Matched with my boss

Chapter 2

Chapter 2

Jake.

"I never thought taking over a family business would include opening a dating app."

After several years spent traveling the world, with my life divided between prestigious university classrooms and snow-capped mountains where I practiced extreme sports, the time had finally come to face my destiny. I knew that sooner or later, I’d have to return to New York and face the inevitable: my father’s financial consulting firm.

I’d always known my future was here, in the glass office at the top of one of the city’s most imposing skyscrapers, but I never imagined it would be so soon. However, my father’s health was deteriorating faster than any of us had anticipated. The man who was once an unstoppable force in the business world now struggled to stand through meetings.

So here I was, in my newly rented apartment, preparing for my first days as acting CEO of Sidle Financial Consulting, the company my father had built from the ground up. Even though I had spent years preparing for this moment, the reality of it all felt overwhelming.

I took a deep breath and looked out the window. The city sparkled below me, full of promise and chaos. It was my turn to prove that everything I had learned hadn’t been in vain.

"Jake, are you listening to me?" my brother’s voice interrupted my thoughts.

I turned to find Ryan, my older brother, looking at me from the kitchen, where he was making coffee. He had arrived with his wife in New York yesterday. They live in Washington, and they decided my place was theirs for a few days, and I’m no one to tell them otherwise.

Anyway, Ryan had always been the more serious of the two of us, the prestigious economist with more degrees than anyone I knew. While I was jumping out of helicopters in the Swiss Alps, he was publishing articles in academic journals.

"Yeah, sorry, I was thinking about tomorrow. The big day," I replied, rubbing the back of my neck. I knew the pressure was catching up to me, but I couldn’t afford to fail.

Ryan came over and set two cups of coffee on the living room table.

"Relax, Jake. It’s not like you’re unprepared for this. You’ve been studying your whole life to take over the company. Besides, Dad trusts you, and if he does, you should too."

I took a sip of coffee and nodded, though deep down, I wasn’t so sure. The only time I had felt truly free was in the mountains, practicing extreme sports, far from family expectations.

"I know, but the company has a reputation to uphold. I can’t afford to mess things up from the start," I responded, placing the cup on the table.

Before Ryan could say anything, Lia, his wife, entered the room. Lia was the complete opposite of Ryan. While he was a prestigious economist with a structured mind, working for the country’s Senate and very close to the president, she was a bohemian artist, a lover of art and organized chaos. She was a hippie at heart, always talking about energies and vibes.

"Good morning, guys!" Lia said, flashing a carefree smile as she lit an herbal cigarette. "Jake, have you thought about what I told you? You’ve got to open yourself up to new experiences!"

"Open up to what, exactly?" I replied, raising an eyebrow.

Lia dropped onto the couch in front of me and exhaled a cloud of smoke. Ryan glanced at her out of the corner of his eye, as he always did, but said nothing. He was used to it by now.

"To a dating app, of course!" Lia said, as if it were the most obvious thing in the world. "Look, Ryan and I met on one of those, and you see how well we’re doing. Total bliss and…"

Ryan cleared his throat, clearly uncomfortable with the direction of the conversation.

"Lia, I don’t think Jake’s interested in that. He has a lot to focus on with the company and all..."

"Nonsense!" Lia interrupted him, clapping her hands in the air. "Do you know how many soulmates you could be missing out on while you’re stuck in that glass office? Jake, you need to open your mind and heart. You never know what might happen."

I chuckled to myself. It was typical of Lia to talk like that. While Ryan talked about interest rates and econometrics, Lia talked about chakras and energies. If it weren’t for the fact that I saw how happy they were together, I would have thought they were completely incompatible.

"I don’t know, Lia. I don’t think a dating app is my thing," I replied, shaking my head.

Lia wasn’t discouraged. She leaned forward as if she were about to reveal a big secret.

"That’s what we all say until we find the right person. Just try it. You’ve got nothing to lose. Besides, now that you’re going to be in a stable place, it’s the perfect time to find love!"

I remained silent, considering her words. I had spent years moving from place to place, focusing on my studies and adventures. I had never had time for a serious relationship. And frankly, I hadn’t felt the need. But now, back in New York, with a more stable life on the horizon, I wondered if Lia might be right.

"Come on, Jake, don’t be so closed off," Ryan finally said. "It’s weird, yeah, but not that bad. I met Lia on one of those apps, and at first, I didn’t think it would work either. Look at us now."

I stared at him. It was hard to imagine my brother, the most serious man I knew, navigating a dating app. But there he was, married to someone completely different from him.

"I can’t believe you’re convincing me to do this," I said, laughing. "But fine, I’ll try it. Only because you’re putting too much pressure on me."

Lia clapped excitedly.

"I knew you’d do it! You’re going to have so much fun!"

Ryan shot me a warning look.

"Just... don’t take it too seriously at first. It’s a weird world out there. But it doesn’t hurt to meet new people."

"We’ll see," I said, pulling my phone out of my pocket.

I couldn’t believe I was doing this. I opened the app store and downloaded the app Lia recommended. I felt ridiculous. What did a dating app have to do with the fact that I was about to take control of one of the most prestigious financial firms in the city?

As I set up my profile, I chose a discreet photo from my last vacation, where I wore my ski goggles and gear. I didn’t want to seem too exposed. I also didn’t want anyone from the company to find it by accident.

"How’s it looking?" Lia asked, leaning over my shoulder.

"Neutral enough," I replied, showing her my profile picture and the bio I had written: "Finance professional. Adventurer. PhD in Financial Economics from the University of Edinburgh. Extreme sports lover."

"Perfect," Lia said, smiling. "Now, just wait for the matches!"

I glanced at the profile again and turned off the screen.

"It’s done," I said. "Now I have to get ready for tomorrow."

I stood up from the couch, ignoring Lia’s laughter as she continued talking about how fate worked in mysterious ways. Ryan gave me a sympathetic look.

"Good luck tomorrow, Jake. You’ll do great."

I nodded, feeling the weight of everything that was coming. The business, the pressure, the responsibility. And now, also, online dating.

"This will be interesting..." I thought as I headed to my room.

I lay down on the bed, letting the mattress embrace me, but before I could switch off my mind, my phone vibrated.

I grabbed it with one hand and opened the dating app. With a sigh, I started swiping through the images of women. Most of them were incredibly beautiful, though some had descriptions that left little to the imagination.

"Just looking for fun. Nothing serious." I read aloud and rolled my eyes. I wasn’t surprised. It certainly wasn’t the first time I’d seen something like that, but it felt exhausting.

I swiped left, discarding profile after profile. Some seemed interesting, but not enough to grab my attention. Others were too direct, almost mechanical, as if they weren’t even looking for a real connection. I was about to close the app when I heard my brother’s voice shouting from the other side of the apartment.

"Jake, Ian’s here!" Ryan always raised his voice as if there weren’t walls between us.

I got up from the bed quickly, leaving the phone on the nightstand. Ian, my best friend since college, had arrived in New York a few weeks ago, looking to break into the publishing world after years of photographing landscapes around the globe. We had met in freshman year, and although we had completely opposite personalities, our friendship was instant.

"Coming!" I shouted back as I threw on a T-shirt and left the room.

When I entered the living room, Ian was there, sitting on the couch with a beer in hand, chatting animatedly with Ryan.

"Jake!" Ian stood up with a wide grin and hugged me tightly. "Man! Took you long enough to come back to the big city."

"Yeah, you know..." I laughed, hugging him back. "Corporate life is calling, whether I like it or not."

Ian had always been the carefree part of our duo. While I obsessed over numbers and responsibilities, he found his freedom through art. But lately, he had decided to leave behind photographing remote landscapes to try something new: the publishing world.

"So, how’s your move to New York going?" I asked as I grabbed a beer from the fridge and sat down in one of the dining chairs.

"Oh, you know, the usual. A bit of chaos here and there, but the fashion agency I’m working for is great. They’ve got me running all over the place, but I enjoy it. New York is the place to be if you want to make it in this business."

Ryan, who never understood much about the art world, looked at him curiously.

"How’s that photographing models thing going?" Ryan asked, as if it were something trivial. "It’s not the same as capturing mountains, is it?"

Ian smiled.

"No, of course not, but it’s a different challenge. There’s something intriguing about working with people, especially when you’re trying to capture a story in a single image. Plus, I won’t lie, being surrounded by models all day has its perks."

"Oh, the perks," I responded sarcastically, taking a swig of my beer.

Ian shrugged.

"You know how I am. I like my space. You offered for me to stay with you, but honestly... well, I prefer my own apartment. That way, I have freedom to... you know."

Ryan laughed, and I smiled too. Ian had always been a womanizer, unable to commit to anyone for long. While Ryan was happily married, Ian enjoyed his single life as much as he could.

And me... I just enjoyed seeing them happy.

"No problem," I replied. "I’m just glad you’re here. It’s good to have a friend around when life starts getting so... complicated."

We fell silent for a moment, and then Ian looked at me curiously.

"So, how’s the company going?" he asked, leaning forward. "Your dad’s going to give you full control, right?"

"Yeah, something like that." I took another sip of beer, feeling the weight of those words. "It’s a big step, Ian. I can’t mess this up. My dad trusts me, and honestly... I can’t let him down."

"You won’t." Ian smiled with that carefree confidence he always had. "But, speaking of big steps, Ryan told me you opened an account on a dating app. Tell me that’s not true."

I laughed, shaking my head.

"Ryan told you that?" I looked at my brother, who smiled and shrugged. "Yeah, Ryan and Lia made me. They didn’t give me much of a choice."

Ian burst out laughing and clapped me on the back.

"Did they really make you do that? You? The man of numbers and finance, looking for love on a dating app. I’ve got to see this!"

Ian reached out, pointing to my phone.

"Come on, show me. I want to see how this thing works."

I shook my head, but it was clear he wasn’t going to let it go. With a sigh, I pulled the phone out of my pocket and opened the app. The notifications were already piling up. As I leaned forward to show it to Ian, he smiled like a kid in a candy store.

"Look at this," I said as I swiped through the profiles. "Nothing out of the ordinary. Some beautiful women, but nothing that really interests me."

We went through several profiles together. Some women were surprisingly direct, looking for "no-strings-attached fun," which wasn’t something I was particularly interested in at the moment.

"And this one?" Ian asked, pointing to a woman who was clearly looking for something casual.

"No." I quickly swiped left, not even thinking twice.

"Come on, Jake. Easy s*x! Doesn’t that sound good?" Ian joked, nudging me.

"I’m not looking for that right now," I replied, ignoring his teasing.

We kept scrolling through profiles until, suddenly, an image caught my attention.

It was a woman with wavy brown hair, lighter at the tips, and intense blue eyes that stood out even on the phone screen. In some photos, she wore glasses, in others, she didn’t. She smiled in all of them, and her smile was warm, with dimples that made her look innocent and friendly, besides being incredibly beautiful. Too beautiful to be true. She had something special. Something that made me stop.

"Wait, wait, this one..." I said, pausing on her profile.

Ian looked over my shoulder and laughed.

"A nerd? Really? After what you just turned down..." he teased, but I was too focused on the description that accompanied the photos.

"Passionate about finance, coffee lover, and professional dreamer."

I stared at the screen, unable to believe what I was seeing.

"A finance professional?" I said quietly, more to myself than to Ian. "I don’t know many women in finance who look like that."

Most of the women I had met in my career were dedicated professionals, but none were as... captivating. There was something about her profile that drew me in. Her bio was witty, and frankly, I found it intriguing to meet someone with similar interests to mine.

"Are you going to like it or not?" Ian asked, nudging me again.

With a smile, I swiped right, liking her profile. To my surprise, it didn’t take a minute for the app to notify me of a match.

"Wow, that was fast," I said, surprised.

"Don’t tell me you just matched with the nerd!" Ian laughed as he took another sip of his beer. "I knew you’d end up with someone who knows more numbers than you."

"Look who’s talking," I replied, rolling my eyes. "At least I’m looking for something more than a one-night stand."

At that moment, the app vibrated again. A message. The same woman, the finance professional, had sent me a message.

I opened it and smiled immediately as I read it.

"Do you know what my favorite kind of relationship is? The one that always offers a good return on investment."

The smile widened on my face as Ian looked at me, curious. He clearly knew, so I quickly typed my response, still smiling, and dared to be a little more direct. Her blue eyes had practically begged me to get to know her better.

"As long as it’s not a high-risk investment... though with you, I think it’s worth the risk."

"What? What did she write?" Ian asked, leaning forward.

"Nothing that concerns you, Ian," I replied, still smiling.

"LOL, I like you"

I felt an immediate connection, as if this woman were different from all the others I had met. And for the first time, I thought that maybe, just maybe, opening that app hadn’t been such a bad idea after all.