Something was wrong with Mr. Fleeter. 

He was usually so approachable, happy to talk with anyone. Unlike other teachers who struggled to connect with students, he never seemed to need anyone’s approval, which made us want to talk with him more. You could just tell he had a real-life outside of school. For starters, he was young, especially for this faculty. He didn’t wear a tie. His collared shirt would come untucked during the day as he stretched to write on the top of the whiteboard, and he’d look more natural that way. He was a good teacher (ask anyone) so it was rare to get him off topic in class, but when he did shift over to stories about the Peace Corps or traveling solo in Colombia or enjoying his neighborhood in the Bronx, he reminded us of the outside world where we wished to live after graduation. In this distant but very real world, one discussed literature in Ukrainian coffee halls between lulls in techno music, one traveled via horseback in Chile when the local bus union inevitably went on strike, one spoke French and Russian, and Spanish because it was needed to survive, not because there was a vocab quiz the next day. 

He was like us in so many ways; or rather nothing like us now, but who we might become. He didn’t live in the suburbs. He didn’t grow up in a house decorated with life-size oil paintings of his grandparents. He didn’t even go to private school. But we could all see ourselves in his shoes—the freedom to make our own definitions of importance. 

Naturally, he was the first teacher we approached to sponsor Homelessness Day. 

Sitting at his desk in the modern language office, Mr. Fleeter breathed deeply, paused to choose his words, and said, “That’s a very bad idea.” 

It surprised us that he wasn’t inviting a conversation to help improve our concept. 

“Volunteerism,” we countered. “Empathy. Sacrifice. Risk-taking.”

All of his buzzwords.

“There’s no risk,” he said. “Pretending to be homeless for a night, sleeping outside on the field behind the gym, that’s not sacrifice.”

“The temperature will be low,” we promised. “We’ve researched authentic practices. We 

can get all the cardboard we need to sleep on from the dumpsters at ShopRite. We’ll understand what it’s like to experience homelessness and later in life be more receptive to the struggles of others.” 

“I’m not insulting you,” he said. “I’m just saying this won’t help you to understand.” 

A rumor began that day, but it wasn’t unkind gossip—if anything it heightened his aura. It became accepted school folklore that, at some point in his past, Mr. Fleeter had been homeless. 

He’s such a badass, we all thought. 

Mr. Fleeter never officially agreed to help us—it was more like someone (perhaps someone on the student council) went to Principal Allen and said we needed a teacher to chaperone an overnight trip, someone who had experience traveling with students, someone who was on the younger side with no childcare conflicts, someone in good enough health to endure a cold night— not so cold Principal Allen, no worries—someone who needed to fulfill his contractual obligation of three afterschool events each year. Is there someone like this, Principal Allen? Someone who could also speak Spanish with the custodial staff to make sure the correct doors remained unlocked if we needed to get inside for the bathrooms? You think Mr. Fleeter would be suitable? That’s a great idea, Principal Allen! Would you mind asking him to support our efforts? 

Unbeknownst to Mr. Fleeter, we also invited an expert on homelessness to speak. 

Principal Allen was always saying how it was important to connect with our school’s roots. Even though Newark Academy fled its original urban location during the race riots of 1968, settling in a quieter, greener, corner of New Jersey, it was still our history. The city center was only ten miles down South Orange Ave, and it turned out finding a homelessness expert was easier than we expected. As soon as we arrived at St. Ann’s soup kitchen and offered a hundred dollars (we should have started lower!), we had our choice of speakers willing to help educate our students. 

As Mr. Fleeter frequently said, there’s no substitute for real-world experience. 

Mr. Jerry (we never learned his last name) arrived on time in an Uber we arraigned from Union Station Newark. He observed our setup of students lying on cardboard, six feet apart, nodded his head, and said, “You all need a fire.” 

An image of a barrel fed with abandoned issues of the student newspaper filled out heads. We turned to Mr. Fleeter, who said: “No fires on school property.” 

“All good,” said Mr. Jerry as we formed a circle around him. “Okay, okay. You got questions.” 

We’d prepared sensitive questions. Depending on the mood of our speaker, his forthrightness, we’d then shift to improvised inquiry. 

“How did you become homeless?” 

In short, it happened quickly, and he didn’t even know he was homeless, homeless until he was on the street, sleeping under the overpass next to Union Station for three days. 

We nodded. We knew that bridge, we’d been there.

“Was it true that wool retained its insulating properties even when wet?” 

Mr. Jerry didn’t know. 

“What social services are available for those experiencing displacement?”
Mr. Jerry had no clue.
“How did you extract yourself from homelessness?”
A cousin with a couch to sleep on. Part-time and then full-time work at the airport. “That’s all the time we have for questions,” said Mr. Fleeter. 

Indeed, it was getting dark. The weather app on our phones reported 39 degrees. It wasn’t scheduled to get colder. If this was as cold as it got, we’d all be fine. 

“How can you tell someone’s really homeless?” one of us asked Mr. Jerry, as a final question before his departure. “How do you know they’re not just trying to get money from you on the street, taking advantage of you?” 

“Absolutely, yes,” said Mr. Jerry, bouncing his head in agreement, confirming the essential nature of this question. “There’s a look. I can just look at a guy right in the eyes and know, yeah, this isn’t his life, you know? When you’ve been there, you just know.” 

We looked at Mr. Fleeter for confirmation of our engagement. We were learning

When Mr. Jerry’s return Uber arrived, we all took off our gloves to shake his hand. After, we went over the ground rules: 

One layer of cardboard apiece, with nothing else to serve as buffer between the cold earth and the sleeping students. Coats, gloves, and hats were fine and encouraged, but we all had to remove our shoes and place them next to our heads as we slept. Those needing more clothing were welcomed to visit the school’s lost and found but had to return the layering items in the morning. The gym bathrooms were for emergencies of magnitude only; otherwise, the woods by the soccer field provided sufficient privacy. No one could go inside for warmth unless they demonstrated symptoms of hypothermia. 

And that was it. Survive the night and arrive to convocation on Monday morning to share our experiences with the full student body. 

No one made a big deal when Mr. Fleeter returned from his car with a tent and what looked like a portable heater—both items in direct violation of our established parameters. When he zipped himself into his tent (after getting it all set up with lightning speed), it was clear he wouldn’t be telling us stories to help pass the night. 

Some of us attempted to study for the upcoming SATs by flashlight, but that didn’t last long. We weren’t tired, but it seemed appropriate to take off our shoes and begin our night of homelessness. 

A loud bang focused all our attention on the school.
The door to the gym closing wasn’t a problem, not at first. No one looked panicked. If necessary, Mr. Fleeter would be able to call over a custodian and open it back up. We looked at his tent. The light was out. If there was an emergency, sure, we could wake him up. But no one wanted to do that. No one liked coming into work on a Saturday—let’s give him a break. We’d have to give him a special shout-out during convocation, make sure everybody clapped. 

The temperature never dropped below 39 degrees, though we constantly checked our phones for updates, poking at the screens through mittened hands. 

The locked gym door soon became a problem. 

We’d bonded with Mr. Jerry over hot chocolate, and now, several hours later, the bathroom situation was no longer in the background of our minds. 

Our feet, at first only somewhat chilled, were now tingling without proper circulation. No amount of lost-and-found fleece wrapped around our ankles could keep them warm. When we decided to put the shoes back on, as a group, we were discouraged to learn the boots barely helped. 

Once you were cold, you stayed cold.

“This could get dangerous,” someone said. “What if we can’t get inside?”

“Wake up Mr. Fleeter,” said someone.

“No,” someone else responded. “You do it.”

The Mr. Fleeter we knew wouldn’t leave us to freeze to death on the spit of manicured grass between the gymnasium and the soccer field. Some of us thought he was trying to teach us a lesson, not out of spite, but out of the same impulse that forced him to encourage us through difficult lessons without giving us the answers too quickly; his quizzes were impossible, but his tests were easy. 

After the first kids returned from the woods next to the soccer field, many were thinking that Mr. Fleeter really should have been more attentive to our needs. This wasn’t like him. We weren’t going to tell our parents or anything, no, but a shout-out at convocation was no longer a given. A working theory emerged: Mr. Fleeter had closed the door on purpose or had one of the janitors do it. 

Daylight. Reprieve. 

We’d barely slept. We hadn’t eaten. One of us, despite claims otherwise, had absolutely defecated in the woods. 

Mr. Fleeter was still cozy in his tent. 

When he finally emerged and walked over to the gym door, we watched. He grabbed the handle. We held our breath. He opened the door with no apparent resistance and went inside, presumably to use the facilities. 

No one looked at each other. 

We didn’t talk to Mr. Fleeter when he reappeared, giving him the cold shoulder as we folded our cardboard and placed it in the industrial recycle bin in the parking lot. Our parents came to pick us up, and we didn’t thank him. He hadn’t given us anything more than his time, and wasn’t that the baseline expectation when you worked with kids? 

Still, Mr. Fleeter, you had to admit, was great with parents.

“They did a good job,” he said. “They got done just what they intended to do.”

Our parents smiled and (once the car doors closed) called him a nice man, a good teacher, before pulling out of the parking lot and changing the subject.

Four of us remained, waiting to be picked up. We sat next to our rolled-up sleeping bags on the curb, our oversized backpacks filled with textbooks for the weekend’s homework holding us in place. 

“It shouldn’t be long,” we said. 

This was a lie. It would be very long until our rides arrived, and everyone including Mr. Fleeter knew this. We four had been here before, waiting, presumed abandoned, emergency contacts called, frantic parents rolling down the window to apologize when they finally arrived with a breathless explanation that we knew to be either embellishments or blatant lies. 

The only question, today, was who would be last?

Well, it was me.

Perhaps too embarrassed to arrive in person, my parents had sent an Uber that arrived simultaneously with a text message to show Mr. Fleeter.

“All good, Mr. Fleeter! The ride is on the way!”

We’d done this before, the uber pickup, after the field trip to Gettysburg returned and my parents were nowhere to be found after two hours.

Mr. Fleeter read the text and nodded. “Technically, I need to hear their voices, so I know you’re not being kidnapped. Or plotting your escape from the country without their knowledge.”

We both smiled. I liked that he thought I had the street smarts to plot my escape into the world. I thanked him for staying. It was his job, to stay, but it seemed right to thank him. It made me feel good as I got in the car and put on my headphones. My phone died instantly, the battery life murdered by the night’s cold. I kept my headphones in any way so the driver wouldn’t feel the need to talk to me. I’ve learned many adults are not great at talking to kids.