The Upper East Side Awaits
Chapter One
Loving him means destroying our family's reputation, yet I have dreamed of being his ever since I laid eyes on him.
I was nine years old when my mother married Mr Ashford, one of the richest men in the Upper East Side of New York. My mother, my brother Daniel, and I relocated from Jersey to New York.
That was the first time I laid my eyes on Adam, my stepbrother.
We were still young at the time, but even then, I fell in love with him. It must have been the way he spoke, smiled, and how he carried himself. Some may even call it love at first sight.
Adam, Daniel, and I eventually became something in between. Not strangers. Not blood-related by family. Like a bond picked on purpose, then deepened without trying.
We became three little musketeers running through summer evenings, leaving smudgy footprints on the streets with laughter. We built entire galaxies using nothing but sidewalk cracks and breathless ideas. Adam showed up without needing an invitation- birthday parties, graduation ceremonies, and all the rooftop conversations.
Disguised underneath all that playful nature was a girl who yearned for time alone with him. We would look at each other long enough to feel something, but maybe it was all just my imagination, and hope that maybe he felt the same way about me, too.
We had quiet seconds that somehow seemed to last forever.
Until they didn’t.
A year was a long time to disappear.
Adam had left a year ago for Yale, chasing something bigger than obligation. He loved being on the field, chasing the ball. Game day noise filled his ears like music only he could hear. His passion for American football is what drives him.
We barely hung out once he joined the football team, and his passion for football grew every day. We would live in the same house, but only hold a conversation during family dinner dates. He barely noticed me, almost as if I didn’t exist anymore. We shared a simple brother-sister relationship, which hurt me, but I kept my feelings hidden inside every day.
It became easier once he left for Yale. At least now, I don’t get to see him every day and not be able to have him all to myself.
On the other hand, my brother Daniel headed off to Columbia, finding his rhythm in Manhattan's rush, building connections among the elite circles of the Upper East Side, and doing well in class.
Daniel would visit home every two months as a routine check, but for some reason, Adam stayed away and kept in touch through text messages, and replied days later.
Back home, I remained for my senior year.
I had felt the absence of Adam and Daniel as months went on without them. I knew I had to move on with my life without them.
Moving on meant stepping away from how things used to be with my brothers.
As months went by, I grew closer to Harper and Vivienne. The kind of people you lean on when everything else shifts. We were all in our senior year, so it was easier to be friends with them.
That April, talk never seemed to stop about which Ivy League school we would enroll in. Three friends caught up in the should I, and should I not? In Harper’s living room, as the sun went down.
“I’m seriously considering Princeton,” Harper said, going through her wardrobe searching for the dress she prepared for the Gala tonight. “I mean, the social scene alone is worth it, and I will be so much closer to my boyfriend at Yale.”
Vivienne replied, “Who is this new boyfriend of yours that you are constantly talking about?”
Harper smirked and said, “You will find out about him soon enough. For now, I am keeping him a secret.”
I replied, “Since when do you keep secrets from us?”
“Since I met him and fell in love with him,” Harper replied with a strong tone.
Looking into the mirror as I fixed my makeup, I said, “Anyway, I’m more worried about actually getting in than boys.”
Harper leaned closer, lowering her voice conspiratorially. “But you know… I think Leo has a crush on you.”
A small cough came out of my mouth, and I said, “The one from Harvard who plays football? That Leo?”
“Yes,” Harper said, grinning. “He’s obviously into you. Always showing up at games, always texting, always joking around just to make you laugh. Honestly, it’s kind of adorable.”
Vivienne giggled. “Well, maybe you should give him a chance. Harvard football isn’t Yale football, but he’s charming enough.”
I rolled my eyes and said, “I don’t even know if I am ready for that kind of attention, and yet alone, a boyfriend.”
Vivienne replied, “But would you be ready for your stepbrother, Adam?”
My expression changed as I said, “No, I would not. Besides, it's been a year since I saw him, and to him, I am just like his little sister.
I pretended not to care.
“I have seen you grow this year, and with that dress on, trust me, you wouldn’t be so little anymore,” Vivienne said.
Harper replied, “You know I have never been in support of this crush you have on your own brother, and no reasonable person would be. If there is a universe where you two actually end up together, it would humiliate your family, and you know that, so do yourself a favor and forget about him.”
I replied, “Firstly, if that universe existed, we would figure it out, and if it didn’t, we would create our own universe, and secondly, I always get what I want. It's just a matter of time and charm.
Vivienne replied, “Oh, so you finally have a plan for when he returns home this winter?”
I smirked and replied, “I don't need a plan.”
Harper replied, “Well, someone seems confident.”
Let's make a promise to each other that no matter what, we will always be friends, no Ivy League school or boy will separate us,” Vivienne said.
We put our hands together and promised.
“Are we actually ready for tonight?” Vivienne asked, eyeing herself critically in the mirror. “I mean, the gala — it’s the biggest social event of this season.”
Harper tilted her head, fingers tugging at the edge of her mask. Her dress would catch eyes, no question about it. The way the fabric dipped off one shoulder. People would stare. She knew that already.
My dress was smooth, black with a slit at the top of my thigh, hugging every shape exactly how I wanted — classy yet bold. My fingers pulled at the edge of the mask, making sure it stayed put. Maybe this is overdone, I thought to myself, maybe it was too striking.
A grin spread across Vivienne’s face as she looked my way, dressed in green so rich it seemed to glow beneath the hanging lights.
She called out, her voice warm but firm: “Elena, don’t hold back. Your moment isn’t coming — it’s already here. Ours begins when the clock strikes dark.”
Harper leaned in, whispering, “And remember — the right mask can make or break the whole look.”
I pulled air into my lungs, that old rush of thrill spreading through me. We went outside, heading toward the car parked up ahead.
The city glowed, reflecting light on our dresses.
“Imagine the people we will meet,” Vivienne said, leaning back, fixing her hair. “No holding back tonight. We are about to have the time of our lives, I can feel it.”
Harper nudged me, her grin mischievous. “And don’t forget Leo. If he’s coming tonight, you’re already on his radar. So don’t play dumb tonight.”
My eyes moved upward as I smiled.
Tonight, the city looked beautiful, shiny, and unpredictable.
When we arrived at the event, my pulse quickened.
Schools had closed 2 days ago, and this was a Gala no one dared to miss.
In the hope that I might just see Adam tonight, and maybe tell him how I really feel.
Perhaps this night might just change everything.