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Around lunchtime today, I’d just emerged from the train on the Red Line from Cambridge to Downtown Crossing in Boston, carrying a backpack with a laptop, a tote bag with a novel and a journal and a handbag when I saw him sitting at that spot usually occupied by a homeless person. He was begging for money by holding out a cup, I was ready. I dropped my right hand to the compartment in my handbag where I kept a tiny red book with $1 bills. A habit I began this year. I was prepared to give $1 a day to any homeless person I see – be they on the street, on the subway train or in the subway tunnel. As I got closer to that person begging for change, I stopped myself. I put my $1 bill back. I kept my gaze on him wondering, was he homeless? Was he really needy?

He was wearing a sport shirt, white pants, a baseball cap, and horn-rimmed glasses.  Everything was clean. Pristine even. People whom I usually give money to in that spot on any given day were lying down with their paper cup – torn and dirty, or in their blanket – also torn and dirty. Sometimes that spot was home to what appeared to be immigrants from a faraway place. Sometimes that spot was home to not just one but two – usually what appeared to be a mother and a child. I never hesitated when I saw that. But today, I felt like this white beggar stole their spot. I thought he might have been an imposter. So I didn’t give him $1.

Now, why am I writing about this? I am writing about it because it is still on my mind and in my heart. Does it matter? Why should I be so scrutinizing? Why am I so stingy? It’s just a dollar! All I have, I believe, are gifts from God. I have often given without fully knowing who actually benefit or how it is used. So why bother to agonize over this today?

I think the answer is I am beating myself up. Generosity or philanthropy is the act of giving without any expectation of a return. In my moment of hesitation and withdrawal of that dollar, I had practiced judgment. I judged him to be unworthy of my generosity, or I saw him as having robbed that spot for someone else needier. I didn’t want to encourage that sort of behavior. I held back. However, I have my regrets.

The fact is I was making a snap judgment. I don’t know his full story. I judged him based on his cleanliness and whiteness, and thus someone unneedy or less needy. Regardless of superficial cleanliness or tidiness, anyone who is sitting on the streets begging and bowing for change in their cup should be given the benefit of a doubt.

I am not saying that I give $1 every time I see someone begging with a cup. I do set a daily budget – a modest $1 a day. And thus I sometimes have carryover to the next day when I don’t see a beggar. Giving that kind of pocket change to people on the ground on a constant and continuous basis helps me stay in touch with ground needs. I want to expand my views and attitudes about who’s deserving and who isn’t. I must admit that when I smell alcohol or drug from someone as they ask for money, I hold back. Yes, I don’t want my money to go to support a habit that may have gotten them where they are. I am assuming that they are needy of money to buy these substances. And I would prefer to focus on those with clear and convincing needs.

How do you decide whom to give when you encounter a stranger? I’d be curious to know.