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Credit Juliette Borda

This is definitely going to sound insensitive, but I have been thinking that life would be easier if the homeless had ID stickers with their stories: “Off Meds”; “Opioids”; “No Health Insurance”; “College Kid Using Kittens to Hustle You.” Not easier for them. Easier for the casual do-gooder in a hurry.

I feel especially mistrustful of the kitten users. Once the kittens have gone through the cute stage, I suspect they’re going to be dumped. And even if not, those kittens have already suffered a roller coaster of elation and disappointment.

Woweee! I am so lucky, I am going to be adopted! Oh, no! She’s got a permanent marker and a piece of cardboard.

On the other hand, that young panhandler with the kitten may have been tossed out of her home because of familial intolerance, perhaps a discordant sexual identity, although in Greenwich Village it’s hard to think what that would be. She grabbed what she treasured most, her nose ring and her kitten, and after weeks of unsuccessful job hunting finds herself on the street. That kitten is all she has to love her. And considering the depth of cat love, that is not much.

You see how confusing it is. One wants to do something, but there are so many bereft people in the street it’s difficult to know who to help and what to do. This may be why, when I read about feminine hygiene gift bags, I liked the idea so much. Tampons, I learned, are a relatively expensive item, which are often in short supply at shelters. So you pack a large handbag with tampons, add baby-wipes, toothpaste, underwear, socks, tissues — anything that might help someone clean herself up and maintain a bit of dignity.

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I go on Amazon to stock up. In addition to the basics I find a few luxury items: chocolates, scented soap, cologne — a spray of something lovely might transport someone, I think, even if just for a few moments. As Amazon offers items in bulk I have enough for two bags. I find the bags at Goodwill. One is a soft gray quilted tote; one is a patterned French knockoff. I put $10 in each bag so the freshened-up lady can get a cup of coffee and a muffin. While I wait for the items to arrive, I case my Union Square neighborhood. I spot the perfect recipient, a woman sitting on the street on Park Avenue South at the corner of 17th Street. She is in her late 20s or early 30s, with a backpack and a cardboard sign.

“Better homeless than a victim of domestic abuse,” the sign reads.

As soon as my items arrive I rush back to 17th Street. The perfect recipient is gone; the person now sitting on the sidewalk with a sign is a young man. I move on through the neighborhood. This makes me realize a few things: There are far more homeless men than women in the street. When it is winter and someone is huddled under layers of protective covering, it is not easy to tell who is male and who is female. I see only one homeless person I am certain is a woman, who appears to be deranged. After an hour and a half, I have given away nothing.

“The problem is, I want to give the bag to someone who will use it,” I explain to my friend Herb over dinner. “I don’t want to give it to someone who is so far gone she’ll put the Tampax in her ear. I don’t want to get up the next morning and see the underwear scattered all over 14th Street.”

“It can’t work that way,” Herb says. “It’s a gift. You have to hand it to somebody and not look back.”

“That might be O.K. if I had dozens of bags,” I say. “But I just have two. I’m not being unrealistic here. I just want to give it to somebody who will take it into Starbucks and be able to clean up; then she’ll look better and feel better and get a minimum wage job and within a year she’ll be a vice president. Or maybe she’ll be one of those people who writes a play about being homeless a few years later.”

I widen my search to Grand Central. The few women I see seem to be in no shape to care for themselves. One is wearing a blue bunny costume and is seated next to a stack of garbage bags filled with clothing and magazines. Another, an older woman in layers of clothing, comes at me yelling. I back off, frightened and thinking she isn’t the sort of homeless person who I want to give my bag to anyway, and am ashamed of both feelings.

A friend I’ve told about the gift bags has told me that the women I’m searching for go to shelters in freezing weather, that the ones who remain in the street have serious mental problems like dementia and schizophrenia. I think she may be right. On my third day of fruitless searching, when I see a young woman sitting on the sidewalk with two cats on leashes, asking for money, I stop. She may be a hustler, but if sitting on the sidewalk in December is the best way she’s got to make a buck, it’s a pretty bleak hustle. And she’s age appropriate and I’m tired. I give her a bag, wish her luck and leave town for a few days, glad to be taking a break from the gift bag project.

I return just in time for a cold snap.

The morning temperature is 9 degrees, it’s unlikely anyone will be in the street, but I grab the gray quilted bag anyway and take the train to my Upper East Side appointment. There are no homeless people on the train or the street. Then, returning downtown, just past the gate of the 67th Street subway station, I spot someone. He or she is wearing a dark parka and a black face mask and holding a coffee cup with a few bills, and is asking for change. I think the voice is female but with the face covered I’m not sure. I walk up to the person, trying to figure out a polite way to ask. There’s nothing to do but blurt it out.

“Are you a lady?” I ask.

“Yes,” she says, “I’m homeless.”

I give her the soft gray shoulder bag.

“For me?” she says, stunned, but as far as I can tell from someone whose face is almost completely hidden, happy stunned.

“Yeah,” I say.

I put out my hand and we shake.

“Good luck,” I say.

Then I walk away. I’ll tell you the truth, it will be fine with me even if she doesn’t write a play.

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