Charitable Quandary


Five minutes ago I was driving in my car with a disheveled middle-aged woman who asked me for a ride. I initially hesitated when she asked because I knew three things: she would eventually ask for money, she didn’t look healthy, and it was only a losing proposition for me.

I said yes. Not because one of my goals for the year was to “Help a Stranger” (which has only just occurred to me in this moment), but because I feel sometimes that these opportunities are tests of character. She got in my car after putting out her cigarette and placing the surviving half of it in her pocket for later. She told me her car had run out of fuel at her ex-boyfriend’s apartment and she needed a ride back to it. She was unemployed and didn’t always have a place to stay, but was “trying to find something off-the-books.” Eventually, the lady requested “a few dollars,” which shortly thereafter became “eight or nine dollars for gas.” This felt like more than a few dollars to me (despite a $4/gallon price tag at the moment). I offered her $5 to get her started, which I was skeptical would go towards gas anyway.

She continued to tell me her story the entire ride, which probably lasted about 7-8 minutes. I noticed some minor inconsistencies, but didn’t question them because of a slight but nagging concern about what her dirt-colored trenchcoat might conceal. I dropped her off where she requested, gave her a five-dollar bill outside of the car (wasn’t about to take my wallet out with her sitting next to me), and went on my way.

On the return trip, I couldn’t help but think about where that $5 will be going. I also thought about where that $5 would go if it stayed in my pocket. I hesitate to pass judgement on others, and it was for this reason that I took her on as a passenger in the first place. Whether that $5 would buy me an extra beer next weekend, or her a new pack of cigarettes (or worse), it is trivial in the grand scheme of my own life, but perhaps it’s not so trivial in hers. I don’t know where that $5 will go, and I by no means intend to support any counterproductive spending of it, but what I do know is that it probably means a lot more to her than it means to me. It’s for that reason that I feel I made the right decision. Some might consider my choice to be naïve, but I’d like to believe differently.

Have you ever helped a stranger? If you had the chance, would you?


4 responses to “Charitable Quandary

  • Amanda

    I’ve given my brown bag lunch to homeless people in Downtown Miami. I figured food was better than money and at least I could buy something.

  • Teacher Girl

    It’s funny because the teacher/mom figure in me was worried about you the whole time I was reading this. I think what you did was very sweet and something that most people, including myself, probably wouldn’t do. I am more inclined to buy a homeless person coffee or a meal. In any case, doing something nice for someone is always very cool.

  • Deidre

    a woman once asked me for a ride back to her car and I was about to start a road trip going in the opposite direction so I didn’t give it to her, but my friend who was with me was appalled I’d even consider it.

  • Robin @ our semi organic life

    I’ve never done anything like this. I’ve only heard horror stories. A close friend’s story started out like yours – then got much worse. Thankfully nothing terrible happened but we all yelled at her for being so gullible and as a single young female driving strangers around in a bad neighborhood not having more sense!

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