31 DaysDay 28: THE CITY {the prompt follows at the end of this post}


My Kind of Town

When you’re homeless, you have a strangely unique opportunity to observe humanity from an obscure, well, actually, from an almost invisible perspective: people tend to look through you, past you, around you, even at you, but they don’t really see you. Oh, sorry, let me introduce myself. My name’s Clarence. The ascot? Oh, yes, there’s a story behind that and perhaps we’ll get to that. Anyway, like I said, being homeless lets me see people in ways that most people don’t, maybe because most people aren’t trying to see anyone but themselves. I don’t know. I try not to make too many judgements.

And the City? Well, I love this place. Always have. Boston is my kind of town. Isn’t that a line from a song? More songs about New York, I guess, and though I like New York, I love Boston. Beantown. A city built on freedom and guts. And where New York has a frenetic energy that almost overwhelms if you’re a visitor, Boston has a more arms-wide-open welcoming feel to it. The natives here tend to tunnel-vision their way from place to place, but they gracefully and deftly side-step the tourists who tend to travel in wide-eyed, open-mouthed groups, gaping at historic buildings and obvious tourist traps, following the Freedom Trail precisely and taking a moment to absorb the information on the historical marker before sprinting off for the next stop and the next placard.

Today is no different. The sun shines brightly overhead and off the glass of the upper stories of the Prudential and the John Hancock and glitters off the Charles River, casting pockets of shadows along the Freedom Trail and along Newbury Street. My favorite place on days like this is either in the Public Gardens beside the pond where the Swan Boats glide constantly around filled with gaggles of tourists and ducks quack hopefully for peanuts, bread and popcorn, or the courtyard in the Library.

The Library is an oasis in the middle of the foot traffic, the tourists, the noise of busyness of the City. It’s an oasis from the street and from the stares, the blank, unseeing stares that register homelessness as an issue or a concern but not a person. And, so, in the Library courtyard, someone like me can disappear in a different way. I’ve discovered that if you sit in exactly the right spot inside the courtyard, you can’t see the Prudential Tower or the John Hancock Building looming high. You can’t see the hotels or the brownstones. You can almost imagine that you are somewhere in the countryside, some romantic setting.

Few tourists or natives settle in here. Tourists have too much to see in a short period of time and the natives have to much to do before the sun sets. Me? I can amble a bit. I can bask in the quiet and the solitude of the courtyard with its bright colored flowers, its peaceful flowing fountain, it’s green grass. And here? Nobody looks through me, nobody bothers me with their awkward acknowledgments. Here, I am just me. Clarence. No longer homeless. No longer faceless. No longer a statistic. Clarence.


Unfortunately, the sun sets and the day winds down and the Library closes and the crowds thin and I am no longer Clarence. I am homeless once again, a man of the streets, a man of loneliness. A man of sorrow. Where the day’s energy and the Library courtyard provide hope, the night’s darkness and the lonely streets bring despair. That’s usually when my path seems to cross Laurel’s. She’s not an angel exactly, but the way our paths intersect is certainly almost otherworldly. Divine, really. She tends to emerge from the shadows of Newbury Street onto one of the many side streets. Or from Beacon Street near the Charles. There are so many, I marvel that she always chooses the one upon which I am meandering, making my way somewhere I haven’t yet determined yet.

Laurel is an artist and a native and a kind-hearted soul. She was one of the first people to see me in a long time. Mind you, I didn’t give her much choice during our first encounter, I pretty much accosted her, ranting and berating her because there was no one else to yell at and I’d been wanting to yell at someone, to be heard, for way too long. And so there she sat and there she continued to sit as I let loose every crumb of anger I’d been cleaving to. And when I finished? She stood up and said that she needed coffee and that needed coffee. And so, we set off in search of coffee.

Since then, she seems divinely appointed to find me where I am, even in a city this size. Even in the darkness and the shadows of the tallest buildings or the deserted alleys of the brownstones along Beacon Street. The moon hides and seeks behind clouds and behind buildings as I move through the night and the streets of Boston. Night brings a different energy to the City. The tourists are tucked away in their hotel rooms, venturing only as far as a popular landmark restaurant, like Cheers or Legal Seafood or Dick’s Last Resort or, if they’re camped down by the harbor, they flood the Salty Dog or The Purple Shamrock or the Black Rose. The natives, on the other hand, move deftly through the shadows to local pubs and eateries, with some who are hoping to impress dates or potential business partners, choosing to dine along Newbury Street.

Couples stroll along Boylston, Beacon, Commonwealth and Newbury; every night is date night in the City for the young and the trendy and the old and established. Street lights and headlights blend into a subtle daylight along the busier streets and the lights of the windows of the Prudential and John Hancock twinkle like stars above the crowds. They are the few stars the city enjoys with the wash of light drowning out the night sky. In the distance, along Commonwealth, the lights of Fenway glow like a beacon, a siren song for natives and tourists alike.

And then, there me and my crowd. Even more than the day, the night brings a cloak of invisibility that is thicker. While restaurants bulge to overflowing, the corners of the subway stations and tucked in doorways, my population fades away. Some will pass and offer leftovers, some will pass on the other side of the street. Most will pass without noticing. And as I wander over broken bricked back alleys and ponder where I am from where I’ve come, she crosses my path. My Laurel stands before me, two white styrofoam togo containers in hand, bathing her in what one could easily mistake as an angelic light. She doesn’t dine with me every night, but she almost always provides me dinner and usually meets me for coffee most mornings.

Perhaps Laurel is the reason I prefer Boston over New York.


{Just a reminder, we try to keep these writing exercises to 30 minutes maximum, but that’s not a hard and fast rule, especially with these exercises and this challenge. And I will say that in order to keep my writing within the 30 minute time, I create playlists on Spotify that allow me to put together songs that come close to 30 minutes. I also select music that fits with the story idea and help inspire the words I write. When the final note plays on the last song…I stop writing. Usually. But not lately.}

Writing Prompt: THE CITY – Write two short scenes in a cityscape you know well, one during broad daylight and the other late at night. Cities are vertical as well as horizontal spaces, so make sure you keep the reader aware of the full picture. One of the common traits of a city is unexpectedness – you run into people you don’t expect to run into; you often find great beauty cheek by jowl with awful ugliness, and poverty and wealth hand-in-hand – so play with this. Don’t be tempted by cliches: A city at night need not be dangerous or foreboding. {Exercise 112 from The 3 A.M. Epiphany: Uncommon Writing Exercises that Transform Your Fiction by Brian Kiteley. Note, this is an affiliate link}


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