Tracey Folly
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I Dated a Homeless Man

I Dated a Homeless Man

Feb 16, 2024

As spring was heating into summer during my senior year of high school, I spotted a young man with fiery red hair while I was waiting for the city bus with my friend. I first saw him at the place where all the city buses converged downtown.

We were waiting for the same bus.

He was carrying a large olive green duffle bag. His long crimson hair caught my eye. It gleamed in the sunlight. I couldn’t stop looking in his direction. Waiting for the bus no longer seemed important.

My friend and I maneuvered our positions so we could be closer to him. I don’t remember how we struck up a conversation, but he asked me for money. Whenever I took public transportation to the city, I filled my pockets with change for bus fare. My pockets were heavy with quarters, dimes, and nickels.

I counted out enough change to get me back to my neighborhood bus stop. Then I passed handfuls of change into his cupped palms.

He thanked me and excused himself to go to the liquor store across the street. When he returned, he had exchanged my quarters, dimes, and nickels for several nips, those little bottles of alcohol you see in hotel honor bars.

I didn’t say anything about it; I’d given him the money willingly. Besides, I was already smitten.

When I was a high-school senior, he was already a convicted felon.

He told me that he’d served time in prison for counterfeiting. His arms were marked with ugly prison tattoos that looked like they’d been drawn by a child with a Sharpie.

Although we chatted a bit longer and exchanged names, we made no plans to see each other again.

I had other ideas.

The following day, my friend and I once again ventured to the city. I remembered to bring extra change. We virtually stalked him. He was easy to spot from a distance thanks to his hair.

We found him and brought him to Burger King for a meal. I gave him the extra change from my pockets.

We saw each other regularly after that day.

He and I wandered around the city. Sometimes my friend joined us; usually, she didn't. He always carried his enormous duffle bag over his shoulder. I learned that he was homeless. He said he’d served in the military. That’s where he’d gotten the bag.

His hair was long, flowing in waves past his shoulders, and it was the same vibrant shade of orange-red as a sunset over the ocean. He always wore a puka shell necklace and carried that bag; it contained all his worldly possessions.

One time, when he asked me if I had any spare change, I emptied my pockets into his cupped hands. It was enough money for him to buy several 50 ml nips at a nearby liquor store before the bus was due to arrive. He drank them at the bus stop and then wandered away, leaving me to wait for the bus alone.

I didn’t have enough money left to take the bus because I’d given him all my change. So I walked home. It was a long walk.

I always wondered whether I would ever see him again.

Armed with a pocketful of coins, I took public transportation back to the city several days later. I wandered around the plaza and hoped that lightning would strike the same place twice. It did. Eventually, I saw the unmistakable color of his hair shining in the sun. It looked like fire.

I followed him. Some would call it stalking.

When he noticed me, I offered him the coins from my pocket — minus enough for bus fare home.

He bought more alcohol, which he drank while we sat on a park bench and talked. That’s when I learned that he had recently gotten out of prison where he’d done time for allegedly passing counterfeit money. He showed me the tattoos he got in prison; he showed me his scars.

I admired his necklace. So he took it off and put it around my neck. In exchange, I gave him the delicate silver chain I wore. There was a sterling charm in the shape of an electric guitar hanging from it.

He promised to meet me in the park the following afternoon, following my day at school. He kept his promise and was waiting for me when I got off the bus. This time, he was already drunk.

He asked me to buy him a pack of cigarettes and complained fiercely when I declined.

I had a boyfriend when we met, but I didn’t care. It was love at first sight.

I broke up with my childhood sweetheart to spend the summer following my new love interest down dark alleys and into abandoned buildings.

His bed was a park bench in the plaza where he slept warily at night, always on alert and protecting his duffle bag. It contained everything he owned in the entire world. He ate from trash barrels outside Burger King and bathed in the basement bathroom of the local arcade.

One day, he said he was staying with friends just outside the city. We walked for miles and arrived at an old Victorian house with boarded-up windows. The apartment was empty except for an unplugged refrigerator in the living room and a couple lying on the floor beneath piles of dirty blankets in the kitchen. He acted like they weren’t there.

We never went back to the apartment, but he stopped carrying the duffle bag. Every time we met, I gave him change. He bought booze. I paid for dinner at a fast-food restaurant.

He wrote me poems that didn’t rhyme in a drunken scrawl on dirty napkins and called me from payphones to tell me he loved me.

Overall, dating a homeless man wasn’t that different from dating the other men I’ve known. The biggest difference was the massive duffle bag he carried and the fact that he bathed in the women’s basement bathroom of the local arcade.

By the end of the summer, it was over. Like getting together in the first place, breaking up was my idea. I returned his puka shell necklace, but he kept my silver chain.

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