It was the kid who saw me first, his dark eyes glancing up to meet mine. About seven or eight years old, he nudged his father, who stood facing impassively out into the traffic on Massachusetts Avenue, one arm firmly around his son’s shoulders. With his other hand the father held up a handmade sign: “My son and I are homeless. Please help.”

I’d hurried past them at first, toughened to such requests in the manner of a longtime city dweller. Buffeted by a freezing wind, carrying a heavy bag of groceries, I was anxious to get to the subway and home. But something about the father and son made me stop short only a few feet from the station doors.

Against my better judgment, I yanked my wallet from my purse on the crowded street, balancing my groceries awkwardly as I rifled through the crumpled bills. What should I give them—a twenty? Nope, couldn’t spare it. A five? Didn’t have one. Finally, I pulled out a dollar. It didn’t really seem like enough, but then again, it was better than nothing.

The moment reminded me of the day before, when I’d also found myself weighing out the value of each dollar in my wallet. After a day of holiday shopping with my boyfriend, I felt hollow inside, though I normally love buying gifts. In store after store, I found myself bleary-eyed and dazed, picking up objects—a bright scarf, chocolates, a shiny necklace—and then putting them down again. Is this good enough? I’d think. Is it worth the price? And, shamefully: How much have I spent on this person already? How much more do I have to give?

Weary of all this holiday-fueled anxiety, I thought then about giving more charity contributions as presents this year: maybe some gifts from (predictably enough) Oxfam America Unwrapped, but also contributions to anti-poverty groups here in Massachusetts, where a record number of families are homeless this winter. Doing so feels a little better than just going through the motions, pretending everything is the same as it’s always been.

When I walked back to the boy and his dad, the kid turned to stare at me, the lone pedestrian heading in his direction. I looked away, embarrassed, as I shoved a folded dollar bill into the empty coffee can in his father’s hand.

“Thanks,” said the father quietly. Unlike his son, he barely looked my way; he kept his eyes on the sunset overhead, blooming pink and orange and purple above the ragged city skyline.

My gift given, I turned away. Head down, I joined the stream of people flowing down the block toward Newbury Street, clutching bright shopping bags in their hands.