I (50M) have been walking through Riverside Park every morning for the last four years. Same bench, same coffee, same twenty minutes before I have to be a person again. I’m a senior partner at the same firm I’ve been at since I was thirty-two. I make more in a month than most people make in a year. I say that not to brag but because it matters to what I did next.
There’s a woman who sleeps on the east end of the park. I’d seen her maybe a dozen times over the past few months – matted hair, a sleeping bag that’s more gray than whatever color it used to be, a cart with two plastic bags hanging off the handle. I gave her a wide berth the way you do. I’m not proud of that either.
This morning I sat down with my coffee and she was on the next bench over. Closer than usual. And something made me actually look at her face.
I put my coffee down.
Her name is Donna Hartwell. Or it was. We worked together at Mercer & Finch for six years starting in 2004. She was a senior analyst. She was GOOD – the kind of person who made everyone else in the room feel like they were half-paying attention. She had a daughter, a condo in Midtown, a laugh you could hear from two floors up. I went to her birthday dinner in 2008. I remember the restaurant.
She was looking right at me.
I didn’t know what my face was doing but she saw something in it because she said, “I know.”
I said, “Donna?”
She said, “You don’t have to.”
I didn’t know what that meant. I still don’t, entirely. We sat there for a minute and I asked how she was doing, which was a stupid thing to ask, and she just kind of smiled and said she was okay, that it had been a long few years, that she didn’t need anything.
I told her I had cash. She said she was fine.
I asked if there was someone I could call for her. She looked at me for a long time and said, “You haven’t changed at all, Dennis.”
I don’t know why that hit me the way it did.
I sat there for another few minutes. Then I got up. I said it was good to see her. She nodded. I walked to my car and I sat in the parking lot for twenty minutes and I thought about every single thing I have and every single thing I just did, which was nothing.
My friends say I can’t force someone to accept help. My wife says I did what I could. But here’s what I keep coming back to – I have her first name, her last name, her work history, and probably enough connections to find out what happened and who she still has in her life.
And I haven’t done a single thing with that.
But this morning, when I got to work and opened my computer, there was an email in my inbox from an address I didn’t recognize.
The Address
The subject line was blank.
I almost deleted it. I delete a lot of things with blank subject lines. But I’d been distracted since the parking lot, and I was clicking through my inbox on autopilot, and something made me open it instead of sending it to trash.
The sender was a Gmail address. A string of numbers after a first name. The first name was Caitlin.
The email was four sentences long.
Hi Dennis. You don’t know me but I think you spoke to my mother this morning in Riverside Park. Her name is Donna. I saw you from the path and I recognized you from an old photo she kept. I’d like to talk if you’re open to it.
I read it three times.
Then I sat back in my chair and looked at my office ceiling, which is twelve feet high and which I have stared at during maybe two hundred bad phone calls over the years, and I thought about Donna’s daughter. In 2008 she would have been, what. Eight? Nine? I remembered Donna showing me a school photo once, the kid with two missing front teeth and a purple sweater, sitting on one of those fake cloud backgrounds they use. I couldn’t remember the daughter’s name. I’d forgotten it completely.
Caitlin.
She was watching from the path. She saw me sit down, saw me talk to her mother, saw me get up and leave.
I don’t know what her face looked like when she watched that happen.
What I Know About 2010
I left Mercer & Finch in 2009. Not dramatically, just the way people leave firms – a better offer, a handshake, a going-away cake in the conference room. I didn’t stay close with many people from that chapter. You tell yourself you will. You don’t.
What I knew about Donna after I left was almost nothing. I heard through someone, maybe 2011 or 2012, that she’d had a rough stretch. I didn’t ask what kind of rough. I was busy. I had my own rough stretches by then, though nothing that ever put me anywhere near a park bench.
What I’ve been doing since I got her daughter’s email is filling in the blanks the way you do when you have access to the internet and a name and a need to feel like you’re doing something without actually doing anything yet.
Donna Hartwell. Senior analyst, Mercer & Finch, 2004 to 2010. There’s an old LinkedIn profile, not updated since 2011, photo that’s clearly her but fifteen years younger. A mention in a 2007 financial trade publication, one of those “thirty professionals to watch” roundups. She’s third on the list. The blurb calls her “a sharp and unconventional thinker with a particular gift for distressed asset analysis.”
Distressed asset analysis.
I keep coming back to that phrase and I know it’s too neat and I’m not going to make it into anything. But I keep coming back to it.
After 2011, nothing. No LinkedIn activity. No professional footprint at all. One property record from 2012, a Queens address, a lease dispute in the public filings. Then nothing.
Sixteen years of nothing, and then a sleeping bag in Riverside Park.
The Daughter
I wrote back to Caitlin at 11:14 in the morning. I said yes, I’d like to talk, and I gave her my direct number at the office.
She called at 11:52.
She’s twenty-six. She sounds nothing like her mother, voice-wise, but she has the same thing Donna had where she gets to the point without making you feel rushed. She said she’d been trying to help her mother for three years. She said her mother was not, technically, without options. There is a sister in New Jersey. There is a caseworker she sees irregularly. There is a storage unit in the Bronx where most of Donna’s things have been sitting since 2019.
“She’s not lost,” Caitlin said. “She knows exactly where she is. That’s kind of the problem.”
I asked what she meant.
She was quiet for a second. “She made choices. A lot of them were bad. Some of them weren’t her fault. She’d be the first to tell you the ratio.” A pause. “She doesn’t want to be rescued. She’s told me that pretty directly.”
I said I understood.
“Do you?” She wasn’t being mean about it. Genuine question.
I said probably not entirely.
“She saw you coming from pretty far away this morning,” Caitlin said. “She moved to that bench on purpose.”
I hadn’t considered that. I sat with it.
“She wanted to see what you’d do,” Caitlin said. “She does that sometimes with people she used to know. She calls it a field test.” Another pause, shorter. “You’re not the first person she’s run into.”
What Donna Wanted
I asked Caitlin what she wanted from me. Not harshly. But I needed to know what the call was for.
She said her mother hadn’t asked her to reach out. She’d done it on her own. She’d recognized me, looked me up, found the firm. She wanted to know what I was going to do.
“She’s not going to ask you for anything,” Caitlin said. “She’s not going to let you write a check and feel better. I’ve watched people try that.”
I asked what had happened with those people.
“They felt better,” she said. “She didn’t.”
I asked what would actually help.
Long pause. Longer than the others.
“She had a case manager she liked, a woman named Phyllis, through a nonprofit that lost its city funding in 2022. The program shut down. Phyllis still works in that space somewhere but I don’t know where.” She stopped. “You have connections I don’t have. I’m a twenty-six-year-old who works in a dental office in Astoria. I can’t make calls that go anywhere.”
There it was.
Not a check. Not charity. Not me sitting across from Donna in some office while she nods politely at my guilt. A specific name. A specific problem. A thing that might actually be findable.
Phyllis.
What I Did After I Hung Up
I have a friend, Gary, who sits on the board of three nonprofits and who has been on me for years to do more with my money than write anonymous checks to organizations I’ve never visited. I’ve always said I would. I haven’t.
I called Gary at 12:30.
I told him the situation, most of it. He didn’t editorialize. Gary is good that way. He made two calls while I held, put me on hold for about four minutes, came back and said he had a name.
The woman Caitlin called Phyllis is Phyllis Garber. She’s a case manager at a transitional support organization in Washington Heights. She’s been there since 2023.
Gary had her direct line.
I wrote it down on a Post-it note and stuck it to my monitor and I stared at it for a while. I thought about Donna moving to the closer bench on purpose this morning. I thought about what Caitlin said – she wanted to see what you’d do.
I thought about the field test.
I called Phyllis Garber at 1:15. I got her voicemail. I left a message that was probably too long, said I was a former colleague of a woman she may have worked with, that I had some information I thought might be useful, that I wasn’t looking to disrupt anything, that I just wanted to make sure there was a thread connecting the right people.
She called back at 3:40.
She remembered Donna immediately. No pause, no searching. Just “Yes, I know Donna.”
I told her where Donna was sleeping. The east end of Riverside Park, the bench near the Seventy-ninth Street entrance. She said she’d been looking for her since last fall. She said Donna had stopped showing up to their weekly check-ins and hadn’t responded to outreach. She said she was glad to know she was okay.
“Okay is relative,” I said.
“Yeah,” she said. “It always is.”
We talked for another ten minutes. I didn’t offer money. I didn’t try to take over. I just gave her what I had: the location, the timing, the fact that Donna’s daughter was reachable and wanted to be in the loop.
Before she hung up, Phyllis said, “How do you know her?”
I said we used to work together.
“Were you close?”
I thought about the birthday dinner. The restaurant on Fifty-second Street. Donna ordering the branzino and arguing with someone from compliance about municipal bond ratings and laughing so loud the table next to us looked over. I’d thought it was funny at the time. I’d thought she was a little much.
“Not as close as I should have been,” I said.
Phyllis didn’t say anything to that. Just thanked me and got off the phone.
Tomorrow Morning
I’ll go back to the park. Same bench, same coffee. I don’t know if Donna will be there. I don’t know if Phyllis has already been out to find her, or if Caitlin has called her mother, or if any of this has changed anything at all.
I’m not going to walk up to her with news of what I’ve done. I’m not owed a reaction. That’s not what this is.
But I’ll go back.
I’ve been thinking about what she said this morning. You haven’t changed at all, Dennis. I spent most of the day deciding she meant it as an accusation. By 4pm I wasn’t sure. By the time I got home and my wife asked how my day was and I said fine, I’d decided I didn’t know what Donna meant and I probably never would and that was going to have to be okay.
What I know is this: I sat in that parking lot for twenty minutes this morning doing nothing except feeling bad. And feeling bad is the most useless thing a person with resources and connections can do.
I’m not the asshole for walking away this morning. I don’t think that’s the right question.
The right question is what I do with tomorrow morning.
—
If this one stayed with you, send it to someone who needed to read it today.
For more stories of unexpected encounters and complicated ethical questions, check out “I Came Into My Shop at 5 AM and Found Cots, Strangers, and Dale With His Hands Up” or even “My Brother Vanished the Night After Our Mom’s Funeral. He Showed Up on My Porch Nine Years Later With a Letter She Made Him Hide From Me.” And for a different kind of moral dilemma, read “My Seven-Year-Old Saw What I Spent Forty Minutes Pretending I Didn’t”.
