to say “I don’t have any cash” than “I don’t want to give you any money” even if both are true. :/

      I would be very nervous being approaching in a car because you’re a bit trapped! And there is the possibility for carjacking/kidnapping.

  8. Eric says:

    I have given money to needy people before, but I agree that I would rather give through an organization than to someone directly.

    On the occasional, rare encounter when someone has been pushy or intimidating, I always decided against giving them anything at all. And I never, ever take out my wallet. If I have ever given anything, it has been change loose in my pocket (have to be careful with that abroad where a coin can be worth more than $2.)
    Eric recently posted..How to Get a Bank Fee Refund

    1. Emily says:

      I didn’t really think we could change our minds and say no to giving this man anything after we engaged with him, but we have turned people down from the get-go before. Have you ever changed your mind mid-give?

  9. Money Beagle says:

    That’s pretty scary, I would have to admit. I think I would have ended it once he started getting too close. One time my wife and I were leaving a restaurant in a strip mall in a pretty suburban area and we were approached by someone, and she was pretty pushy trying to “get money to get home”. My wife and I basically said “No” and went on our way.
    Money Beagle recently posted..Urgent Care or Emergency Room: 6 Ways To Decide Which Is Best?

    1. Emily says:

      If he got so upset by being offered $2 I’m not sure how he would have reacted if we decided not to give him anything. There really just wasn’t time for us to process. 🙁 I’m much more comfortable saying no than Kyle is – maybe it shows on my face because he gets approached more than I do!

  10. SarahN says:

    I appreciate you sharing this!

    My experiences and responses vary. I was surprised that you (as a couple) have a set an amount to give when requested, that’s smart and something I’d never considered. Something I could implement even myself.

    I lived in a very poor area, with a lot of public housing. People ask for money a lot, and generally speaking I don’t contribute. They are all locals, and so it can start an unhappy relationship that endures. That being said, I have people who repeatedly ask (even at the same time once a week) and have no recollection of me!! That being said, once a man said to me on my way to the grocery store ‘I need money for food’. When he mentioned it again on my way back towards home and the green grocer, I took him on his word. In the green grocer, I said to him, “sure, pick any food you want” (and honestly, he could have bought one of everything and I’d have been happy!) but he was perplexed. Strawberries were closest, so he selected those. At this point, I was in line to check out, and the store owner hollered from him to stop bothering her customers and get out. It escalated with some guy coming from the back room and walking him outside. The discussion was rather heated. I bought my stuff and the strawberries, and handed them to him on the way out. Later that day, the store owner said to me, when I was back there, how were your strawberries? (Seeing we had different perspectives on the guy), and I stood up for what I did and said, ‘I’d rather give food than money, I’m sorry you thought he was bothering me’.

    That being said, I AM reluctant to give cash, for the fictitious (ie in my head) situation you has happen to you. I will give money to Big Issue sellers (a magazine where the seller gets half the ticket price and are often homeless or marginalised). I no longer enjoy the magazine, but I encourage them selling it, as it’s a supported network.

    Overall, I think my general reticence to give money may explain why I volunteer at 3 organisations – no all poor relief, but I actively volunteer at church, state emergency services, and a food co-op, and two from three of those are weekly. To me, it’s easier to give my time, than money. Whilst I sometimes feel overwhelmed by my community commitments, it’s a non negotiable part of who I am.
    SarahN recently posted..Review of my six weeks in management

    1. Emily says:

      Kyle and I have actually had many discussions about how to respond to the homeless in our city. Our optimal solution is to give $5 gift cards to a grocery or drug store, but we haven’t implemented that yet. We actually met the man we bought food for while he was loitering at the entrance to a store, and then a couple weeks later I saw him being asked to leave the entrance to another store. I applaud you for buying some groceries for the man you encountered but I also understand the store’s position of not wanting them to make a habit of being at the store because I’m sure it does bother some people. The good thing about giving your time is that you have a good understanding of the benefit you’re generating, although sometimes with volunteering I feel rather superfluous and I think they could be doing more with straight up money. :/

      1. SarahN says:

        I just wanted to let you know this post generated me reflecting on my giving… I linked back to you.
        SarahN recently posted..Giving – time and/or money

        1. Emily says:

          Thanks for letting me know! I read it this morning.

  11. Mrs. PoP says:

    I think you guys handled it the best you could, and Kyle shouldn’t beat himself up over it. In general, I often try to disengage from the aggressive requestors and remove myself from the situation, especially if I am alone. But when the homeless person approaches me as a person and not as an ATM, I am a lot more likely to open my wallet for whatever couple of dollars might happen to be there. Honestly, this happens a lot more when I’m traveling than at home and do happen to have cash on me since I like cash when I travel.

    And actually, thinking about it, at FinCon this kindof happened on the last night. The homeless guy wasn’t aggressive, actually he had helped a group of us with directions, and I gave him $5. He looked in my wallet as I was pulling out the $5 and saw the $20 and said that would really help him out. But when I told him I needed that to get to the airport the next morning, he didn’t push it and graciously accepted the $5. But it was a bit uncomfortable when he looked in my wallet. =(
    Mrs. PoP recently posted..Breaking Up Is Hard To Do…

    1. Emily says:

      I’m fairly disinclined to give money when I travel, though Kyle wants to respond whereever we are. I feel that the homeless in Durham are much more my responsibility than the homeless in other cities!

      Yes, I think it makes a big difference to engage one another as people. But I also get that they probably want to give a lot of quick pitches because there is probably a low “yes” rate. Maybe that man was asking every person who came out of that restaurant.

  12. I’m so glad that interaction didn’t get any worse than it did, Emily. As others have said, neither Kyle nor you need to feel bad in any way for how that went down. You just ran into someone who wasn’t totally all there, and also in some real need. Nothing you could’ve done would have really resulted in a great outcome. Even giving the $20 would have left you feeling manipulated or bullied.

    God bless you guys for giving to that charity in response to that interaction, too.
    Done by Forty recently posted..Rashard Mendenhall is My Hero

    1. Emily says:

      Like I said, I didn’t think he would really do anything desperate since we were right by the restaurant. You are right that there was no really good outcome since what he wanted was more than what we were willing to give.

  13. saverspender says:

    That is really unsettling but I can also see how he might be annoyed that you had the money and wouldn’t give it.. that said, I’m glad it didn’t get worse. It can be scary when you aren’t sure about the outcome, especially if you’re noting that his eyes were glazed, and his left hand never left his jacket.
    saverspender recently posted..Where do the richest people in the world live?

    1. Emily says:

      Well, he chose to look in the wallet. We weren’t trying to flaunt our cash (though I like the strategy others suggested of keeping smaller bills in our pockets). He was trying to see if pushing for more money might be fruitful. If he hadn’t looked he wouldn’t have been annoyed. 🙂

  14. […] from Live to List used my post “I’m Not Going to Rob You” as a jumping-off point to discuss giving time vs. giving […]

  15. […] you might have a student loan to contend with, or you might find yourself in the middle of an unsettling encounter with a stranger demanding money ala Emily from Evolving Personal […]

  16. I just ignore those folks. The less interaction you have with them, the better it is.

    There is a reason they are homeless.
    No Nonsense Landlord recently posted..A Day in the Life … Apartment Turn

    1. Emily says:

      No, we won’t ignore them. Every person has dignity. But we are trying to find the best way to help.

  17. Mik says:

    too many of these panhandles are dishonest which is why I only give $$$ to respected charities !!!!

  18. […] Emily presents “I’m Not Going to Rob You” posted at Evolving Personal Finance, saying, “My husband and I had a disturbing interaction with a homeless person last week, which caused us to think about how we care for the poor in our city.” […]

  19. Siobhan says:

    I know I’m late to the game, but I wanted to mention: we live on a military installation and right around the post in the neighboring towns, there are a lot of homeless/unemployed veterans. We are approached constantly by elderly vets (there are also a few who pose as vets for sympathy, which disgusts me) and some things I’ve come to notice are:

    – men are very unlikely to approach me for money when I am by myself or with my 3-year-old son
    – men are a lot more likely to approach my husband when he is by himself
    – men are inifinitly more likely to approach my husband when he is with me, regardless of whether our son is with us
    – women are likely to approach both of us when we are alone, but more likely to approach me versus my husband when we are together

    Growing up in a major city (Philadelphia), I was taught that men often approach other men for money when they are with a woman, the assumption being that the man will be more likely to give money, and give more money, to show his date/partner that he is caring and charitable. Women don’t discriminate, but will approach the woman if she is with a man, either because of gender sympathy or because women tend to be more “nurturing” and will give more.

    My husband is a bit overprotective – being in the Army tends to have that effect, lol – and we had a discussion about how to handle requests for money when we were in college, since our campus was in Camden, NJ. He prefers that I do not ever give money when I am alone, that I either offer to help them find a shelter/center or just decline and walk away if I feel unsafe. When we are together, he will give money (although not to those who we know are falsely posing as vets) but never more than $7, which is enough to buy a large meal from a fast food joint or a pack of cigarettes in our area. He keeps singles in his pocket separate from his wallet, so he never has to open or show his wallet to do so. I very rarely carry cash anyway, so I typically have no issue with declining.

    We volunteer as a community kitchen-slash-shelter, this past Easter is actually the first time we brought our son to introduce him to the idea of volunteering. I feel this helps far more in the long run than a few dollars, so I try not to feel guilty about declining to give money when I’m alone. But I do sometimes fear for my personal safety, and the situation you two were in probably would have caused me to panic, so it’s probably better for both the asker and me this way.

    As an aside, a friend of ours used to work in an office on a popular street in the city, and every morning would pass a man asking for change on the corner of the sidewalk. He started buying an extra cup of coffee and a breakfast sandwich each morning for the man, a practice he continued for more than two years. It wasn’t until he came into the office late one morning that he saw the man pull off his ratty sweatshirt and climb into a brand-new BMW, that he realized this was literally the guy’s job. I try not to let that affect how I approach giving and charity, but I admit, I often think of that man when someone asks me for money.

    1. Emily says:

      Thanks for sharing your observation and system! You have obviously had many experiences with the homeless that have informed your strategy and I appreciate hearing about it. I hadn’t thought before about the differences between men and women askers and potential givers.

  20. […] read a very interesting post this morning by Emily at Emerging Personal Finance called ‘I’m not going to rob you‘ (you can read my comment too).  It spoke to me as last night, I reflected on my […]

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