I was staring at my phone like it might explode in my hands, the way you stare at a stove when you’re not sure you turned it off. Tyler’s text sat there in smug little bubbles: an address, a reservation time, and the kind of enthusiasm that should’ve been illegal after the age of twenty-five.

Giradano’s. Downtown. 7:00. Table 8. Don’t be late.

Friday evening. 6:15. Thirty minutes until I was supposed to walk into a fancy restaurant and pretend I wasn’t already planning my own escape route.

I stood in front of the bathroom mirror adjusting a tie I didn’t even like, watching my reflection look back at me with the same expression I’d had at the DMV last month: resigned, suspicious, and mildly offended by the concept of “appointments.”

Two years ago, I’d gotten dumped in a spectacular, life-reshaping disaster that left me with one lasting skill: the ability to be alone without feeling lonely. It wasn’t glamorous. It wasn’t inspirational. It was just… quiet. I had routines. I had Saturday mornings that belonged to me. I had dinners where nobody asked why my face looked “serious.” I had a life that didn’t require emotional weather reports.

But Tyler, my older brother and self-appointed director of my love life, treated my solitude like it was a temporary illness. Every family dinner became a stealth campaign. Every phone call took a sharp turn from “How’s work?” to “So have you met anyone?” like he was trying to catch me in a lie.

Two weeks ago at my parents’ house, he had physically blocked the doorway until I agreed to a blind date. He didn’t even make it dramatic. He didn’t yell. He just stood there with that stubborn older-brother posture, arms folded, smiling like he’d already won.

“She’s perfect for you,” he’d said. “Ambitious. Smart. Business. You have so much in common.”

“Tyler,” I’d replied, “half the city works in business.”

He’d waved that off like I’d complained about the weather. “Stop trying to outthink it. Trust me.”

That sentence alone should’ve been enough to make me change my name and move to Wisconsin.

The worst part was that Tyler refused to give me details. No last name. No picture. He claimed photos “ruined the magic of first meetings,” which was the kind of logic people use right before they join a cult or buy a timeshare.

All I had was a first name: Rebecca.

I took a slow breath, loosened the tie one fraction, and stared at my shoes like they were also guilty of something. Everything about this felt wrong. Not just “nervous date wrong.” More like “this is how people end up on true-crime podcasts” wrong.

But backing out would be a disaster. Tyler would never let me live it down. My parents would find out. And my mom… my mom had that particular disappointed look that didn’t shout, didn’t nag, didn’t scold. It simply suggested you had personally lowered the national average of human decency.

So I grabbed my keys and left before I could rethink my own surrender.

Chicago traffic did what Chicago traffic does: it turned my thirty-minute window into a cramped, honking hallway of anxiety. I crawled down Lake Shore Drive while my brain ran a full rehearsal of worst-case scenarios.

What if she was boring?
What if she was aggressively into CrossFit and tried to recruit me mid-appetizer?
What if Tyler’s “perfect” meant “she owns a cat and occasionally reads books,” because his standards were that low?

Tyler had a history of questionable matchmaking. Last year he’d set our cousin up with a guy who spent an entire dinner arguing that deep dish wasn’t pizza. I still remembered the cousin’s face, the haunted stare of someone who’d watched their future evaporate over tomato sauce.

Giradano’s was the kind of place that made you check your bank account before you walked in, just in case the air itself cost forty dollars. Dim lighting. Cloth napkins folded like origami. Waiters in actual suits moving with the smooth confidence of people who had never spilled anything in their lives.

The hostess smiled at me with the patient warmth reserved for men walking into romantic situations against their will.

“I’m meeting someone,” I said, as if that explained why I looked like I was bracing for impact.

She checked her list, nodded, and guided me through the restaurant to a corner table near the windows.

“Table 8,” she said. “Your guest hasn’t arrived yet.”

For a moment, I just stood there like an NPC waiting for instructions. Then I sat, opened the menu, and pretended to read words I’d never order. Something about “black garlic foam” and “chef’s seasonal vision” stared back at me, and I realized I had no idea what I was doing with my life.

I positioned myself facing the entrance. Tyler’s one mercy had been two vague details about Rebecca’s appearance: light brown hair, probably wearing something professional.

That could’ve described half the women in Chicago and all the women in my office building.

At 6:53, the front doors opened again, and my entire body went cold.

Not nervous cold. Not “date jitters” cold. Cold like stepping into a lake before your brain has approved it.

Rebecca Sterling walked in.

For half a second, I tried to bargain with reality. Maybe it wasn’t her. Maybe it was someone who just looked like her, another tall woman with the same sharp cheekbones, the same confident posture, the same ability to make a room seem suddenly organized.

But it was her.

Rebecca Sterling: CEO of Sterling Systems, the company I’d worked at for six months. The woman who ran major meetings with calm precision. The woman whose signature appeared on budgets and strategic plans, whose approval shaped entire departments, whose presence made even senior directors straighten their backs like someone had tightened invisible strings.

She was wearing a burgundy dress I’d never seen her wear at work. Her hair was softer, styled differently than her usual polished corporate look, but there was no mistaking that face.

My first thought was confusion. What was she doing here on a Friday night?

My second thought was hope. Maybe she was meeting someone else. Maybe she’d walk past my table, and I’d watch her disappear into some separate corner of the restaurant like a strange, terrifying coincidence.

Then she stopped at the hostess stand. Said something. The hostess checked her list and pointed.

Directly toward the corner. Directly toward table 8.

Directly toward me.

I started to stand up, chair scraping softly against the floor, already assembling a lie about being at the wrong place, having the wrong reservation, suffering sudden and catastrophic food poisoning. Anything.

But Rebecca was already walking toward me.

Her eyes landed on my face, and I watched her expression change in real time: calm to confused to horror, like she’d opened a meeting agenda and found her own nightmare typed in bullet points.

She stopped at the table.

We stared at each other for five seconds that felt like five hours.

Finally, she spoke. Her voice had that crisp edge it always carried in conference rooms when someone asked a question she didn’t like.

“What are you doing here?”

I stood halfway, immediately regretted it, then stood fully because sitting felt worse.

“I’m meeting someone,” I managed. “I think you might have the wrong table. This is table eight.”

I pointed at the number card like she couldn’t read, like she didn’t run an entire company.

Rebecca pulled out her phone, stared at it, then stared back at me.

“No. I’m definitely at table eight. I’m meeting someone too.”

She turned her screen toward me. A text message glowed there: Table 8 at Giradano’s at 7:00.

My stomach sank so hard I felt it in my spine.

I checked Tyler’s message again. Same table. Same time.

Rebecca blinked slowly, like she was trying to unsee her own life choices. “Wait,” she said, voice lower now. “Who are you meeting?”

My throat went dry. “Someone named Rebecca. My brother set it up. He only gave me a first name.”

Her expression shifted again, from disbelief to mortification.

“I’m meeting someone named Connor,” she said, as if the word tasted strange. “My friend Lauren set it up. She said he works in operations.”

We stood there while the puzzle pieces snapped into place with the violent satisfaction of a trap closing.

“Your friend is Lauren Mitchell?” I asked.

Rebecca nodded stiffly.

“And my brother is Tyler Harrison,” I said.

She nodded again, and we spoke at the exact same time.

“You have got to be kidding me.”

Rebecca sat down hard, like gravity had suddenly gotten personal. She covered her face with one hand. I sat too, because my legs had stopped offering reliable support.

What do you say when you realize you’ve been set up on a blind date with the CEO of your company?

The woman who could fire you.

The woman you’d been carefully professional around because she was intimidating, brilliant, and so far out of your league that the concept of “league” felt like an insult to mathematics.

A waiter appeared, cheerful and oblivious, the way the world always is when you’re having a private crisis.

“Can I start you folks off with some drinks?”

I didn’t hesitate. “Beer. Whatever’s biggest.”

Rebecca didn’t hesitate either. “Red wine. Also biggest.”

The waiter blinked once, picked up on the vibe like a trained professional, and vanished.

Rebecca looked up from behind her hand, cheeks bright red. “I can’t believe this. Tyler knows where I work.”

I felt defensive immediately, like it was my fault my brother had the subtlety of a marching band. “Lauren knows where I work too. Why wouldn’t she tell you?”

Rebecca’s eyes narrowed just a fraction. “You’ve complained about me at work, haven’t you?”

My face heated. “What? No. I mean… not complained exactly.”

“Not complained,” she repeated, tone sharp.

“Maybe mentioned that you’re intimidating,” I admitted.

She crossed her arms. “Intimidating?”

“You are intimidating,” I said before I could stop myself. “You walk into meetings like you’re about to interrogate a suspect.”

Rebecca’s mouth tightened. “You’re the one who never speaks up in meetings and then sends messages afterward questioning decisions.”

I sat up straighter. “Those are clarifying questions. Sometimes the directives aren’t clear.”

We glared at each other like we were in a quarterly review, not a restaurant.

Then the absurdity hit me. Hard.

We were on a blind date. With my CEO. Arguing about workplace communication styles.

Rebecca must’ve felt it too, because she let out a laugh that sounded half hysterical, half exhausted.

“This is a nightmare,” she said. “We can’t go on a date. We don’t even get along.”

I pulled out my phone and texted Tyler with shaking hands.

Seriously? You set me up with my CEO? What were you thinking?

His response came back instantly.

Yes, you’re welcome. She’s amazing. Give it a shot.

I showed Rebecca. She was already texting Lauren, and then she turned her phone toward me.

Lauren had written: You’ve both been single too long. Give it one hour. If it’s terrible, you never have to mention it again.

The waiter returned with our drinks and looked between us like he was considering whether to call security.

Rebecca took a long drink of wine, set the glass down, and exhaled.

“Look,” she said, forcing calm into her voice like she was forcing calm into a spreadsheet. “This is clearly a disaster, but we’re already here. I’m starving. And this reservation would be a waste.”

She paused, then added, “What if we just eat and agree to never speak of this again?”

I should’ve left. I knew I should’ve left. But I pictured Tyler’s smug grin, my mother’s disappointed eyes, the family group chat lighting up like a bonfire.

Also, I was starving too.

“Fine,” I said. “One hour. We eat. We make conversation like adults. Then we go back to normal.”

Rebecca nodded. “Deal. And for the record, I’m only doing this so Lauren stops setting me up on dates.”

We ordered mostly in silence. When the waiter left, I took a breath and said, “So… this is officially the weirdest thing that’s happened to me all year.”

Rebecca’s lips twitched, almost a smile. “Same. And I once got stuck in an elevator with the entire board of directors for three hours. So that’s saying something.”

The first twenty minutes were painful in the specific way two people are painful when they’re trapped together and trying not to acknowledge the trap. We talked about weather. Traffic on Lake Shore Drive. Construction on Michigan Avenue that never ended, like the city had signed a contract with inconvenience.

Rebecca cut her salmon into neat, precise pieces, which somehow made perfect sense. Even her meals looked organized.

I was scraping the bottom of conversational barrels when she surprised me.

“Tyler mentioned you do volunteer work,” she said. “What’s that about?”

Something in my chest loosened. Talking about the community center wasn’t complicated. It didn’t require posture or strategy. It was the one place in my week that felt honest.

“Yeah,” I said. “I teach coding to teenagers at the North Side Community Center. Started about a year ago. A lot of these kids don’t get access to tech education, so we try to fill the gap. Basic programming, web design. Stuff they can build on.”

Rebecca’s face changed. Not the CEO mask. Not the professional smile. Real interest lit up her eyes.

“The North Side Center on Ashland?” she asked.

I nodded. “You know it?”

Her expression shifted into something close to excitement. “I’m on the board of directors. Have been for three years.”

My brain stuttered. “You’re on the board?”

Rebecca nodded, almost shy about it. “We approved additional funding for the technology programs last quarter.”

I stared at her like she’d just revealed a second identity.

“Are you… Sterling?” I asked slowly, because there were donors whose names were said in reverent tones at the center, donors who’d funded the entire equipment upgrade.

Rebecca lifted one shoulder. “Yes.”

We had fifteen new computers because of her. Fifteen computers that had changed how those kids learned, how they saw themselves. I’d never known the CEO who made me sweat through meetings was also the reason a fourteen-year-old named Marcus had built his first website.

“You funded our program,” I said, voice low.

Rebecca shrugged like it was the most obvious thing in the world. “The center does important work. It made sense to invest in it.”

And suddenly, without warning, the conversation stopped feeling like work and started feeling like two human beings discovering each other in a quiet hallway of shared values.

We talked about the kids. I told her about the shy girl who’d made a digital art portfolio that looked like it belonged in a gallery. I told her about Marcus, who acted tough but lit up every time he figured something out. Rebecca asked questions that weren’t performative, questions that showed she actually cared about outcomes, not headlines.

She told me, carefully at first, about growing up in a neighborhood where resources were scarce, where “opportunity” was a word people used like a joke. She described a teacher who’d pushed her, a scholarship that had felt like a door cracking open, and the quiet promise she’d made to herself: if she ever got out, she’d reach back.

This Rebecca didn’t feel intimidating. She felt… grounded. Like a person who knew exactly how hard it was to build something from nothing.

By the time the waiter cleared our plates, I glanced at my watch and blinked.

We’d been there nearly an hour and a half.

When I pointed it out, Rebecca checked her phone, surprised. “I didn’t notice the time.”

“Me neither,” I admitted, and that confession felt strange, because I didn’t like being surprised by my own enjoyment.

She looked at me with something like amusement. “I guess when we’re not talking about budget reports, we’re tolerable.”

I laughed. “You’re way less scary when you’re not lecturing me about efficiency metrics.”

Rebecca grabbed her napkin and tossed it at me, missing by a foot. “I don’t lecture. I provide guidance.”

“Sure,” I said, grinning despite myself.

We split chocolate lava cake because she claimed she couldn’t eat a whole dessert alone and I had a serious weakness for anything chocolate. When we finally walked out to the parking lot, it was 9:30, and I couldn’t remember the last time I’d stayed somewhere that long willingly.

We stood by her car under the glow of a streetlamp, city noise humming around us.

There was an awkward pause, the kind that comes when you’ve shared something real and don’t know how to put it back in the box.

“So,” I said. “This was… better than I expected.”

Rebecca nodded. “Same. Lauren is going to be unbearable when I tell her this didn’t go terribly.”

Then her expression sobered, and I could see her mind clicking into risk-assessment mode.

“But Connor,” she said quietly, “dating someone from work feels like asking for trouble. Especially when I’m your CEO.”

She didn’t say it like a warning. She said it like a confession.

I swallowed. “Yeah. Probably a bad idea.”

And even as I said it, I hated the words.

“Let’s just,” I added, forcing a half-joke, “pretend this never happened. Like a weird fever dream. Table 8 hallucination.”

Rebecca held my gaze for a long second. Something in her face suggested she didn’t want to forget it either.

Then she nodded, composed again. “Good night, Connor.”

“Good night,” I said, and watched her drive away with an uncomfortable ache in my chest that didn’t make sense yet.

Monday hit like a truck.

In the office lobby at 8:45, I saw Rebecca getting coffee. She looked exactly like she always did: professional outfit, hair sleek, posture controlled.

But now I knew what her real smile looked like. Now I knew the difference between polite and genuine, and that knowledge made everything feel off-balance.

She glanced up, met my eyes for half a second, then looked away and walked toward the elevators.

My heart raced like I’d just sprinted through traffic.

The morning meeting was torture. Rebecca ran through quarterly projections with her usual calm authority, and I tried to focus on numbers while my brain replayed laughter, board stories, the way her face had softened when she talked about the community center.

When she asked if anyone had concerns about the timeline, I raised my hand.

I never raised my hand.

“I think operations can meet those goals,” I said carefully, “but we might need additional support during the transition.”

Rebecca studied me, expression unreadable, then nodded. “Reasonable point. Let’s discuss resource allocation after the meeting.”

My colleague James leaned in and whispered, “You okay? You never speak up.”

“I’m fine,” I lied.

I wasn’t fine. I was wired. Hyperaware of every glance, every pause, every moment that might mean something or nothing.

That Saturday, I went to the community center for my coding class like always. I was setting up laptops when the front doors opened and Rebecca walked in carrying a box of new equipment.

We froze again, a mirrored moment, but this time there were teenagers around us like curious satellites.

Marcus, the nosiest kid I’d ever met, spotted her instantly. “Mr. Harrison,” he said loudly, “you know Miss Sterling?”

I forced my voice into casual. “Yeah. She’s on the board. Helps fund the programs.”

Rebecca set the box down and smiled at Marcus. A real smile. Warm. “I was dropping off some tablets for the digital art program.”

Marcus grinned. “He’s here every Saturday. Never misses. One time he came even though he had the flu.”

I wanted to vanish. Rebecca’s eyebrows lifted slightly, impressed.

“That’s dedication,” she said, and looked at me. “Can we talk for a minute? About center business.”

We stepped into the hallway. The sounds of kids booting up laptops drifted behind us.

“I didn’t know you taught on Saturdays,” Rebecca said softly.

“I didn’t know you made deliveries yourself,” I replied. “I thought board members just signed checks and showed up for fundraisers.”

She laughed under her breath. “I like seeing where the money goes. Makes it real.”

Silence stretched. It felt like standing by her car again, both of us holding something we weren’t naming.

Finally, Rebecca said, “I’ve been thinking about Friday night.”

My stomach flipped. “Yeah.”

“I can’t stop,” she admitted. “And I keep wondering if we gave up too fast just because we were scared.”

I exhaled, tension easing into honesty. “I’ve been thinking about it too. Like constantly. Which is making work really weird.”

Rebecca bit her lip, gaze flicking down the hallway to ensure no one was listening. “Same. I zoned out during a conference call yesterday thinking about our conversation on community resources.”

I took a risk. “What if we tried again? Outside of work. Keep it separate. See if there’s something here before we let fear decide.”

She was quiet for a long moment. “The power dynamic still worries me,” she said. “If this goes wrong, it could make your job impossible. I don’t want to put you in that position.”

The fact that she cared about that made my chest tighten.

“What if we set rules?” I asked. “We don’t tell anyone at work. We keep our professional relationship exactly the same. We’re honest with each other. If it starts feeling like a mistake, we stop.”

Rebecca considered, then nodded slowly. “Okay. But we go slow. And if work starts affecting this, or this starts affecting work, you tell me immediately.”

I held out my hand.

“Deal.”

She shook it. Her hand was warm in mine, and the simple contact felt like a door unlocking.

“So,” I said, voice lighter, “does this mean I can take you to dinner again? Like an intentional date this time?”

Rebecca smiled. “Yes. But not Giradano’s. I don’t think I can face that place again for a while.”

The next three weeks felt like being teenagers with careers and calendars. We chose coffee shops on the north side where no one from the office went. We ate lunch at a tiny Vietnamese place forty minutes away because it felt safer to disappear into a neighborhood that didn’t belong to our work world.

We walked the lakefront at night when the city lights smeared across the water and anonymity felt possible. Rebecca was funny in a quiet way that caught me off guard, and sharp in a way that made me feel seen rather than judged. She asked questions about my goals that didn’t sound like performance evaluations. I told her about my failed relationship without giving it too much power, and she listened like she was taking my heart seriously.

We kissed twice, both times careful and sweet, like we were both aware of the thin line we were walking. The first kiss was in the parking lot after dinner, her hand lingering on my sleeve as if she was testing whether it was safe to want things. The second was by the lake when she laughed at something I said, and the laughter softened into quiet, and quiet became the kind of moment you lean into without thinking.

I started to believe Tyler had stumbled into brilliance by accident.

Then everything cracked on a Sunday afternoon in Millennium Park.

I was walking near the Bean, clearing my head, when someone called my name.

“Connor!”

I turned and saw James from work jogging toward me.

My stomach dropped because James was the kind of person who noticed everything and treated gossip like cardio.

“Hey,” he said, catching his breath. “Didn’t expect to see you here. You meeting someone?”

“No,” I said too quickly. “Just walking.”

James nodded, then tilted his head. “I could’ve sworn I just saw Rebecca Sterling over by the Bean. Wearing regular clothes. Wild seeing her outside the office, right?”

My brain slammed into panic mode.

If James had seen Rebecca and now he’d found me, his mind was already drawing lines between dots like he was solving a mystery he didn’t deserve.

“I’ve gotta go,” I muttered, then walked away fast enough to look suspicious.

I texted Rebecca immediately: James saw me here. Said he saw you too. We need to be more careful.

Her reply came back: North Gardens. 5 minutes.

When I found her, she was sitting on a bench, posture tense, eyes fixed on nothing.

“Did he see us together?” she asked.

“No,” I said, sitting beside her but leaving space, the way we’d trained ourselves. “Separately. But he’s going to wonder why we were both here.”

Rebecca covered her face with her hands. “This is exactly what I was worried about.”

Over the next few days, the office felt different. Whispered conversations cut off when I approached. James looked at me like he knew something and was savoring it. Someone asked me if I’d been to any good restaurants lately with a tone that made my skin crawl.

By Thursday, Kevin from accounting pulled me aside and asked bluntly, “Are you dating Rebecca Sterling?”

I denied it, but denial doesn’t erase the look on someone’s face when they’ve already decided.

On Friday after work, I met Rebecca at our usual coffee shop. She looked exhausted, like she’d been carrying a weight with no handles.

“Three people asked me this week if I’m seeing someone from the company,” she said quietly. “I don’t know how they know. But they know.”

She set her cup down harder than necessary. “This is too much, too fast. Everyone’s in our business. I can’t breathe, Connor.”

I reached for her hand, but she pulled back.

“I told you I was worried,” she said, voice tight. “About you. About the company. About every decision being questioned. People will think you’re getting special treatment.”

“We can handle gossip,” I insisted, but I could hear desperation in my own voice.

Rebecca shook her head, eyes shining. “I can’t put you in that position.”

My chest tightened. “So what are you saying?”

Her voice cracked. “I’m saying I need space. Time to figure out if I can do this without destroying everything.”

Two weeks of silence followed.

And it was brutal in a way I hadn’t predicted.

At work, Rebecca became cold professionalism again. She didn’t look at me. She didn’t pause near my desk. Her smiles were polite, not real, and I could tell the difference every time, which made it worse.

I threw myself into work, but the harder I worked, the more everything reminded me of her. My team noticed I was snapping at small mistakes. Kevin told me, gently, that I seemed off.

“I’m fine,” I lied again, becoming a person who lied too easily.

Then on Friday afternoon, my phone buzzed with an email that made my blood run cold.

Subject: Immediate audit required.

Corporate headquarters was launching a full investigation into departmental spending in operations, effective immediately. Someone had flagged irregularities in our budget reports from the past six months. They wanted every receipt, every invoice, every approval form.

I stared at the screen as nausea crawled up my throat.

I’d been in my role for six months. Many vendor relationships were set up before I arrived, but my signature was on approvals. My signature meant my responsibility.

By Monday, two executives from corporate sat in our conference room like judge and jury. One was a stern woman named Patricia who asked questions like she was peeling paint off a wall.

“Can you explain why these vendor invoices don’t match the purchase orders?” she asked, tapping the papers.

I pulled up records, staring at numbers that made no sense. She was right. The amounts were different. Not huge, but enough to trigger suspicion.

“I approved what the previous manager set up,” I said. “I took over shortly after.”

Patricia’s expression didn’t change. “You signed off. That makes you responsible.”

By Tuesday, the word “suspension” floated into conversation like a poison cloud. By Wednesday, I was sitting alone in my office staring at spreadsheets that suddenly looked like enemies.

At 3:00 p.m., there was a knock on my door.

I looked up and saw Rebecca standing there with her tablet, expression focused and urgent.

“Can I come in?” she asked. “I think I found something about the audit.”

I nodded, too stunned to do anything else.

She closed the door and sat across from me, tapping her screen until a series of reports appeared.

“I went through system logs,” she said. “I didn’t have to, but I couldn’t stop thinking about it. There was a vendor payment system error back in August, right before you took over. The system processed payments twice for certain invoices but only recorded them once in budget reports. So it looks like discrepancies, but it’s a software glitch.”

I stared at the screen. Relief slammed through me so fast it almost hurt.

“You dug through months of logs?” I asked, voice rough. “Rebecca… after everything…”

She finally met my eyes, really met them, the way she hadn’t in weeks.

“I did it because it was the right thing,” she said quietly, “and because I know you care about doing your job correctly. Even when we disagree.”

Her words hit me harder than the audit ever could.

“I wasn’t going to let corporate blame you for a system error,” she added.

I forwarded the information to Patricia immediately. Within an hour, corporate backed off. They confirmed Rebecca’s findings and admitted the audit had been triggered by automated flags that didn’t account for the glitch.

By end of day, they were apologizing for the disruption and promising a system fix.

When my hands stopped shaking, I went looking for Rebecca and found her in the third-floor break room making tea.

“Hey,” I said.

She turned, guarded. “Hey.”

I kept distance, because habits don’t die quickly. “I wanted to thank you. You saved my job. My team. You didn’t have to do that.”

Rebecca set her mug down. “You didn’t make me uncomfortable, Connor. I made myself uncomfortable.”

She exhaled like she’d been holding her breath for two weeks.

“I panicked,” she admitted. “Everyone being in our business scared me. But these past two weeks were terrible. Walking away didn’t make me feel better. It just made me miss you.”

My chest did something complicated.

“I missed you too,” I said. “An embarrassing amount.”

Her eyes filled, and she didn’t hide it this time. “I was falling for you,” she whispered. “That’s why it scared me. If it was casual, gossip wouldn’t matter. But it wasn’t casual.”

“It wasn’t casual for me either,” I said, stepping closer. “That’s why this felt awful.”

We stood there in the break room with the hum of vending machines and fluorescent lights, and somehow it still felt like the most honest place in the world.

“So what do we do now?” she asked, voice soft but steady.

I thought about hiding and fear and the way secrecy had turned love into stress.

“What if we stop hiding?” I said. “We do it right. We disclose it to HR. We follow whatever rules we need to follow. People will talk, but they’ll talk about something else eventually. And if anyone questions your integrity or my work, we handle it with transparency.”

Rebecca stared at me, then her face shifted into something like relief.

Her real smile appeared, small at first, then fuller. “I’m tired of being scared,” she said. “Let’s try.”

We filed the paperwork. We documented that there was no direct reporting structure. Rebecca insisted any decisions impacting my department go through additional approval channels to remove even the appearance of favoritism. It was careful, responsible, and strangely romantic, because it meant she was protecting both of us with intention.

Tyler and Lauren were, as predicted, unbearable.

Tyler called three times in one day just to say “I told you so” in different formats.

Lauren sent a text that simply read: You’re welcome.

When I brought Rebecca to Sunday dinner, my parents reacted like they’d won a prize they hadn’t bought a ticket for. My mom hugged her like she’d been waiting for this moment her entire life. My dad launched into embarrassing stories about my childhood with the reckless joy of a man who loved mortifying his children.

Rebecca handled it with warmth and humor, asking my parents questions that made them feel seen. Watching her in my family’s living room, laughing in a space where she didn’t have to be the CEO, I felt something settle in me: the sense that this wasn’t a thrilling accident anymore. It was becoming real.

The office gossip lasted about two weeks before people moved on to their next obsession. A few colleagues made comments. A few looked skeptical. Most simply shrugged and returned to their own lives, because adults are surprisingly capable of forgetting drama when deadlines exist.

Kevin admitted, “You two actually make sense,” which felt like a stamp of approval from the most practical person I knew.

Rebecca and I still had hard moments. The power dynamic didn’t disappear; it had to be managed like a sensitive instrument. We learned to communicate better than we did at table eight. We had our first real fight a month in about equipment scheduling and process boundaries, and for a terrifying moment I wondered if conflict meant collapse.

But we didn’t collapse.

We sat down, listened, admitted where we were defensive, negotiated a compromise that respected both autonomy and structure. I realized something important: disagreement didn’t mean love was failing. It meant love was learning.

Three months after our disaster first date, I suggested we go back to Giradano’s.

Rebecca looked at me like I’d suggested skydiving without a parachute, but then she laughed and agreed when I said I wanted to replace the bad memory with a good one.

We sat at table eight again.

Halfway through the meal, Rebecca started laughing. “Remember when you thought I was going to steal your table?”

“I thought you were the last person on earth I’d ever want to have dinner with,” I admitted. “I was so wrong it’s embarrassing.”

Rebecca reached across the table and took my hand. Her fingers were warm, steady. “And now?”

I squeezed gently. “Now you’re the person I want to have dinner with every night.”

We split chocolate lava cake again because some rituals deserve repetition.

Six months in, I brought her back one more time, but this time I’d coordinated with the staff, timed everything, planned details the way I’d never planned anything in my life. The ring sat in a small box in my pocket, heavier than its size, like it carried every moment that led to it.

Dessert arrived. Chocolate cake. And beside it, a small box.

Rebecca stared at the box, then at me, eyes wide.

I stood, heart pounding so loudly it felt like the restaurant could hear it. I knelt beside the table, the world narrowing to her face.

“Rebecca,” I said, voice shaking, “I spent six months thinking you were intimidating and out of my league. Then I spent one dinner realizing you were funny and kind and nothing like what I assumed.”

Her eyes shimmered.

“And I’ve spent the last six months falling completely in love with you,” I continued. “You make me want to be better. You challenge me. You believe in the same things I believe in. And I don’t want to spend another day without knowing you’re in my life.”

I opened the box. The ring caught the light.

“Will you marry me?”

Rebecca’s tears spilled, unguarded, honest. She nodded so fast it made me laugh through my own nerves.

“Yes,” she whispered. “Yes. Of course. Yes.”

I slipped the ring onto her finger and she pulled me up and kissed me right there in the middle of the restaurant while other diners applauded, because Chicago may be busy but it still knows how to celebrate a moment.

Rebecca stared at her hand like she couldn’t believe it was real.

“I can’t believe you proposed at the place where we had our disaster first date,” she said, laughing through tears.

“It felt right,” I said. “This is where it started. Where I learned that sometimes the person you’re trying to avoid is the person you actually need.”

We finished dessert, hands intertwined like we were anchoring each other to the present.

And when we walked out into the city night, Rebecca’s grip tightened around my hand, not out of fear this time, but out of certainty.

I thought about how close I’d come to backing out, to faking food poisoning, to letting intimidation decide my future. I thought about how easy it is to reduce people to titles, to assume a CEO is only sharp edges and deadlines, to assume a quiet employee is only hesitation and compliance.

Sometimes love shows up disguised as the person who makes you nervous, the person you misunderstand, the person you argue with because you’re both used to protecting yourselves.

And sometimes the worst blind date of your life becomes the best decision you ever made, simply because you stayed long enough to see the person behind the mask.

THE END