Second-Guessing Generosity

To Give or Not to Give

One day last week during my lunch break, I packed our little girl in the car and set out to purchase an activity jumper for her. “Are you ready to go on an adventure?” I said in an overly excited voice I save just for her as I buckled her into her carseat. I call every outing with our girl an adventure as a way to pep both her and me up before each outing. I never know what mood she’ll decide to embrace as she stares rear-facing at the beige backseat of our car in solitude. When I describe it that way, I’m surprised she doesn’t cry more while confined to the back of the car.

On our way, we made a short detour to Walmart so I could get cash out and grab a few essentials such as eggs, lettuce… and Mike and Ike’s — it’d been a long week and chewy candy is my Ben & Jerry’s. At the register, I got some extra cash out to avoid future situations of having no cash on hand. And then Baby Girl and I were in the car again, driving to meet someone named Lauren from Craigslist, the seller of the activity jumper.

As we pulled up to the stop sign to leave the Walmart parking lot, I noticed a man with his wife and two young children. The man’s wife was sitting in the grass with a toddler by her side and an infant in a stroller. The man stood with a sign that read Have Two Children. Need Work. Need Food. Need… I didn’t have a chance to read the rest of the sign because I was at the stop sign. And I needed to turn right. So I rolled down my window and hastily fumbled in my wallet, which was full of $20’s and only $20’s. So I handed the man a $20, to which he replied “Thank you. God bless you.” as I wordlessly rolled up the window and sped away.

Initially, I felt tears at the corners of my eyes as I thought, Those poor children. That poor family. But I had a 20-minute drive ahead of me, and as my emotions cleared, my thoughts began evolving. What were you thinking? How do you even know they needed that money? If they were at Walmart, they obviously drove there in a car. And they had materials to make a sign. I started feeling sick to my stomach. And then I began to assume the worst. What if that whole scene was just that guy’s day job? He just goes to a different locations each day and brings his family along for extra sympathy. And you got duped. You fell for the ruse and gave them $20! You didn’t have a $5, and so you gave them a $20?? The same $20 you have to stretch over an entire month for your own personal spending? Great job. 

Living in New York City made me less than trusting of people asking for money. I saw the same people day after day on the subway telling elaborate stories of their misfortunes and then going around from person to person asking for money. They were professional peddlers. And for people who had never heard their speech (aka all the tourists), it was easy money. I used to give them money until I saw the same people on different corners each and every day. Or on different trains. I had people approach me individually with detailed tales of why I needed to give them cash. And after a few months of being surrounded by these antics, I turned off my emotions and just ignored it all. When we moved to Boston, it was the same: a large homeless population finding creative ways to get cash from the general public. I knew I’d become desensitized and hardened, and I didn’t like it. But after a few times of offering a few peddlers food instead of cash and being turned down, I didn’t feel so bad.

Why didn’t I offer that family a hot meal? Had I learned nothing from living in big cities? I felt dumb. Really dumb. I decided I wouldn’t tell Johnny what I’d done.

My thoughts were interrupted when we arrived at our destination. The Craigslist purchase went swimmingly. The jumper looked brand new, Lauren was extremely normal and not creepy, and I was very pleased with the whole encounter as I began the drive home. Baby Girl’s cries erupted from the backseat, her cue to me that she was ready for her lunch break. And my mind wandered back to earlier, my impulsive moment of generosity. And I decided I was okay with what I’d done. Maybe the guy was a professional peddler. So what. The money was for his children. They shouldn’t have to suffer. And maybe he and his family did need the money. Who am I to guess what they’re actually going through in life? Baby Girl and I drove past the corner where the little family had been standing just 40 minutes earlier. They were no longer there, and no trace of them remained, as if it had never even happened.

Later, Johnny asked me how the Craigslist purchase had gone.

“Good! Really good. The jumper’s in perfect condition.”


“I gave $20 to a guy and his family.”


And I explained it all.

And Johnny said, “It’s okay. I’m glad you did it. I’m sure they needed the money more than we do.”

And maybe he was glad. Or maybe he was just making me feel better. But either way, it made me feel better. And that’s why I love him. And if I had it to do again, maybe I’d do it just the same.

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  • Reply Brian June 6, 2013 at 7:44 am

    I tend to not give anything other than food to people begging at intersections. There have been too many news stories (around here) about how some of them are making 50-60K a year in cash. So when I do give I tend to give to organizations and homeless outreach programs. There is a lovely mission downtown that we give to a lot and another program that goes out to known “camps” and gives out blankets.

    In the end I feel better about that, but I do feel bad for the people who are legitimately in need who don’t get the help they need because of a few thieves.

    • Reply Johnny June 6, 2013 at 11:32 pm

      That’s probably the worst part of it all. I’m sure I’ve passed by plenty of people who have very legitimate needs, but the career panhandlers do a great job of taking your heart out of most giving situations.

  • Reply Michelle June 6, 2013 at 8:30 am

    This is tough! I would feel the same way as you. It’s always hard giving to beggars as you never know if that is just their day job. The other day I saw a 4 or 5 year old girl begging for money, while her dad just stood back and watched. It was heartbreaking.

    • Reply Johnny June 6, 2013 at 11:33 pm

      Ugh, that’s terrible. It’d take a lot for me to hold back from chewing out that dad. At the end of the day, I don’t know their situation, but I don’t know if there’s ever a right time to exploit your children like that.

  • Reply Jordann @ My Alternate Life June 6, 2013 at 8:46 am

    I know how you feel, I’ve been obviously scammed before and that’s made me resolve not to participate in giving money to pan handlers. I give to charity instead, or offer to buy them food.

    • Reply Johnny June 6, 2013 at 11:40 pm

      We prefer the food/charity method as well. But I’ve definitely “fallen” for convincing panhandlers with stories. I’d like to think their needs were legitimate, but it does no good to speculate. The money’s gone and I probably don’t miss it.

  • Reply Roo // NEON FRESH June 6, 2013 at 9:10 am

    I’m a sucker and I often give. I’ve also been taken advantage of doing that (One time a woman lost her money inside a grocery store. I paid for her groceries. She found her money. Cashier told her she should give it to me since I paid for her groceries. Woman OBVIOUSLY didn’t want to, so I just left.)

    I think it’s better to err on the side of giving… I think you did the right thing. 🙂

    • Reply Jodi T. June 6, 2013 at 9:28 am

      Roo — That’s crazy! That woman should be ashamed of herself >:/

      • Reply Roo // NEON FRESH June 6, 2013 at 9:36 am

        Right? I thought I was helping her out because she seemed so distressed… and it’s not like we were at J. Crew; it was a grocery store. The cashier was so mad at her when she saw that she had no intention of handing over the money.

    • Reply Johnny June 6, 2013 at 11:42 pm

      Woahhhh. That chick is messed up. What a weird situation. “K… Byeeeeeeeee.”

  • Reply Laurie @thefrugalfarmer June 6, 2013 at 9:20 am

    Good for you, Joanna. We used to be involved with a ministry that would buy and bring people in need food simply if they asked. It was frustrating for all of us at the time b/c we could see in many situations that they were taking advantage of the group and using it so that they could spend their money more frivolously, but the leader of the group always said “It’s better that we err on the side of the kids/people having food to eat.” That comment sticks with me to this day.

    • Reply Johnny June 6, 2013 at 11:46 pm

      That’s a great motto. And honestly, those who choose to take advantage of others and lie/cheat their way through life certainly aren’t enjoying life. But in the end, it’s better that one family who really needs help gets it, even if a bunch of bad apples try to spoil the generosity.

  • Reply Jess June 6, 2013 at 9:27 am

    I’ve been there…and now if I am inspired to hand over the cash, I tell myself I am not going to think about the what ifs. IF on the off chance the money was truly needed and made a difference in that day, that moment, then it is worth it and worth the other times it may not have been.

    • Reply Johnny June 6, 2013 at 11:48 pm

      That’s a great way to approach it. That what if game is exhausting anyway. Hope for the best and let it go.

  • Reply Jodi T. June 6, 2013 at 9:34 am

    I’ve always had a soft heart for the (seemingly) less fortunate. I have given money to people at gas stations for gas, bought food for an obviously strung out person at the grocery store, and given change to scary people in parking lots. My husband HATES it. He says I’m going to get kidnapped for being nice. Since having kids, and having them with me 80% of the time, I’ve really had to reign all that in. He’s right about trusting people, and I can’t take chances like that with my kids with me…. (btw it’s obviously different in this case as you were in your locked vehicle.) However, every great once in a blue moon he’ll be with us, someone will approach and he’ll cave. (He’s really a softie inside – he just doesn’t want us knowing it 🙂 )

    • Reply Johnny June 7, 2013 at 12:09 am

      You’re a good soul. And I think you’re smart to rethink your giving ways with kids present. I didn’t even think about what that might tell kids. On the flip side, it’s probably worth telling kids why you’re not giving to them and safe ways of helping those in need. Definitely something this new parent hasn’t even considered yet.

  • Reply Miranda June 6, 2013 at 9:58 am

    I usually don’t think twice about giving a few bucks or whatever spare change I have, despite knowing that they may be scamming people, but I did have a situation that now makes me think twice about how much I’ll hand out. Around Christmas time this year, my husband and I were out for breakfast and at the light on the way home, we saw what appeared to be a homeless couple holding a puppy and a sign that said, “Trying to travel home for holidays. Need food. Need ride.” Because it was Christmas time, I felt bad and gave them a $10. Not a lot of money, but more than I would usually give. Two weeks after Christmas I saw them at the same intersection with the same dog but a different sign. Maybe they did really travel home for the holidays. Maybe they really were in need. It seemed like they were just taking advantage of people’s sympathy for the dog. I don’t know. I hope that they at least bought him/her some food.

    • Reply Johnny June 7, 2013 at 12:17 am

      As we were leaving NYC, there was a surge of panhandlers who started using dogs in our neighborhood to score more cash. After a few weeks, a lot of people started bringing dog food and water for the dog and talked to the “owners” to make sure they were taking good care of it. Always made me sad to see the poor dogs, but given how much money those panhandlers were probably making, hopefully their owners treated them like kings.

  • Reply Karie June 6, 2013 at 10:12 am

    I think it’s better to give to organizations that help the less fortunate. I wouldn’t second guess – you did what your heart told you.
    Once a man asked me for spare change and all I could pull out of my pocket was 45 cents. He gave it back to me and a verbal thrashing. I will sometimes give money to people (busksters) playing musical instruments and occasionally to people sitting with a cup or something but rarely if approached. Just makes me nervous.

    • Reply Johnny June 7, 2013 at 12:23 am

      I really get anxious about the people that approach my car at stoplights. Just creeps me out. I’ll gladly given money to homeless performers who try to entertain with magic tricks or playing an instrument. At least they’re putting in some effort. And as a copywriter, I’ll occasionally give if I see an original, well-written cardboard sign.

  • Reply Emily @ evolvingPF June 6, 2013 at 10:46 am

    I think that the impulse to give is always from God and it’s not for you to worry about what happens to it after you give it.

    That said, we prefer to give money to and volunteer with local homeless shelters, so we don’t feel bad when we choose not to give to someone on the street.

    • Reply Johnny June 7, 2013 at 12:29 am

      Amen. Even with volunteering and donating to legitimate charities, I still feel a little guilty. But it’s nice to know there’s help available for them if they really want it.

  • Reply Grayson @ Debt Roundup June 6, 2013 at 11:02 am

    I don’t give money, but I do give food. I don’t do it much anymore since I have had a few occasions where the peddler threw the food back at me demanding money. It put a sour taste in my mouth.

    • Reply Johnny June 7, 2013 at 12:35 am

      Yeah, that’s not cool. I’d have some choice words for someone who denied food I offered.

  • Reply Kaylyn June 6, 2013 at 11:18 am

    Yep, if they refuse food, you know what they’re after generally. I live in Baltimore City and summertime means the peddlers are out full swing. What has always gotten me is the loss of dignity. I can’t imagine what desperation you have to be in to stand on a street corner begging strangers. So inspired by the story of Jesus healing the leper (he touched him! that didn’t happen), I started shaking their hands and asking their names as I handed over a granola bar. I’m not sure how it makes them feel, but it’s been really humbling to see them as PEOPLE (regardless of their reasons why they are out there) and not either a. terrible people who rip you off or b. a collection box I can feel good about dropping something in.

    • Reply Johnny June 7, 2013 at 1:14 am

      I love this. At the end of the day, regardless of who they might be, they are people. And that’s something always worth remembering. Thanks for that.

  • Reply Chris June 6, 2013 at 11:24 am

    I’m cold-blooded. One time when I was still a smoker I was outside of work with some coworkers before we opened. A guy came up to us and asked for money so he could get home because his mom was sick. I told him to go pawn his fake rolex he had on his wrist and he called me an a**hole. I haven’t met one peddler that I thought was genuinely in need. I also watched Stossel’s report on Freeloaders.

    If you have 40 minutes to kill, check it out. It’s rather sickening.

    • Reply Johnny June 7, 2013 at 1:21 am

      The Stossel bit passed the :90 second that’s-interesting test, so I’m going to watch the rest tomorrow. I can already tell it’s going to make me angry though. My favorite kind of documentary/video.

  • Reply Jake @ Common Cents Wealth June 6, 2013 at 11:27 am

    I have a similar problem when it comes to giving. I always think about how I could’ve used that money and what we could’ve done with it had we not given it away. I feel bad thinking like this, but I can’t help myself. The only way I have found to avoid it is to make a “giving” budget each month, then I know it is not taking away from “our” money for the month. I think you made a good decision, hopefully the man put the money to good use.

    • Reply Joanna June 7, 2013 at 12:33 am

      That’s a great idea. I’d love to implement that into our budget. If I knew I had $20/month to put toward giving to a random person in need, I’d never feel guilty about it. And I’d probably give more. Win-win!

  • Reply Sally G June 6, 2013 at 11:41 am

    I’ve also called outings to wherever “adventures”. Adventures can be anything! Grocery store run, trip to the park, etc! I think it’s a great concept.

    It’s hard to know when to give and when not to. I hope you end up in a place of peace about.

    • Reply Joanna June 7, 2013 at 12:30 am

      Good to know I’m not alone, Sally! Some of the “adventures” we go on are the most boring outings ever, haha, but our baby girl isn’t any the wiser!

  • Reply Tina June 6, 2013 at 11:42 am

    This is tough, and sometimes you just have to go with your gut. One year around Christmas time, a woman standing outside the mall entrance approached me and asked for money. I gave her $5 and didn’t think too much of it. I chose to trust that she was sincere and needed that money. Just recently though I was getting money out of the ATM at night when someone asked me for money. I thought that was extremely creep and felt ambushed, so I quickly drove off.

    • Reply Joanna June 7, 2013 at 12:28 am

      You make a good point, Tina. Every situation is individual. And you just gotta go with what feels right in that moment and not worry about it!

  • Reply Newlyweds ona Budget (@NewlywedsBudget) June 6, 2013 at 12:04 pm

    I don’t normally give money to panhandlers, but every once in a while there will be someone who really pulls my heart strings and I give some money. It’s a rare occasion so I don’t feel guilty (even if I do get duped). I know my aunt and uncle once bought a whole bunch of groceries for this man who said (insert sob story here), and they felt really good about themselves. A year later, they ran into the same man who gave them the same sob story. He didn’t even recognize my aunt and uncle. They felt really duped.

    • Reply Joanna June 7, 2013 at 12:22 am

      I think it’s a good call to just give and not worry about whether you’re getting duped. You’re trying to be generous, and that’s all that matters.

      And that story about your aunt and uncle is messed up! I would have been pretty peeved!

  • Reply Laura June 6, 2013 at 12:28 pm

    I struggle with this too! It’s so hard not to be cynical about why they are begging on the side of the road… sometimes I give, sometimes I don’t. I think the important thing is not to beat yourself up over either decision. I also give a lot to my church and to missionaries and the occasional charity, so I don’t feel bad saying “no” to the person on the side of the road who may or may not really be in need. I also feel like there are shelters and welfare and stuff for people in need, so in a sense we already pay for their well-being (whether or not they partake in that)!

    • Reply Joanna June 7, 2013 at 12:19 am

      Very good points, Laura. It was easier to say “no” when we lived in big cities because I saw shelters and soup kitchens everywhere. But where we live right now, it’s not so black and white. In the future, I think I’ll try to offer food instead of just money.

  • Reply Danny C June 6, 2013 at 12:30 pm

    Awesome topic. I don’t think anyone will have a perfect answer to cover every scenario that pops up. You can definitely see everyone’s answer has been shaped by all the experiences they’ve had with it though. I do always feel guilty when I don’t give just because I figure I’m in a better position than they are whether they’re scamming me or not. The elaborate story telling tends to be a dead giveaway though.

    • Reply Joanna June 7, 2013 at 12:11 am

      Agreed, Danny. I think you have the perfect outlook. It shouldn’t matter what they’re motives are — they’re obviously in need in one way or the other. I’d like to embrace that attitude more.

  • Reply The Norwegian Girl June 6, 2013 at 5:10 pm

    I can totally relate to your story. I live in the Capital, and so I´m quite used to beggars. But there are just some I avoid ever giving money to. There´s a big problem with traveling beggars from eastern Europe (we´re talking human trafficking, child labour, crime), and they also give these “sad stories” ( and many actually pretend to be deaf/mute/whatnot).
    There is however a project for drug addicts/homeless people who are trying to get back to society, which I support with all my heart. Instead of begging, they are selling these great magazines for about $10, and the sellers get half of the earning. This way, they get to work, talk to people, and earn some money. The magazines are really good actually, with good articles concerning life before, during and after drug addiction.

    • Reply Joanna June 7, 2013 at 12:10 am

      It’s hard to know when to give to the homeless… you want to help them, but you don’t want to help enable an addiction. That project sounds really great. I love anything that helps people to better their situation.

  • Reply Sarah June 8, 2013 at 8:41 am

    This is one of my favorite posts from you guys. And you never know the other person’s situation. The only thing you have control over is how you treat them and I think you responded perfectly. Has anyone mentioned Karma? You will always be better off erring on the side of treating your fellow man better than is necessary. Way to go, Joanna.

    • Reply Johnny June 10, 2013 at 12:29 am

      Everyone deserves the benefit of the doubt. Totally agree with you. And Joanna’s always earned the positive karma in our house.

  • Reply Susan K June 8, 2013 at 11:29 pm

    I’m glad you gave what you had. You are responsible for the reaction in your heart; that man is responsible for his own honesty. I agree with the others about giving food or a needed item instead of money, but sometimes that isn’t possible. Use good judgement, but give!

    • Reply Johnny June 10, 2013 at 12:30 am

      “You are responsible for the reaction in your heart; that man is responsible for his own honesty.”

      Perfectly said and worth remembering for future instances.

  • Reply Jennifer @ Money Aches June 9, 2013 at 12:41 am

    Try not to think of it as possibly giving $20 to someone out trying to scam others. Try to think of it that you possibly gave someone $20 whom really needed it. Maybe the fact that you didn’t take that extra moment to think about your gift means you were really suppose to do it this time. Feel good about what you did and know that just because there are a few people out there who are trying to get something for free this man really may have needed the money.

    • Reply Johnny June 10, 2013 at 12:36 am

      I think the fact that it was so impulsive means it was probably right and probably needed by that family. At the very least, it helped put $20 in perspective.

  • Reply J.Mill June 17, 2013 at 5:54 pm

    Good perspective! I live in Chicago and like to carry food/supplies with me. In the winter, it’s nice to hand out hand warmers and granola bars.

    • Reply Johnny June 22, 2013 at 11:41 am

      I always wanted to be better prepared in NYC/Boston with carrying things to give away, so that’s great you’ve been doing that. And hand warmers are a great idea.

  • Reply Jen C. September 25, 2014 at 5:07 pm

    My husband told me a story once about how he declined to give money to a homeless man, but someone nearby gave him some money. Later that day, he saw the same homeless man purchasing liquor, which justified his reasoning to never give money to the homeless again. I support it, and instead we give to causes we support, and donate clothes and food to the local various homeless shelter/Rape Domestic Shelter/Home for Mentally Disabled. It’s kind of an unwritten rule, so I don’t break it, but I also never carry cash on me, which makes it much easier to live by. I can imagine empathy getting the better of me if I did carry cash around.

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