Excuse me. Hello! Excuse me!” I was walking with friends on a New Haven street. We turned to see a man and a woman striding toward us. Both were tall and bone-thin. When they reached us, the woman took a deep breath. They were homeless, she said; they needed money to buy food and pay for their beds at the New Haven homeless shelter, which charged three dollars a night. They didn’t want to beg, so they had bought a roll of paper towels and a bottle of glass cleaner. They would wash our windshield for money, or the windows of our house, or even our glasses.

My friend Curtis gave them five dollars. I had five one-dollar bills in my wallet and one twenty. I also gave them five dollars.

They thanked us profusely; this would be enough money for the entire day, the woman said. They wouldn’t have to approach anyone else. We were on foot some distance from our car and had no windshield handy. “Please let us do something for you,” the woman said. So, since it seemed to matter so much, I handed her my glasses. The man sprayed them with glass cleaner and the woman polished them meticulously.

As we walked away, I overheard the woman saying to the man, “Let’s go get something to eat.” I wished I’d given them everything in my wallet.

I grew up Jewish, and learned about charitable giving in the context of Jewish traditions and attitudes. Charitable giving is central to ethical behavior in Judaism. The word tzedakah, which is usually translated “charity,” is derived from a Hebrew root that means righteousness, justice, or fairness. The central attitude is that food, shelter, and other basic needs are a human right; giving food to the hungry is not doing them a favor but rectifying an injustice by giving them something they should have had in the first place. Also, in Reform Judaism (the branch of Judaism I grew up in), charity and social justice are placed within the larger context of tikkum olam, or the “repair of the world.”

Yet, if there was a single text that drew me to Christianity, it was Christ’s description of the Last Judgment in Matthew 25:

The king will say to those on his right: “Come. You have my father’s blessing! Inherit the kingdom prepared for you from the creation of the world. For I was hungry and you gave me food, I was thirsty and you gave me drink. I was a stranger and you welcomed me, naked and you clothed me. I was ill and you comforted me, in prison and you came to visit me.” Then the just will ask him: “Lord, when did we see you hungry and feed you or see you thirsty and give you drink? When did we welcome you away from home or clothe you in your nakedness? When did we visit you when you were ill or in prison?” The king will answer them: “I assure you, as often as you did it for one of my least brothers, you did it for me.”

I found the personal encounter described in this passage deeply appealing. In Matthew’s Gospel, the act of giving opens the door between the human and God. We are not merely commanded to feed the hungry; we feed Christ himself when we do so.

On the other hand, the next passage of Matthew warns darkly about the consequences of turning away.

Out of my sight, you condemned, into that everlasting fire prepared for the devil and his angels!... As often as you neglected to [help] one of these least ones, you neglected to do it to me.

In Jewish tradition, though charitable giving is strongly encouraged, there is also an underlying acceptance that we’re not going to help everyone who asks. The first-century Rabbi Elazar suggested that we should be grateful to the people who fraudulently ask for alms, because if it weren’t for them (and, thus, for the possibility that we were being asked for alms deceptively), we would sin every time we turned away from a request (Babylonian Talmud, Ketubot 68a). The Jewish philosophy of giving (at least as I learned it growing up) seems more pragmatic to me; the Christian philosophy (as expressed in the Gospels), more challenging. Can these two approaches be reconciled?

Just before Christmas one year, I was running an errand at the pharmacy when I saw a woman standing by the road with a sign asking for money. I couldn’t read the sign, but I could tell that very few people were giving her anything. After a few minutes, I moved some money to a pocket I could reach easily and went close enough that I could see her sign. It said, “Too sick to work. Help give my kids Christmas.”

Too sick to work but not too sick to stand on a cold Minneapolis street for hours panhandling? I gave her two dollars anyway. “God bless you,” she said.

I looked into her eyes and said, “I hope this helps you.” As I walked away, I thought, “I bet she’s a meth addict. I bet she’ll spend it on drugs.” The question of whether to give money to panhandlers came up a few months ago on an online parenting community in which I participate. Most of the responses were from people who wrote that they do not give to people on the street. Some couldn’t afford to; others didn’t trust the recipients to use the money well. They’ll spend it on drugs and alcohol. Most collect far more money than you realize. When someone tells you she’s out of gas and forgot her purse, it’s always a scam. “I almost always give money when asked for it,” I wrote in response. “I live in a community where panhandlers are relatively rare, so I can give money to anyone who asks for it, and it’s not going to break me. I’m sure some of them are scamming me, but I figure that when I die, St. Peter isn’t going to yell at me for the times I gave money to someone who didn’t deserve it. He’s going to give me grief for the times I turned away from someone who really needed help.”

There were at least a few who agreed with me, but I found my own response unsatisfactory. My gift could give someone the opportunity to make a positive change in her life. Or it could allow her to buy a fatal overdose of a favorite chemical. Some cities have aggressively pushed residents to stop giving to panhandlers, calling those who give to them “enablers” and saying that they’re perpetuating the problem. I often feel that giving money is, at best, an ambiguous act—even as I do it anyway.

The question of the undeserving poor is addressed annually by Jon Carroll, a columnist for the San Francisco Chronicle. Each December, he writes a column encouraging people to donate to what he calls the “Untied Way.” He suggests taking two hundred dollars in twenties to an area where you will reliably find people asking for money and giving twenty dollars to each person who asks until you run out. “It is true that some of your recipients may use the money for self-destructive purposes,” he wrote in his essay in 2003. “That is not ideal, but neither was it ideal when you used your money for self-destructive purposes. We’re all just trying to figure it out as we go along, and your fine home or apartment does not place you closer to enlightenment.”

The Jewish tradition acknowledges the issue of the person who asks for help deceptively, and the Talmud offers various pieces of advice on the subject. The medieval Jewish philosopher Maimonides (1135–1204), like several other sages, suggested that if in doubt, immediate needs (such as food) must be met, but if someone is asking for less critical needs (such as clothing), you can first investigate to see if the person is being honest (Hilkhot Matnot Aniyim 7.6). Moreover, the Talmud says that various horrifying curses will fall on those who seek charity fraudulently—anyone who fakes blindness, for example, can expect to be struck blind (Pe’ah 8.9).

Christian texts have remarkably little to say about the merit of charitable recipients. The focus is on the person who gives, and the effect of giving on the giver. Both Mark and Luke tell the story of the widow’s mite. Jesus “saw the rich putting their offerings into the treasury, and also a poor widow putting in two copper coins. At that he said: ‘I assure you, this poor widow has put in more than all the rest. They make contributions out of their surplus, but she from her want has given what she could not afford’” (Luke 21:1–4). According to Mark (12:43), Jesus “called his disciples over” to point out the widow’s generosity; clearly, this was behavior he wanted people to imitate. Yet immediately afterward he told his disciples that the Temple, which the widow had given her money to support, would be torn down. Clearly, it is the act of giving that is important—not the results of the act. Why?

Maybe it’s in part because the more we give, the fewer material possessions we will have to weigh us down on our path to God. Again, both Mark and Luke tell the story of the rich man who approaches Jesus, asking what he needs to do for eternal life. “Go and sell what you have and give to the poor; you will then have treasure in heaven. After that, come and follow me” (Mark 10:21). But the young man left troubled. His possessions were many, and an obstruction. Reading the story, I can see that clearly. My own possessions, on the other hand, seem utterly indispensable to me—from my computer to my toaster oven, I feel that I need these things. Most likely, the rich young man felt exactly the same way. So God demands that we give: the more we give, the less we will be burdened.

We should give, and we should try, when possible, to avoid any sort of repayment. Jesus makes this clear in his advice to his host when he is invited to dinner. “Whenever you give a lunch or dinner, do not invite your friends or brothers or relatives or wealthy neighbors. They might invite you in return and thus repay you. No, when you have a reception, invite beggars and the crippled, the lame and the blind. You should be pleased that they cannot repay you, for you will be repaid in the resurrection of the just” (Luke 14:12–14). Many times in the New Testament we’re told that we will receive a reward either on earth or in heaven. If we are repaid for our generosity, or admired for it, we’ve been rewarded here.

The repayment model turns St. Peter into sort of a cosmic cashier, tallying up each quarter handed out, each check written, in order to allocate heavenly real estate. Surely there’s more to this than the choice between earning an eternal mansion and settling for an eternal bungalow.

Giving has the potential to be transformative; that potential is part of why we’re asked to give. When we help a needy person, we are facing Christ himself. Perhaps when we least wish to give—when the recipient is most undeserving, or when we least have the time, money, or energy to dig into our pocket—maybe that’s when we are closest to the door that would offer us a transcendent encounter with God, if we open it. This is also, of course, a common understanding expressed in the Hebrew Scriptures, where God’s messengers are frequently encountered in “the stranger.”

I had just dropped my older daughter off at an art class when a man approached me. He was neatly though not ostentatiously dressed. He told me that he’d come to Minneapolis from California. He’d been staying at an area homeless shelter while looking for work. Though he never specifically showed them to me, I could see two cards in his hand—a California driver’s license and an ID card issued by Catholic Charities. He needed money—for bus fare, for food, I wasn’t sure. I didn’t care. I had cash to spare that day.

I gave him twenty dollars. “I hope this helps you,” I said. His face lit up. “It will,” he said, fervently, and I believed him.

In the Jewish tradition, certain kinds of charitable giving are considered more meritorious than others. According to Maimonides, giving begrudgingly is the lowest form of charity; the highest is helping someone to become self-reliant. (Even higher, according to some, is offering the steadying hand that helps someone to avoid dependency in the first place.) According to this ranking, it is more meritorious to give when neither party knows the other’s identity than to give face to face. This is to spare the recipient embarrassment. Large charitable organizations are ideal from this perspective, and an excellent way to help the poor. This is not to say that Judaism advocates turning away from needy individuals—it does not. However, helping anonymously is considered preferable.

On a larger level, I agree with this. Organized charities can accomplish things that sympathetic individuals simply can’t, and people who need help should not have to sacrifice privacy and dignity to get it. But on a personal level, I find that this way of giving appeals to me in part because it is easier for me, and allows me to keep needy people in my community at arm’s length. When I mail a check to a food pantry, I don’t have to see the people in my city who are hungry. This makes it easier to imagine that they’re nothing like me. I’m also not confronted with their hardships as I’m making the decision of how much of my money I can spare to help them. Charities allow me to delegate the actual care, not to mention the worrying, to someone else.

Part of what draws me to Matthew’s Gospel is the idea that giving money or a sandwich to a hungry stranger is itself a potentially sacred moment. And if I find myself worrying later about a stranger I met that day, and whether he’s warm and fed, that’s a door I should be opening, not one I should be closing off. Because the human interaction is important. Seattle columnist Dan Savage wrote a book, The Kid, about adopting a baby with his partner. Their son’s birthmother, Melissa, was what Savage calls a “gutter punk”—a homeless-by-choice teenager who spent summers in Seattle, asking people for spare change. As Savage and his partner were getting to know Melissa, they discussed “spare changing” with her. “People who say no don’t piss Melissa off,” Savage writes, “it’s the people who pretend not to hear her as they walk by. ‘That’s when I’m like, “Hello, I exist.” That’s when we’ll follow you down the block.’”

Pope Benedict addresses the issue in Deus caritas est. “We are dealing with human beings, and human beings always need something more than technically proper care. They need humanity. They need heartfelt concern. Those who work for the church’s charitable organizations must be distinguished by the fact that they do not merely meet the needs of the moment, but they dedicate themselves to others with heartfelt concern, enabling them to experience the richness of their humanity.” He is writing specifically about workers for Christian charities, but the same applies, ideally, to everyone who responds to the needy (and most people, regardless of faith, would likely agree with this statement). “The Christian’s program—the program of the Good Samaritan, the program of Jesus—is ‘a heart which sees,’” Benedict writes. “This heart sees where love is needed and acts accordingly.” Dan Savage realized during his conversation with Melissa that she had probably spare-changed him hundreds of times, and yet he didn’t recognize her. Though he always made eye contact with panhandlers while his partner did not, he realized that he didn’t see them any more than his partner did.

In some parts of the world, eyes are traditionally averted to protect another person’s modesty or to save him from humiliation. In our society, we rarely avert our eyes to preserve someone else’s comfort; usually, it’s to preserve our own. Eye contact here is highly symbolic. Like a handshake, it’s a social transaction—one of our most basic acknowledgments of another person’s humanity.

When we encounter a panhandler, there are really two things we are being asked for, both by the panhandler and by God. One is for something that will meet the person’s immediate physical needs—money, food, etc. The other is for acknowledgement of the person’s humanity—eye contact, a kind word. It is Christ himself who is asking for both, and at that moment, as we’re on our way to work, or to catch a bus, or to buy milk, we have an opportunity to encounter Christ.

There are many reasons not to give money; we may not have any to spare. But generally, there’s no reason not to look a person in the face, or to speak kindly. Not that I always do.

"Rupee dinos?" Please give me a rupee? The child was very small. When I arrived in Nepal, I was told by the directors of the off-campus study program not to give money to beggars. I realized fairly quickly that this was poor advice: Nepalis themselves routinely give money to beggars. The “legitimate” beggars were mostly old and, in some cases, clearly mentally ill; they usually had a set route that they would walk every day, begging for tiny sums of money from every shop they passed. I quickly learned to recognize the old beggar woman whose route was near my school. Each store owner would give her a small coin with a smile, and after observing this, I did too.

Child beggars in the tourist district were another matter. Some were runaways; others were sent out by their parents to beg. But many were out without their parents’ knowledge, and their parents would have been as horrified by their children’s begging as any American parent. Nepalis never gave to the beggars in the tourist district, so I didn’t either. When the little girl asked for money, I quickened my step and shook my head.

“Rupee,” she said again and began to run after me.

I had gotten clear of the market square, and climbed on my bike.

“Didi,” she screamed after me as I fled, “bokh lagyo.” Sister—I’m hungry.

A rupee was equal to two U.S. cents, and ten rupees would have bought her a meal.

“The unbreakable bond between love of God and love of neighbor is emphasized,” Pope Benedict writes near the beginning of Deus caritas est. “One is so closely connected to the other that to say that we love God becomes a lie if we are closed to our neighbor or hate him altogether. St. John’s words should rather be interpreted to mean that love of neighbor is a path that leads to the encounter with God, and that closing our eyes to our neighbor also blinds us to God.”

As I have repeatedly approached Catholicism and then backed away again, part of my struggle has been to reconcile Jewish and Catholic approaches to certain issues. Judaism offers a tremendously useful and results-oriented approach to organized charity. Judaism created the idea of a tithe as a guideline for how much to donate to charity, and has a strong focus on protecting the dignity of those who are helped. I like the idea that tzedakah is not a favor to the person that we are helping, but justice—because no one should go hungry, no one should go without medical care, and no one should be homeless.

Yet when faced with a human being who needs something, I find that the Christian approach is tremendously inspiring. By feeding a hungry person, I feed Christ; when a hungry person asks me for help, Christ has sought me out. I am offered a gift: the opportunity to see this encounter as a moment in the presence of God. My gift may have the potential to transform someone’s life, but even if she squanders it, my gift has the potential to transform my life. If I give with a heart that sees.