I Was Homeless For A Night: The Bitter Reality of Boston’s Homeless Population

By: Isaiah Owens

With $8 in my pocket, I was instructed to buy dinner for myself, three high school students, and a homeless person. This was the most memorable moment from my mission’s trip in Boston, Massachusetts last week.


I am one of the leaders of my church’s youth group, and I was excited to embark on this journey throughout the city. After ten hours in a car, holding one of our student’s hair as she threw up, and fighting a splitting headache, we finally arrived at our destination, a welcoming looking church in Boston. The sleeping arrangements were decent, and we shared a space with two other church groups. The men’s bathroom had one shower, two toilets, and a sink, and as a two-shower-a-day type person this was trying, but I survived. Regardless of the living arrangements, the main reason for our stay was to help those within the city that needed it most. Throughout the week we helped teach children at a summer camp, prayed and talked with homeless people, and even made food for the terminally ill, but nothing impacted me more than the night I was forced to go homeless.


It was a cool Tuesday evening in Boston as our group guide for the week, named Angel, described to us the nature of our challenge. Angel said that every night tons of people would sleep in and around the Boston Common Park, and that tonight we were going to join them. I could see the look of surprise on our students faces as they heard those words. Even worse, Angel followed up by saying we would have only $2 each for dinner, and that we MUST eat with a homeless person as well. See, as a leader I was aware that we were going to be simulating homelessness that night, but not to the degree she proposed. What made things worse is that we had no cellphones, no wallet, not even a book! All we had were the clothes on our backs and the shoes on our feet, which unfortunately was more than some of the people that we encountered had that night.


The rules were simple, the time was 4 pm when we started, and all we had to do to complete the mission was make it until 8 pm. Not bad, right? Wrong. We broke off into groups and were sent free to go wherever we wanted in Boston. As the leader of three high school students in my group, two boys and one girl, I was instructed to let them run the show. Wherever they wanted to go and whatever they wanted to do I had to oblige to. All I could do was to be a voice of reason and encouragement when needed. After we were situated, we were thrust out into the urban jungle, without any idea of what to do next.


It was only the second day of our mission’s trip, and the three students weren’t quite sure what to do. Not entirely sure what to do myself, I advised them to start walking, because an opportunity was bound to come up as long as we kept moving forward. Ten minutes into our journey, that opportunity present itself through a man named Barry. We encountered Barry as we were walking through the Boston Commons, and we weren’t entirely sure whether he was homeless or not. After some hesitation, we greeted this strange man and began our conversation. To our surprise, Barry was both employed and homeless. Yes, he had a job, but with city rent for a one-bedroom apartment in Boston starting at around $2,500 a month, it was easy to understand why he was on the streets. Even more surprisingly, Barry had traveled the country before deciding to settle in Boston. He had been to San Francisco, Dallas, Philadelphia, Orlando and a variety of other cities. Figuring he would be hungry from his travels, we offered to buy him food with our $8 of combined living expenses for the night, which he declined, claiming he had already ate. Instead, he offered us a bundle of brochures highlighting everything someone could possibly do in Boston, which we took with gratitude, not because we needed them, but because it made him feel important.


Barry was a lucky find, because for about an hour after that we struggled to find anyone to have a meaningful conversation with. Almost at the point of giving up, my students and I stopped at a Starbucks to collect our thoughts. Beginning to get frustrated, the only girl in my group, Maddie, expressed how incredibly boring the entire experience was. Then it hit me. Maybe this experience wasn’t solely about helping the homeless, but rather being able to build empathy for them. In my moment of clarity, I explained to my three students that this was likely how homeless people felt every day. They have nowhere to go, nothing to do, and nobody to see in particular. All they have at their disposal is to go to sleep, lay there amongst the crowd, or to beg, none of which is extremely exciting. And minus the begging part, we were pretty much living the life of homeless young adults.


As we discussed, it was hard not to notice the various people bustling past our Starbucks window seats. The most noticeable of all was a despondent looking young man sitting across the narrow street from where we sat. Figuring that we didn’t have much luck besides Barry, we figured we would try talking to this young man. We quickly arose and walked out the door, leaving the sweet aroma of Starbucks behind, only to be greeted by the musty smell of the city. We pushed through the crowd until we reached the young man, and we greeted him with warm smiles. Up close, he looked even more depressed than he had from afar. When we asked him his name, he replied, “My name is Gage,” without even looking up from the ground, the same posture he had as we observed him from the window. We talked with him for some time, trying to understand what it was like to be homeless in Boston. He was reluctant to tell much, but I could discern enough to tell he was not much older than myself (I am 21) and he seemed to have given up on life. We offered to pray with him, but he refused, and all we could do was pick up and carry on.


Our luck finally changed as we wandered the city and stumbled upon a homeless veteran. I was heartbroken to see someone who gave so much for our country end up homeless. Without even consulting the group, I abruptly stopped and asked to pray for this man, named Rob, and he was happy to have someone pray for him. In fact, the stop was so abrupt that only one of my students, Ryan, even noticed enough to stop with me. The other two continued walking on, but being that I was in the moment I knew two things. One, I could still see them over my shoulder, and two, they couldn’t go too far before they realized we weren’t behind them. As I began to pray for Rob, I felt a flood of emotion sweep over me. I prayed for his safety, I prayed he would have the strength to keep fighting, I prayed that God would give him wisdom, I prayed that others would be as thankful as I was for this man’s sacrifice, and most importantly, I prayed that the overwhelming problem this nation has of failing to provide for our veterans would be remediated. The words seemed to pour out so poetically, I even surprised myself. As me and Ryan closed in prayer and looked up, a random woman was there who had heard our prayers and stopped to pray with us. I don’t know her name, but I remember her saying that she had heard our prayers and felt compelled to stop and join in. Rob was thankful, I could see the gratitude in his eyes. Sure, I didn’t talk to droves of people in such a heartfelt way as I did Rob, but that prayer was the most powerful moment in my four hours of being homeless, because it was so evident the difference it made.


At this point, the four of us were hungry. Enrique, my third and final student, believed that the 7-Eleven we saw earlier would be our best food option on an $8 budget. Not having any other ideas, we headed back towards the 7-Eleven that faced the Boston Commons where we began our journey. For some reason I can’t explain, our eyes became transfixed on this homeless couple sitting by the T, Boston’s subway system, moments before we entered 7-Eleven. In that moment, the four of us knew that these two people would be the ones we would eat with, but with only $8 that was easier said than done. Everything in the 7-Eleven was either too expensive, or not enough to feed six people. In my mind, I thought how inconvenient this was and resented the fact I didn’t have my wallet. But in my heart, I couldn’t shake the feeling that this was likely someone’s reality every single day. No fancy debit or credit cards, no bank accounts, no checking on the performance of stock portfolios, just a few crumpled up dollar bills to our names. We decided on buying a pizza that cost us about $6, and with about $2 left to our names, we walked over to have dinner with the homeless couple we had scouted out before-hand. With not much time left in our homeless experience, Ryan decided we should just give them the pizza and then meet up with our group, which is exactly what we did. The homeless couple was thankful for their dinner, and we briefly chatted with them before we knew it was time to go.


We took the subway back to the church, and I was starving after having not eaten anything in over nine hours. That night I cheated and went out to a local dive and bought pizza, and it made me feel sick to my stomach. It was as if God was punishing me for revolting against the whole, “don’t eat anything else tonight” experience. As I lay in bed with an upset stomach at the end of the night amongst obnoxious teenage boys from another church laughing about Lord knows what, I can say one thing for sure. As I mentioned earlier, the experience was just as much about empathy than it was actually being homeless, and I definitely felt empathetic. As I lay there, I couldn’t stop thinking about what had happened. What if I really did have to sleep outside tonight? What if I only had $2 left for my next meal? What would I do all day to keep myself occupied as people walked by me in blissful ignorance all day long? I would love to say I answered my questions, but I didn’t, and I pray to God I never will have to.



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