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A Heartbreak in Fragments

Recovering from a bad breakup in a new city.

By Featured, Literature

Illustration by Allen Ye.


Three months before my boyfriend broke up with me, we held each other tightly in my bed crying. It was the eve of our last Valentine’s Day together, and we knew the relationship had an expiration date. 

The end of college was less than a hundred days away, and to keep my student visa, I would be moving to Chicago in the Fall to start a master’s program. He would be staying in Boston. 

My lover turned his face away from me. He was tall, strong, and blue-eyed. His deep voice cracked between sobs. 

“You have to go become a great writer,” he said, resigned to letting me go. A month ago, I moved to Chicago to become that great writer. These words echoed in my mind. 


The most common advice for a breakup is: 

1) Spend time with friends and family. 

2) Go to your favorite places and do things that you love. 

Starting fresh in a new city, you have neither.


I’ve been told that his letting go is a sign of his true love for me: a selfless willingness to let me walk unburdened into this life of writing that has always called for me.

But why was he an impediment to my journey? Why was he unable to walk with me? 


I was bedridden for three weeks after we broke up. 


My doctor said a few years ago that I had to go on hour-long walks every day. This was easy with my lover in Boston. We used to walk alongside the Charles River Esplanade, all the way to the Smoot Bridge, and then loop back onto cobblestoned Commonwealth Avenue, through the Boston Common, to the urban campus of Emerson College in the Downtown Theater District. 

Every season brought new colors to our walk: reds and oranges in the Fall, green and blues in the Summer, pearly white snow in the Winter, and pink cherry blossoms in the Spring. He was good at walking long distances — he was a runner. It was always me with my bad knee and my bad hip that had to often stop and rest on a park bench at the edge of the Esplanade. 


I’m looking for someone in Chicago to go on long walks with. 

If I could, I would stick a brightly colored ad onto every street lamp in the city: “Help Wanted: Friend or Lover Who Likes to Walk.” 


I’ve begun to go on dating apps. This was a suggestion from another ex of mine — an ex who I am now best friends with.

It took us a year of not talking to process our breakup. 

I wonder how long it’ll take my lover and me to mend the tears in our hearts. I haven’t heard from him in weeks. 


I don’t know where my new friend and I would walk around Chicago. I don’t know the city well enough to map out my ideal walk. I’ve taken strolls by the lake’s trails and by the Riverwalk, but I quickly become upset. Both feel like a personal “Fake Esplanade.” The city of Chicago feels like “Fake Boston.” 


I record these moments of “Fake Boston” on my social media with the sole intention that my lover will see them. I photograph Chicago extensively so that it seems like I am already in love with the city. It is all a lie. I am alienated from my environment despite its objective beauty. 


Everyone I have met so far in Chicago loves Chicago. They go out of their way to tell me it is a fantastic city to live in — to create art in — but I have not yet found this love within myself. Part of me thinks if I was not abandoned, I would be excited to explore this city too.


It’s been four months since our breakup and I still cry every night. 

When you’re bitter and bruised, even the smallest of triggers make you blue. 


I am in a poisonous era of my life. 

I meet strangers on the internet and take them to my apartment to fill up that empty space. It’s risky behavior, but my heart races at the rewarding prospect of not being alone. 


I envy everyone I know in a long-term relationship — especially when they post about it on the internet. Moments like those make me wonder if things would be different if I had asked once, “Would you come to Chicago with me? Could we try to make it work?” 


Everything is a trigger. 

Kraft Mac and Cheese. The Parquet Courts. Las Vegas. 


A common sign of a manic episode is risky sexual behavior. 

I don’t sleep with these men. I just like the idea of their company. 

I am not manic — I have been manic before and can recognize the feeling — I am energetic in my depression. 


I have the belief that everything I am looking for is also looking for me. This comfort, this companionship, this happiness. It is all searching for me too. I go out to parties on most nights so that love can find me. 


Chicago’s “L” Blue Line looks similar to Boston’s “T” Blue Line. 

I take this train every Thursday on my way back from pole dance class and I pretend I am home. 


I become physically ill, grappled by sadness, every time I think about my old life.


I can’t look at the men I match with when we meet at museums. I am repulsed by their physical qualities. It’s not that they’re ugly. They’re just not him. 


I only started going to pole dance classes because my lover enjoyed doing inverse spins on his friend’s pole at parties. 

I thought about quitting classes after the breakup, but I kept having these vivid dreams about twirling on the pole. 


I dream about him every night. 

It’s hard waking up alone when I get to touch him in dreams.


It’s harder falling asleep in an empty bed. 


I haven’t gotten a dating app match in two weeks. 

“You’re gorgeous,” a friend says when I mention this. “Is it you who’s picky?” I nod. They’re just not him


I make a friend at pole dance class. We walk to the Blue Line together. 

“I didn’t know the Blue Line ran through this neighborhood,” she says. 

It doesn’t. 

The Blue Line I so love is actually the Green Line. It’s just that the station’s floor is painted blue. 


I search online for “the Esplanade” to catch a glimpse of my old Boston sights — even if just in pictures. 

Results for Chicago’s “River Esplanade Park” pop up instead. 


I never thought I’d miss Boston this much when I first moved there. Now I wonder, will I miss Chicago this much when I leave? 

I fear either response. 

If I do, I’ll be plagued by sadness all over again. 

If I don’t, it means I never fell in love with this city and its people — that my years here were a waste of time.

I’m afraid of feeling this sad for two years. 


I have to remind myself that it took me two years to fall in love with the friends I had senior year in college. 

It takes time to fall in love with someone and somewhere, but I do not have time. I have two years until my master’s is over and I have to move on again. 


I send my lover’s mother a postcard every month. We are still close despite the breakup. I can never remember her zip code in New England, so I search online for her street — hoping her full address will auto-populate on my screen like it always does. For the first time ever, the search engine takes me to an address in Illinois. 


During my last semester at Emerson College, I published an article titled Sunset Moments. In it, I argue that a sunset forces you to stop, stare, and reflect as the day comes to a close — just as life’s transitional moments force you to do so too. 

Now I wonder if the inverse is also true: Sunrise Moments. Periods in your life where you’re forced to stop and stare at the start of something new while still caught in the sleepy, immovable limbo of it all. 


Charles Dickens wrote, “One always begins to forgive a place as soon as it’s left behind.” This applies both to Boston and my lover. 


I used to cry on the phone every night to his friends — our friends. Where I was once met with empathy, I am now met with “you need to learn to move on.” 


I also wrote about this breakup in Sunset Moments. To those concerned, I’m almost ready to stop writing about the topic.

Katie MacLauchlan (MFAW 2025) has read a lot of books. She is the literature editor at F Newsmagazine.
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