To Give or to Judge: The Ice Cream Thief and the Gas Station Smoker

"If you want God to hear your prayers, hear the voice of the poor.   If you wish God to anticipate your wants, provide those of the needy without waiting for them to ask you." – St. Thomas of Villanova

I was recently at a gas station when a homeless man approached me and asked for money. Since my pockets were empty, I offered a compromise: I was heading inside to pay for my gas with a card, and I'd be happy to buy him something to eat. His response caught me off guard. He didn’t want food; he wanted a pack of cigarettes.

As the pump ticked away, his request weighed on me. Was this really how I wanted to help? Would buying them mean I was just enabling his addiction? In the end, I went inside, paid for my gas, and skipped the cigarettes. I braced myself for an angry confrontation on the way out, but when I stepped back onto the pavement, he was already distracted, deep in conversation with someone else. He didn’t even notice me leave—but the ethical dilemma stayed with me.

Coincidentally, my Bible study class had a heated discussion about this exact topic just last week. One person argued that withholding cash is the more responsible choice, reasoning that we shouldn’t fund someone’s self-destruction if they use the money for harmful, addictive substances.

Another person pointed out that living on the street is a grueling, exhausting reality. They noted that the homeless today are much like the lepers of Jesus’s time—marginalized, feared, and shunned by society. If we are called to show them the same radical love and mercy, then any gift we choose to give should be offered freely, without strings attached. If a pack of cigarettes provides a brief moment of comfort in a brutal day, who are we to micromanage that choice? Judging someone’s worthiness assumes we know their story, their pain, or what they need to survive the next hour better than they do.

The problem is, our theology often collides with our history; we make decisions based on past experiences. Last year, while visiting family in New York, my husband and I stopped at an ice cream parlor. As we walked out, a homeless woman approached us and asked if we would buy her a milkshake. It seemed like a harmless, simple request, so we turned right around and ordered it for her. But as the employee was blending the shake, the woman suddenly bolted into the store, yanked open the retail freezer, grabbed three large tubs of ice cream, and ran out the door.

My husband and I just stared at each other, completely perplexed. "She just stole ice cream right in front of us," we muttered. Technically, we could have walked away without paying for the shake, but that felt like stooping to the same level. So, we paid for the shake and walked out into the city. The thief was long gone. We tried to find another homeless person to give the shake to, but came up empty. Since we already had our own ice cream, we ultimately had to throw the extra shake in the trash. The whole experience left a sour taste in our mouths—and very little desire to help anyone else.

Generally, I still believe it’s better to offer structured support—like donating to shelters or food banks—rather than risk feeding a cycle of addiction. But logic is a luxury of time, and most of the time, we only have a split second to decide. In my town, most encounters happen at busy intersections. A person approaches my car window, the light is about to turn green, and I'm forced to make a choice: Do I hand them a dollar from my wallet, or do I take the time to drive to a fast food restaurant, buy a meal, and try to find them again?

During our class, someone shared a practical compromise: she keeps low-denomination fast-food gift cards in her glove box so she always has something useful to hand out. I think that is a wonderful, tangible idea.

Ultimately, it isn't our responsibility to micromanage how someone else uses the mercy we extend. We do, however, have a clear moral obligation to help those in need. Jesus instructs us: “When you hold a banquet, invite the poor, the crippled, the lame, the blind; blessed indeed will you be because of their inability to repay you. For you will be repaid at the resurrection of the righteous” (Luke 14:13-14).

When we choose to give, the grace we receive in the act of giving is far greater than whatever they choose to do with the gift.

Copyright © 2026 Christy Romero. All rights reserved. If you thought of someone while reading this, bless them by sharing it with them.