In College, I Bought a Boyfriend

Back in college, I “bought” a boyfriend.
The deal was simple: be with me, and I’d cover his family’s medical bills.
For four years, the brilliant, broke scholar swallowed his pride and stayed by my side.
Then, my family went bankrupt.
When I broke up with him, he was as cold as ever. He didn't say a single word to ask me to stay.
Years later, I was working as a cocktail waitress in a high-end lounge to pay off my debts. He had become a tech mogul, with the former campus belle on his arm.
He asked me, "Do you regret it?"
"No."
"Well, I do."

1
After all these years since graduation, I never imagined I would run into Damian Sterling like this.
As I served the fruit platter, I kept my head down, praying he wouldn't see my face.
Vanessa Croft sat beside him.
The prodigy and the beauty—a perfect match.
"Waitress," Damian called out to me. "Slice the orange."
I turned my back to him, my hands beginning to tremble as I sliced the fruit into neat crescents.
A long time ago, when oranges were my favorite thing in the world, Damian would always cut them for me. He had a surgeon's precision, each slice a perfect, uniform thickness.
Back then, I thought it was a gesture of love.
Only later did I realize it was just a habit. His mind would wander to a thousand different things as he performed the simple task, but never, not once, to me.
Four years. It felt like half a lifetime.
Somehow, the conversation in the private room drifted to college romances.
Someone piped up, "I heard Mr. Sterling had a girlfriend for all four years of college."
My hand faltered.
Damian just hummed in acknowledgment.
"Wow, four years. That’s your entire college experience. How romantic."
Damian didn’t respond, and an awkward silence fell over the group. The guest, trying to fill the void, pressed on, "Four years is a long time. She must have been unforgettable, right?"
The silence stretched, thick and heavy.
After what felt like an eternity, Damian let out a soft, dismissive laugh.
"Hardly."

2
"Honestly, it's a miracle Damian doesn't despise her," Vanessa explained with an effortless grace, saving the conversation.
"Damian and I went to the same university. You have no idea… ugh, I felt so bad for him back then. If his ex hadn't been in the way, do you really think it would have taken us this long to get together?"
"Of course! Vanessa, you're a huge star now. No matter how great his ex was, could she ever compare to you?"
The mood in the room instantly lifted.
I tugged the brim of my cap lower, desperate to just disappear.
The fruit knife slipped, slicing my finger. A sharp hiss of pain escaped my lips, drawing the attention of the table.
"What's wrong with you?" Vanessa complained, her voice sharp with annoyance. "Can't you even cut a piece of fruit?"
"I'm so sorry. I'll get you a fresh platter."
I snatched the plate, ready to flee.
"Wait."
Damian’s voice stopped me in my tracks. Each word was slow, deliberate.
"Turn around."

3
My feet felt nailed to the floor.
One second. Two.
My manager, sensing trouble, rushed over.
"My apologies, everyone. She's new, still learning the ropes. The fruit platters are on the house tonight." She shot me a pointed look. "What are you waiting for? Go get a new one!"
It was the escape I needed.
Later, my manager, a kind woman named Sarah, pulled me aside.
"You need to be quicker on your feet next time," she said gently. "We were all new once. But a complaint from that room, and you'd be working tonight for free."
"Thank you, Sarah."
"Don't mention it. Just be extra careful with the VIP room. They're all heavy hitters, especially the youngest, most handsome one in the middle. He's the founder of a huge tech startup. He's not someone we can afford to cross."
"Sarah… I'm a little shaken up. Could you possibly take the new platter in for me?"
"Sure thing."
I let out a breath I didn't realize I'd been holding.
If there was one person in the world who had already crossed Damian Sterling beyond forgiveness, it had to be me.
I was the ex he was talking about. The one it was a miracle he didn't despise.

4
I still remember him so clearly from our freshman year.
Damian Sterling, standing amongst the sea of new students in his faded, worn-out clothes, a world apart from everyone else. He was visibly poor, but he was also visibly proud, carrying himself with a straight-backed dignity that money couldn't buy.
I loved the cool, quiet timber of his voice. I loved the way his eyelids would lower when he looked at me.
He was desperate for money, but the financial aid he was counting on was snatched away by a legacy student with connections.
So, after a night class, I cornered him, grabbing his hand like a predator.
"Damian, I like you. Be my boyfriend. I'm loaded, we can share my allowance. Hell, I'll even pay you for every kiss if I have to."
Of course, he refused.
But my life up to that point had been a gilded path of yeses. I didn't understand the meaning of defeat. The more he pushed me away, the tighter I clung.
The breaking point came when his grandfather, the man who had raised him, fell critically ill. Without a second thought, I paid the mountain of medical bills.
Damian finally surrendered.
In my blissful ignorance, I thought I'd saved him.
It took me a long time to understand the truth.
I had won him, but in doing so, I had broken his spirit.
Even after we were together, he worked relentlessly, taking on every part-time job he could find to pay for his own expenses. He barely touched my money, but things only got worse.
Whispers started circulating on campus. They said Damian had sold himself for money. His classmates looked at him differently. They gave him ugly nicknames.
I remained hopelessly optimistic and naive. I’d squeeze his hand and say, "Don't listen to them. They're just jealous."
...
I lived in my own ivory tower, completely oblivious to the solitary war Damian was fighting.
Senior year, my family went bankrupt.
I didn't tell him.
I just called him to meet me and said, "Let's break up."
"Why?"
"I'm bored of you."
"Okay."
And just like that, it was over. I imagine he must have been happy, finally free.
The day we broke up, I snapped my SIM card, deleted my social media, and boarded a train to a different city to start working off my family's debt.
I only returned three months ago.
Damian looked like he was doing more than okay. He was always a genius, the kind who made the rest of the department look like children. In just four years, he'd become a tech mogul worthy of a business magazine cover.
And Vanessa Croft, our old campus belle who'd become a celebrity in her junior year... I never expected them to end up together.
Good for them. It's for the best.
I pressed a hand to my chest, forcing down the bitter ache.
At 4 a.m., my shift was finally over. I was the last to leave. A coworker, thinking the building was empty, had already shut off the main lights and the elevators.
I jabbed at the elevator button in frustration, hoping to bring it back to life.
"You should probably call someone."
Damian's voice echoed from the darkness behind me.

5
I froze, then mechanically called my coworker.
The elevator whirred back to life. Damian and I stood in the cramped space, the silence deafening.
"You guys work this late?" he asked, his tone casual.
"We leave after the last guest is gone."
"Is the pay good here?"
"It's alright."
I kept my head down, the cap hiding my face.
He didn't seem to recognize me. He chatted idly for a moment, then glanced at his watch. "This elevator is painfully slow. My girlfriend is probably getting impatient. She's very clingy, you know. Loves to be doted on."
My heart clenched. He was talking about Vanessa.
"What about you?" he continued. "You get off this late, doesn't your boyfriend come pick you up?"
"I live close by."
The elevator dinged. The second the doors opened, I bolted.
But Damian, who had been so calm just moments before, finally snapped.
"What are you running from?" he growled, his voice dangerously low.
"Where do you think you can run to, Elara?"
"Was it fun? Just vanishing off the face of the earth?"

6
Damian advanced on me, closing the distance between us.
He was still the boy from my memories, but the youthful edges had hardened into a restrained, mature intensity.
"New number, deleted accounts… not even our old professors could find you. You’re really something else, Elara."
I slowly lifted my head, meeting his gaze.
"You must have… used your connections to find out, right? That my family went bankrupt, that my father is still buried in debt…"
"Why didn't you tell me?"
I was speechless.
"Was it too much for your pride, Miss Vance? Too embarrassing to admit you'd fallen?"
"No—"
Before I could finish, Vanessa walked over.
"Oh my god? Elara! It really is you!"
She was even more beautiful than in college, polished to perfection from head to toe.
"It's been forever! Everyone from our class has been looking for you. Where have you been for the last four years?"
"I moved down south."
"No wonder," Vanessa said, her eyes scanning my uniform, then landing on my coat with feigned surprise. "Elara, isn't that the down jacket you bought in junior year? The filling is coming out. Are you still wearing this?"
I used to be the kind of person who threw clothes out after one season. Her question was a deliberate jab, meant to humiliate me.
But I was numb to it now.
"It's not broken. It still works."
Vanessa's expression softened into one of pity. "Are you having a hard time? You should have just said something! We're old classmates, we can help."
She pulled a credit card from her purse.
"Here, take this. Don't worry about paying me back."
"Thank you, but I don't need it."
I looked from her to Damian, a quiet smile on my face.
"I'm getting married soon. You should both come."
The words hung in the air. I saw the shock register on Damian’s face, his entire demeanor freezing over.

7
The lounge was just my night job; I had a day job to get to.
On Monday, a major potential client came into the office.
My coworkers were gossiping. "I heard this guy is a genius. Apparently, he created his entire system just to find someone."
"Really? Who?"
"His ex-girlfriend, I think."
A prickle of unease ran down my spine. A very bad feeling.
"Did he find her?"
"No idea. The system isn't even fully launched yet, but investors are pouring money into it. The potential is massive. That's why our boss is so desperate to partner with him."
I gathered the presentation materials.
As I approached the conference room, I heard Damian's voice.
"Regarding the partnership, I'm going to need more time to consider."
I pushed the door open and placed the files on the table.
Damian’s eyes, sharp and intense, locked onto mine. "What are you doing here?"
"I work here."
This was my main job.
My boss looked between us, curious. "Elara, you know Mr. Sterling?"
I chose my words carefully. "We've met."
"Just met?" Damian’s voice was laced with a familiar anger.
What was he so angry about? He was the one who walked away without a second glance when I broke up with him.
He pointed at me. "Mr. Davis, I'll sign the contract on one condition. I want Elara Vance assigned as my project assistant."
My boss agreed instantly, not even giving me a chance to object.
They talked all day.
At five o'clock, I packed my bag to leave.
Damian blocked my path. "Where do you think you're going? I haven't dismissed you."
"Mr. Sterling, I can't work overtime today. I have to be somewhere."
"Where?"
"I have to go deliver for DoorDash."
Damian stared at me, his face a mask of disbelief.

8
I used to be so spoiled I wouldn’t even touch a takeout container.
For four years of college, Damian had been the one delivering food after class. His dinner was often just a free meal box from the delivery company.
I found him once, in a cramped break room, huddled with a group of other couriers, shoveling rice from a flimsy box.
"Damian, why are you eating this? It's not sanitary," I'd said.
He'd looked deeply uncomfortable. "Does it matter?"
"Come on. Let's go get steak."
I dragged him to a new high-end steakhouse where a single meal cost over a hundred dollars. He stood outside for a long time, silently taking off his delivery uniform before stepping inside.
After my family's fall from grace, I finally understood the humiliation he must have felt that day.
Just like I was feeling now.
It started to snow.
The ground was slick, and I wiped out, sending the customer's food spilling across the pavement. I called to explain, but he just screamed at me.
"Stop making excuses! Late is late!"
My scraped palm throbbed in the biting cold, but I ignored it, repeating "I'm sorry" over and over.
Suddenly, Damian was there, lifting my delivery bike.
I don't know how long he'd been watching.
I instinctively hid my injured hand behind my back.
"Don't hide it," he said, his voice hoarse, his eyes rimmed with red. "Go wash it."
"I have to deliver this first."
"Get in the car. I'll take you."
The customer lived on the first floor. When I handed him the remade order, he muttered, "Damn, even people in Porsches are doing DoorDash now?"
I had to get to my next order.
"Stop," Damian said. "Don't do any more deliveries tonight."
"I can't. I haven't made nearly enough."
"Then I'll buy your time."
"What?"
A notification pinged on my phone. A new order, assigned directly by him.
"I'm buying the rest of your night," he said.

9
Damian drove me to his apartment.
I stood in the entryway, refusing to go any further.
"Vanessa will be angry."
"You have time to worry about other people?" he shot back. "Look at yourself. You're a mess."
Besides the scrape on my hand, I was covered in dirty, melted snow.
"And another thing, Elara," he said, gesturing around the pristine, minimalist space. "Does this look like a woman has ever been here?"
"You don't live together?"
"I've never been with her. Not really."
He tossed a contract onto the coffee table.
"She came to me six months ago and proposed a deal. She didn't want to get cornered by sleazy producers, so she asked me to pretend to be her boyfriend. In return, she helps me handle difficult clients." He paused, as if worried I wouldn't understand. "Some clients think the best way to do business is by sending women to my hotel room. It's a headache. Vanessa acts as a buffer."
The contract spelled it out clearly: a professional arrangement, no interference in each other's private lives.
Damian took my hand and began cleaning the wound.
I saw a row of unopened boxes on a shelf. A line of luxury hand creams.
It was the brand I used to love. He had the entire collection.
"I asked your coworkers about you today," he said, his voice low.
"You don't have a boyfriend. You even said you were single at a team dinner last week. Elara, you were lying to me, weren't you?"
"I wasn't."
"Then show me a picture. Of you and this man."
"We haven't taken any."
"You? The girl who documents everything? You don't have a single picture with your new love?"
"Thanks for the reminder. I'll take one next time and send it to you."
A bitter laugh escaped Damian's lips.
He suddenly leaned forward, bracing his hands on the sofa on either side of me, trapping me. The heat from his body radiated through my sweater.
"I bought your time, Elara. You know what that means, don't you?"
"I'll refund you. Damian, I'm serious, I'm getting married."
His hand trailed down my arm, his fingers stopping at my wrist.
"Getting married, but still wearing a bracelet your ex gave you? Doesn't seem right, does it?"

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