I Started a New Job and Discovered My Boss Was My Longtime Rival — Story of the Day

I thought I’d finally caught a break when I landed my dream job. But my excitement quickly turned to dread when I saw who my new boss was—my old college rival, the guy who made my college years miserable. Now I’m stuck working under him, and I’m bracing for the worst.

After three long, frustrating months without a job, there it was—an email sitting in my inbox. It was from the company I’d been dreaming about for years, the one I’d always imagined myself working for. But now that it was real, I just sat there, frozen, staring at the screen.

“How long are you going to wait?” my roommate Shanti asked, giving me one of her classic no-nonsense looks. “You’ve been staring at that screen for ten minutes. Just open it. They definitely accepted you. If they didn’t, they’re idiots.”

I sighed, barely able to meet her eyes. “I’m scared, Shanti. What if it’s a no? My whole future depends on this. I don’t know if I can handle another rejection.”

Shanti rolled her eyes and sat down beside me. “Oli, you’re being dramatic,” she said, grabbing my laptop before I could stop her. Without waiting for me to agree, she clicked on the email. My heart felt like it was going to burst right out of my chest.

“Dear Olive,” she began in a slow, serious tone. “Unfortunately, as you were an excellent candidate…” She paused, and my heart dropped.

“They didn’t hire me?” I muttered, already covering my face with my hands. I didn’t want to hear the rest.

But Shanti kept reading. “You were an excellent candidate, which is why we regret to inform you that you’ll have to sacrifice your personal life, hobbies, and the time you spend cooking for your lovely roommate because now you’ll be spending all your time at work.”

I blinked, lowering my hands. “Wait… what? I got the job?”

Shanti grinned. “I added some flair, but yes, you got the job!”

I sat there in shock for a second before I jumped up, nearly knocking my laptop over. I wrapped my arms around her, laughing.

After a few minutes of celebrating, I pulled away and glanced back at the laptop. Shanti leaned in closer, her eyes glued to the screen with me.

I skimmed through the text until I got to a line that made my heart skip. “…You will be working under Tyler Wilson’s team,” it read. My stomach twisted.

“No, no, no,” I blurted out. “This can’t be happening. Why is this happening to me?”

Shanti looked at me. “Ty Wilson… isn’t that the guy who hated you in college?”

“Yep,” I said, running my hands through my hair. “He really, really hated me.”

“Yikes, that’s awkward,” Shanti said.

I looked at her, desperate. “What am I supposed to do?”

Shanti smiled and nudged me. “You go there, and you show him how amazing you are,” she said.

The morning of my first day felt like a blur. My hands shook, and my stomach churned. Walking into the office, everything felt huge and intimidating, but I pushed through the nerves.

Melanie, the project administrator, greeted me with a bright smile. She led me and three other newcomers into a small conference room. I noticed right away—I was the only woman other than Melanie. Typical, I thought. People still underestimate female mathematicians.

Melanie started explaining the project, our tasks, and who we’d be working under. When she talked about Ty, her tone was warm and positive. It surprised me. Maybe he’d changed since college. Maybe this wouldn’t be as bad as I feared.

“Speak of the devil,” Melanie joked as Ty stepped into the room. I felt my breath catch. He looked even taller than I remembered, still with that same confident stride. And, annoyingly, he was still handsome.

“Welcome, everyone,” he said, giving a quick smile. “I’m glad to have you on my team.” He walked around, shaking hands with each of the new hires. But when he got to me, he just glanced and moved on. No handshake, no greeting. So, he hadn’t changed at all.

“Your equipment has been ordered,” Ty continued. “It should be waiting at your desks… And Olive,” he added, his eyes flicking to my arms, “make sure you follow the company dress code.” He pointed at my tattoos, his tone flat. What a jerk! Before I could respond, his phone rang, and he excused himself, leaving the room.

Melanie later showed me to my desk, where a small, basic laptop sat. “Melanie, I’m sorry,” I said, trying to stay polite. “This laptop won’t work for the tasks I need to do.”

She looked a bit confused. “Oh, I don’t know much about tech,” she admitted. “You should email Tyler. He handles that sort of thing. For now, just settle in.” She smiled kindly before walking away, leaving me with the underpowered laptop.

When I found out I’d be working at this company, I decided to reach out to Ty. I still had his number, which felt odd, but I thought it was worth a shot.

I sent a short, polite message saying I was looking forward to working together, hoping to start off on a friendly note. I waited for a reply, but my phone stayed silent. Not even a “thanks” or “likewise.”

Still, I had to deal with him for work, so I figured email would get a response. I sent my first message, explaining that I needed help with the equipment. I kept it professional and straight to the point.

But the next morning, there was no reply. I tried again, then again. For days, I sent emails, each one getting shorter and a bit more frustrated. Nothing. When I tried to talk to him in person, he’d either walk away or look down at his phone like I wasn’t even there.

One afternoon, I was sitting at my desk, twisting the ring on my finger—a fake wedding band, a habit I’d picked up for some peace of mind in male-dominated spaces.

I stared at my laptop hoping for a response that never came. Finally, I snapped. I got up, marched straight to Ty’s office, and pushed the door open without knocking.

I walked straight into Ty’s office, not caring if I was interrupting him. “Listen,” I said, my voice louder than I meant it to be. “I get that you hate me. Fine. You always have. But we’re working together now, and this can’t go on.”

Ty looked up, surprised. “I don’t hate you. Where did you get that idea?”

I almost laughed. “Seriously? In college, you looked at me like I was dirt. Even the professors noticed. And now, here, you call me out for my tattoos, but I’ve seen you come in wearing a torn T-shirt. Plus, you haven’t replied to a single one of my emails! How am I supposed to do my job?”

Ty remained calm. “I’ve replied to all your emails.”

“No, you haven’t,” I shot back. “I haven’t seen a single response.”

“Have you checked your spam folder?” he asked.

“Do you really think I’m that clueless?” I snapped. “This isn’t about spam. I need a powerful computer to do my work, and I need it now.”

Ty’s eyes softened. “I know. I’m working on it.”

I didn’t buy it. His expression was calm, but it felt like another excuse. I had enough. I called IT myself, demanding answers. They told me Ty had canceled my equipment order. That was the final straw.

I decided to go to upper management. Straight to Michael, the director. I was ready to fight for what I needed, but as I reached the office, I saw the door slightly open. Tyler was already inside, speaking with Michael. Was he trying to get me fired? I leaned closer, trying to catch their words.

“Either you approve the request to order equipment for Olive, or I’ll shut down the project,” Ty said, his tone firm.

Michael sounded annoyed. “Tyler, you don’t understand—”

“No, you don’t understand,” Ty cut him off. “Olive is the best person we’ve hired. Maybe the best in this whole company. You’re letting your own biases get in the way. It’s ridiculous.”

I couldn’t believe what I was hearing. Ty was defending me?

Michael sighed, sounding tired. “Fine. I’ll approve it.”

Ty left Michael’s office, and I quickly turned, trying to disappear down the hall. But it was no use—he saw me. He walked straight toward me and gently took my arm, steering me away from Michael’s door.

“What did you overhear?” he asked.

“Enough,” I said. “So, everything you said in there… was true?”

“Yes. I meant all of it,” he replied. “I think you’re more talented and smarter than most of the people here.”

I blinked, trying to process. “So, you were really trying to get the equipment for me?”

He nodded. “The truth is, Michael’s a decent boss, but he has his issues. He didn’t think you could do the job because you’re a woman. He was looking for any excuse to make things hard for you, maybe even fire you.”

My stomach tightened. “But why did you make the comment about my tattoos?”

Ty’s expression softened. “I just wanted to make sure Michael had no reason to complain. Maybe I handled it wrong. I didn’t mean to single you out.”

“So… you don’t hate me?”

“I never hated you,” he said quietly. “Not in college, not now.”

Ty sighed. “Back in college, I was immature. I had feelings, and I didn’t know how to handle them. So I acted like a jerk. I thought teasing was a way to get your attention.”

He looked directly at me. “I liked you, Olive. I thought you were smart, funny, and different from anyone I knew. But I didn’t know how to show it. When I saw you here, those feelings came back, and I fell into old habits.”

I stared at him. “You know ignoring and teasing doesn’t work in adult life, right?”

He gave an apologetic smile. “I know. I was young and stupid.”

He glanced down at my hand. “Now you’re engaged,” he said, looking at the ring.

I followed his gaze and then laughed. “This?” I held up my hand. “It’s fake. Just costume jewelry. Makes it easier to work around guys in this field.”

“Yeah,” I said, smiling. “No engagement. Just avoiding awkward situations.”

Ty looked almost relieved. “Then, maybe I could make it up to you. How about dinner? As an apology.”

I couldn’t help but smile. “Is this a date?” I asked.

“We’ll see,” a small grin on his lips. “And you’ll get your equipment tomorrow. That’s a promise.”

“Thank you,” I said, feeling lighter. He nodded, and I watched him walk away. After all these years of working with men who were hard to read, Ty was still the one who baffled me the most. But maybe that wasn’t so bad.