I Tried to Avoid My CEO —Turns Out She Is My Blind Date
I was staring at my phone like it might explode in my hands. My brother Tyler had just sent me the address to some fancy restaurant in downtown Chicago, and I was about 5 seconds away from faking food poisoning to get out of this whole thing. It was Friday evening, 6:15, and I had exactly 30 minutes before I was supposed to meet a complete stranger for a blind date that Tyler had been pushing on me for three solid months. He wouldn’t shut up about it.
Every family dinner, every phone call, every text conversation somehow circled back to how I needed to get back out there and start dating again. My last relationship had ended two years ago in a disaster that left me perfectly happy being alone. Thank you very much. But Tyler didn’t see it that way. He cornered me at mom and dad’s house 2 weeks ago and literally stood in front of the door until I agreed to the setup.
He kept saying she was perfect for me, that we had so much in common, that she was ambitious and smart and worked in business. I pointed out that working in business was basically half the population of Chicago, but he just waved me off like I was being difficult. What made this whole situation worse was that I had no idea who this woman actually was.
Tyler refused to give me her last name, wouldn’t show me a picture, and only told me her first name was Rebecca. He said photos ruined the magic of first meetings, which I thought was absolute garbage, but he insisted. So, here I was getting ready to meet a mystery woman based on nothing but my brother’s terrible judgment and the fact that her name was Rebecca.
I looked at myself in the mirror and wondered what I was doing with my life. My tie felt too tight. My shoes felt uncomfortable. Everything about this felt wrong. But I knew if I backed out now, Tyler would never let me hear the end of it. mom would get involved. And that was even worse because she had this way of looking at you with disappointed eyes that made you feel like you’d personally ruined her day.
I grabbed my keys and headed out the door. Driving through Chicago traffic while my brain ran through every possible disaster scenario. What if she was boring? What if we had nothing to talk about? What if Tyler had completely misjudged what kind of person I’d actually get along with? He had a history of these setups going terribly. Last year he tried to set our cousin up with someone and they spent the entire dinner arguing about whether Chicago deep dish was actually pizza.
It was brutal to watch. Gordanos was the kind of place that made you check your bank account before you walked in. Dim lighting, cloth napkins, waiters in actual suits. I felt out of place the second I stepped through the door. The hostess smiled at me like she’d seen a thousand nervous guys walk through those doors.
And I told her I was meeting someone. She checked her list and nodded, then led me through the restaurant to a corner table near the windows. Table 8. She said my date hadn’t arrived yet, which gave me about 3 minutes to sit there and panic quietly while pretending to look at the menu. I faced the door because I wanted to see this Rebecca person before she saw me.
Tyler had given me exactly two pieces of information about what she looked like. Light brown hair, probably wearing something professional. That was it. That could be literally anyone. At 6:53, a woman walked through the front entrance and I felt my entire body go cold. Not cold like nervous cold. Cold like, “Oh no, this cannot be happening cold.
” Because the woman who just walked in was Rebecca Sterling. My boss, well, not my direct boss, but the CEO of the entire company where I worked. The woman who ran every major meeting I’d ever sat in. the woman who had reviewed my performance evaluations and signed off on departmental budgets and made decisions that affected hundreds of employees.
She was wearing a burgundy dress I’d never seen her wear to the office. And her hair was styled differently than her usual professional look, but it was definitely her. There was no mistaking Rebecca Sterling. My first thought was pure confusion. What was she doing here? This restaurant was nowhere near the office and it was Friday evening.
Maybe she was meeting someone for a business dinner. Maybe this was just a weird coincidence and she’d walk right past my table and sit somewhere else. But then I watched her stop near the hostess stand and say something and the hostess checked her list and pointed directly toward the corner of the restaurant, directly toward table 8, directly toward me.
My second thought was that I needed to leave immediately. I started to stand up, planning some excuse about being at the wrong restaurant or having the wrong date, but it was too late. Rebecca was already walking toward the table, and her eyes landed on me, and I watched her face shift from calm to confused to something that looked like horror.
She stopped next to the table and just stared at me. I stared back. Neither ofus said anything for at least 5 seconds, which felt like 5 hours. Finally, she said, “What are you doing here?” Her voice had that edge it always had at work when something unexpected happened during a presentation. I stood up halfway, which felt awkward, but sitting felt worse. I’m meeting someone.
I managed to say, “I think you might have the wrong table. This is table 8.” I pointed at the little number card on the table like she couldn’t read. Rebecca pulled out her phone and looked at it, then looked back at me. No, I’m definitely at table 8. I’m meeting someone, too. My friend Lauren set this up.
She showed me her screen and I could see a text that very clearly said, “Table 8 at Girardanos at 7:00.” I pulled out my own phone and checked Tyler’s message. Table 8 at Gardanos at 7. We both stood there staring at our phones, and I felt this horrible sinking feeling start in my stomach. “Wait,” Rebecca said slowly, and her face was starting to turn red.
Who are you meeting? My throat went completely dry. Someone named Rebecca. My brother said it up. He only gave me a first name. I watched Rebecca’s expression shift from confused to absolutely mortified. I’m meeting someone named. She paused and took a breath. Someone named Connor. My friend Lauren said it up.
She said he works in operations. We both just stood there while the pieces clicked together in the worst possible way. I said, “Your friend is Lauren Mitchell?” Rebecca nodded. “Your brother is Tyler Harrison.” I nodded. Then we both said at exactly the same time, “You have got to be kidding me.” Rebecca sat down hard in the chair across from me and put her hand over her face.
I sat back down because my legs felt like they might give out. For about 30 seconds, neither of us said a single word. What do you even say when you realize you’ve been set up on a blind date with the CEO of your company? The woman who literally has the power to fire you. The woman you’ve been carefully professional around for 6 months because she’s intimidating and successful and way out of your league in every possible way.
A waiter appeared looking cheerful and completely unaware of the crisis happening at table 8. Can I start you folks off with some drinks? I said, “Beer, whatever you have, the biggest one.” Rebecca said, “Wine red. Also, the biggest one.” The waiter picked up on the vibe immediately and disappeared fast.
Rebecca looked up from her hands and her cheeks were bright red. I can’t believe this. Tyler knows where I work. I felt defensive immediately. Lauren knows where I work, too. Why wouldn’t she tell you? Rebecca’s eyes narrowed just a little. You’ve complained about me at work, haven’t you? I felt my face get hot.
What? No, I mean not complained exactly. Maybe mentioned that you’re kind of intimidating. She crossed her arms. Intimidating? You’re the one who never speaks up in meetings and then sends these messages later, questioning decisions. I sat up straighter. Those aren’t passive. Those are clarifying questions because sometimes the directives aren’t clear.
We glared at each other for a second and then I realized how ridiculous this was. We were arguing at a restaurant about work stuff during what was supposed to be a date. Rebecca must have realized it at the same time because she let out this laugh that sounded kind of hysterical. This is a nightmare. We can’t go on a date. We don’t even get along.
I pulled out my phone and texted Tyler immediately. Seriously? You set me up with my CEO? What were you thinking? His response came back almost instantly. Yes, you’re welcome. She’s amazing. Just give it a shot. I showed Rebecca my screen. She was texting Lauren at the same time and turned her phone toward me.
Lauren had written, “You’ve both been single too long. Give it 1 hour. If it’s terrible, you never have to mention it again.” The waiter came back with our drinks and asked if we needed more time with the menu. I said yes because I still hadn’t processed any of this. Rebecca took a long drink of her wine and then set the glass down with a sigh.
Look, this is clearly a disaster, but we’re already here and I’m starving and it would be a waste of a reservation. What if we just eat and then agree to never speak of this again? I considered this while drinking my beer. You want to have dinner together? We can barely get through a quarterly review without you pointing out everything my department did wrong. her jaw tightened.
Because your department doesn’t always follow protocol. But fine, if you’d rather leave and deal with Tyler asking why you bailed, I’ll understand. She was right about Tyler. He would absolutely grill me if I left. My parents would somehow find out and then I’d have to deal with mom’s disappointed face, which was worse than any lecture. Fine, I said.
1 hour we eat. We make conversation like adults and then we go back to normal where we pretend this never happened. Rebecca nodded. Deal. And for the record, I’monly doing this so Lauren stops setting me up on dates. We ordered food mostly in silence. When the waiter left, I said, “So, this is officially the weirdest thing that’s happened to me all year.
” Rebecca actually smiled just a little. 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 20 minutes of dinner were painful in that special way where two people are trapped at a table together trying to make conversation about anything except the obvious fact that they’d rather be anywhere else.
We talked about weather, traffic on Lake Shore Drive, the construction on Michigan Avenue that never seemed to end. I found myself scraping the bottom of the barrel for topics that wouldn’t lead to work talk or awkward silence. Rebecca had ordered salmon and was cutting it into neat little pieces, which didn’t surprise me at all because of course she approached food the same way she approached quarterly reports with unnecessary attention to detail.
We’d run out of traffic complaints when Rebecca surprised me by asking, “So Tyler mentioned you do volunteer work. What’s that about?” I felt myself relax a little because talking about the community center was easy. It was the one part of my life outside of work that actually mattered to me. Yeah, I teach coding classes to teenagers at the North Side Community Center.
Started about a year ago. These kids don’t always have access to technology education at school. So, we try to fill that gap, teach them basic programming, web design, that kind of stuff. Rebecca’s whole face changed when I talked about the program. She leaned forward with actual interest. Wait. The North Side Center on Ashland. I nodded.
You know it. Her expression went from interested to almost excited. I’m on the board of directors. I have been for 3 years. We just approved additional funding for the technology programs last quarter. I felt my brain stutter to a stop. You’re on the board. Are you are sterling the donor who funded our entire equipment upgrade? Rebecca nodded.
We needed to make sure the center had proper resources. Those kids deserve the same opportunities as anyone else. I just stared at her for a second because this didn’t match up with the Rebecca Sterling I knew from work. The woman who ran meetings with military timing and sent emails at 6:00 in the morning. You funded our program.
We have 15 new computers because of you. I had no idea. She shrugged like it wasn’t a big deal. The center does important work. It made sense to invest in it. We started talking about the community center and suddenly the conversation flowed. Rebecca told me about how she got involved with the board, how she grew up in a neighborhood without many resources and understood what it meant to have someone invest in your potential.
I told her about some of the kids in my classes, how rewarding it was to watch them discover they could build something from nothing but code and creativity. She asked questions about the curriculum, made suggestions about potential partnerships with local tech companies, and I found myself actually enjoying talking to her.
This version of Rebecca was warm and engaged and nothing like the intimidating CEO who made me nervous during presentations. 40 minutes went by without me noticing. The waiter cleared our plates and asked about dessert. I looked at my watch and realized we’d been sitting there for almost an hour and a half, which was way longer than the 1 hour we’d agreed to.
When I pointed that out, Rebecca looked surprised and checked her own phone. I didn’t even notice the time. She looked at me with something that might have been amusement. I guess when we’re not talking about budget reports, we’re actually tolerable to each other. I laughed. Yeah, turns out you’re way less scary when you’re not lecturing me about departmental efficiency metrics.
Rebecca threw her napkin at me across the table. I don’t lecture, I provide guidance. There’s a difference. We ended up splitting chocolate lava cake because Rebecca said she couldn’t eat a whole dessert alone and I had a serious weakness for anything chocolate. By the time we paid the bill and walked out to the parking lot, it was almost 9:30 and I couldn’t remember the last time I’d willingly stayed somewhere that long.
We stood by Rebecca’s car and there was this awkward moment where neither of us knew what to say. Finally, I said, “So, this was way better than I expected. I’m kind of annoyed at Tyler for ambushing us, but also he might have been right about us having stuff in common.” Rebecca nodded. Same.
Lauren is going to be completely insufferable when I tell her this didn’t go terribly. She paused and looked at me directly, but Connor, dating someone from work feels like asking for trouble, especially when I’m your CEO. The power dynamic alone makes this complicated. I knew she was right, but something about the way she said itmade me think she was trying to convince herself more than me.
Yeah, probably a bad idea. Let’s just go back to how things were and pretend this was some weird fever dream. Rebecca looked at me for a long moment. And I could see something in her expression that made me think she didn’t actually want to pretend anything, but she nodded right back to normal. We said good night and I watched her drive away wondering if I just made a huge mistake.
Monday hit me like a truck and suddenly every single interaction with Rebecca felt loaded with meaning I couldn’t ignore. I walked into the office building at 8:45 like I did every morning. But this time when I saw her in the lobby getting coffee, my brain shortcircuited. She was wearing her usual work clothes, hairstyled professionally, and she looked exactly like she always did.
Except now I knew what she looked like when she smiled for real instead of that polite professional smile she gave everyone at the office. She glanced up, saw me, and for half a second, our eyes met before she looked away and walked toward the elevators. My heart was racing like I just run a marathon. This was ridiculous.
We’d agreed to forget the whole thing happened. We were going back to normal, except nothing felt normal anymore. The morning meeting was torture. Rebecca ran through quarterly projections like she always did, confident and in control. and I sat there trying to focus on the numbers while my brain kept replaying dinner conversations.
When she asked if anyone had concerns about the timeline, I actually raised my hand, which I never did. I think the operations team can meet those goals, but we might need additional support during the transition period. Rebecca looked at me with this expression I couldn’t read. That’s a reasonable point.
Let’s discuss resource allocation after this meeting. My colleague James leaned over and whispered, “You okay? You never speak up in these meetings.” I told him I was fine, but I wasn’t fine. I was hyper aware of every word Rebecca said. Every time she looked in my direction, every moment that felt different from before. That Saturday, I showed up at the community center for my usual coding class with the teenagers.
I was setting up laptops when Rebecca walked in through the main doors carrying a box of new equipment. I froze. She froze. We just stood there staring at each other while a dozen teenagers milled around waiting for class to start. One of my students, a kid named Marcus, who never missed an opportunity to be nosy, said, “Mr.
Harrison, you know Miss Sterling?” I tried to sound casual. “Yeah, she’s on the board here. Helps fund the programs.” Rebecca sat down the box and said, “I was dropping off some new tablets for the digital art program. Didn’t realize you’d be here today. Marcus grinned. He’s here every Saturday. Never misses a class. One time he came even though he had the flu.
I wanted to disappear into the floor. Rebecca smiled at Marcus. That’s dedication. She looked at me. Can we talk for a minute about center business? We stepped into the hallway while the kids set up their workstations. Rebecca spoke quietly. I didn’t know you taught on Saturdays. I usually come by on Friday evenings when the building is empty. I shoved my hands in my pockets.
I didn’t know you made deliveries yourself. Thought board members just sign checks and showed up for fundraisers. She actually laughed at that. I like seeing where the money goes. Makes it real. We stood there in the hallway and it felt exactly like standing in that parking lot after dinner.
like we were both thinking the same thing, but neither of us wanted to say it first. Finally, Rebecca said, “I’ve been thinking about Friday night.” My stomach flipped. “Yeah.” She looked down the hallway to make sure no one was listening. I can’t stop thinking about it, actually. And I keep wondering if maybe we gave up too fast just because we were scared of the work situation.
I felt my pulse speed up. I’ve been thinking about it too, like constantly, which is making work really weird because I keep getting distracted during meetings. Rebecca bit her lip. Same. I zoned out during a conference call yesterday thinking about that conversation we had about community resources. I took a chance.
What if we tried again? Not at work, obviously, but outside of work. Keep it completely separate. see if there’s actually something here before we worry about all the complicated stuff. Rebecca was quiet for a long moment. The power dynamic still worries me. If this goes wrong, it could make your job impossible.
I don’t want to put you in that position. I appreciated that she was thinking about it. What if we set rules? We don’t tell anyone at work. We keep our professional relationship exactly the same, and we’re completely honest with each other. If it starts feeling like a mistake, we stop. She thought about it while voices drifted from the classroom. Okay.
But we take it really slow. And if at any pointyou feel like the work situation is affecting this or this is affecting your work, you tell me immediately. I stuck out my hand. Deal. She shook it and her hand was warm in mine. So, does this mean I can take you to dinner again? Like an actual intentional date this time? Rebecca smiled.
Yeah, but not Gerard Danos. I don’t think I can face that place again for a while. Three weeks went by and we fell into this pattern that felt like we were teenagers sneaking around. Coffee shops on the north side where no one from the office went. Lunch at this tiny Vietnamese place in a neighborhood 40 minutes away. Evening walks along the lakefront when it was dark enough that we probably wouldn’t run into anyone we knew.
I found myself looking forward to seeing Rebecca in a way that had nothing to do with quarterly reports or departmental meetings. She was funny in this quiet, clever way that caught me off guard. She’d make these observations about people or situations that were so accurate it was almost unsettling. And she actually listened when I talked about the stress of trying to move up in a company where everyone seemed more qualified than me.
She didn’t try to fix everything or tell me what to do. She just listened and asked questions that made me think differently about the problems. We’d only kissed twice and both times had been careful and sweet, like we were both scared of moving too fast and ruining whatever this was. The first time was after dinner at that Vietnamese place in the parking lot next to her car.
The second time was during a walk by the lake when she’d said something that made me laugh and then we just looked at each other and it felt natural to lean in. I was starting to think maybe Tyler had actually gotten something right for once in his life. Everything fell apart on a Sunday afternoon. I was walking through Millennium Park just clearing my head and enjoying the weather when I heard someone call my name.
I turned around and saw James from work jogging toward me. My stomach dropped because James was exactly the kind of person who noticed everything and told everyone. He caught up to me breathing hard. Hey, didn’t expect to see you here. You meeting someone? I tried to sound casual. No, just walking, getting some exercise. James nodded toward the path behind him.
I could have sworn I just saw Rebecca Sterling over by the bean sculpture wearing regular clothes, not work stuff. Wild seeing her outside the office, right? My brain went into panic mode. Rebecca was here in the same park where James had just seen her. And now James was looking at me with this curious expression that meant he was putting pieces together.
I said something about needing to get going and walked away fast. Pulling out my phone to text Rebecca. James from work just saw me at Millennium Park. Said he saw you here too. We need to be more careful. Her response came back immediately. Meet me at the North Gardens in 5 minutes. When I found her, she was sitting on a bench looking stressed in a way I hadn’t seen since our disaster first date.
I sat down next to her, making sure to keep a professional amount of distance between us. Did James see us together? I shook my head. No, he saw us separately, but he’s going to wonder why we were both here on a Sunday. Rebecca put her face in her hands. This is exactly what I was worried about.
We’ve been so careful and it only took 3 weeks for someone to almost catch us. Over the next few days, I started noticing things at work. People whispering when I walked by. James giving me these knowing looks during meetings. Someone asked me if I’d been to any good restaurants lately, and the way they said it felt loaded. By Thursday, my friend Kevin from accounting pulled me aside and asked directly, “Are you dating Rebecca Sterling?” I denied it, but I could tell he didn’t believe me.
That Friday after work, I met Rebecca at our usual coffee shop, and she looked exhausted. Three people asked me this week if I was seeing someone from the company. I don’t know how they know, but they know. She set down her coffee cup harder than necessary. This is too much, too fast. Everyone’s in our business. People at work are gossiping.
I can’t breathe, Connor. I tried to take her hand, but she pulled back. I told you I was worried about this, about everything getting tangled up. And now it’s exactly what I was afraid of. I felt my chest tighten. Rebecca, come on. We can handle some gossip. We just keep doing what we’re doing. But she shook her head and I could see tears in her eyes.
I don’t know if I can. This affects your career. People are going to think you’re getting special treatment. They’re going to question every decision I make regarding your department. I can’t put you in that position. I felt desperate. So, what are you saying? She looked at me and her voice cracked.
I’m saying I need space to figure out if I can actually do this. I’m sorry. I just need some time. 2weeks of silence felt like the longest stretch of my entire life. Going back to cold professionalism with Rebecca at work was brutal in a way I hadn’t expected. Now I knew what her actual smile looked like versus her polite work smile, and I could tell the difference every single time she walked past me in the hallway without making eye contact.
I threw myself into work, trying not to think about how much I missed texting her random observations throughout the day. My team noticed I was crankier than usual. Kevin mentioned I’d been snapping at people over small mistakes, which wasn’t like me. I knew I was being difficult, but I couldn’t seem to stop.
Everything reminded me of Rebecca. The community center reminded me of our conversation about helping kids. The coffee shop near the office reminded me of our first intentional date. Even quarterly reports reminded me of her because I kept wondering what she’d think about my analysis. Friday afternoon, my phone buzzed with an email from corporate headquarters.
Subject line read, “Immediate audit required.” My stomach dropped as I read through the message. They were launching a full investigation into departmental spending in operations effective immediately. Someone had flagged irregularities in our budget reports from the past 6 months and they wanted every receipt, every invoice, every approval form reviewed. I felt sick.
My department handled hundreds of transactions every month. If there was an error somewhere, it could look really bad. By Monday, two executives from corporate were sitting in our conference room going through files. They asked me questions about purchases I barely remembered approving. They wanted explanations for expenses that seemed completely normal to me, but apparently looked suspicious to them.
One of them, a stern woman named Patricia, kept asking about a series of equipment purchases back in September. These were approved by you, but the vendor invoices don’t match the purchase orders. Can you explain that? I pulled up my records and stared at the numbers. She was right. The amounts were different.
Not by much, but enough to matter. I tried to explain that I’d approved what the previous operations manager had set up before I took over the role. But Patricia wasn’t buying it. You signed off on these purchases. That makes you responsible for the discrepancies. By Tuesday afternoon, they were talking about formal writeups, maybe suspension, possibly termination if they found evidence of intentional misreporting.
I sat in my office staring at spreadsheets that made no sense, trying to figure out where these errors came from. I’d only been in this position for 6 months. Most of these vendor relationships were set up before I arrived, but that didn’t matter to corporate. My signature was on the approvals, which meant I was accountable. Wednesday at 300 p.m.
there was a knock on my office door. I looked up and Rebecca was standing there holding her tablet with that focused expression she got when she was deep in analysis mode. Can I come in? I think I found something about the audit. I nodded because at this point I take help from anyone. She closed the door behind her and sat down across from my desk.
I’ve been going through the system logs for the past week. I know I didn’t have to, but I couldn’t stop thinking about it, and I found something you need to see. She pulled up a series of reports on her tablet. There was a vendor payment system error that happened back in August, right before you took over the operations role.
The system was processing payments twice for certain invoices, but only recording them once in the budget reports. So, it looks like there are discrepancies, but it’s actually a software glitch that’s been running for months. I stared at the screen. She was showing me feeling this overwhelming wave of relief mixed with confusion.
You dug through months of system logs to find this. Rebecca, you didn’t have to do that, especially not after everything. She looked at me directly for the first time in 2 weeks. I did it because it was the right thing to do and because I know you care about doing your job correctly, even when we’ve disagreed about methods.
I wasn’t going to let corporate blame you for a system error. I forwarded the information to Patricia immediately and within an hour, corporate was backing off. They confirmed Rebecca’s findings and admitted the audit had been triggered by automated flags that didn’t account for the software glitch. By end of day, they were apologizing for the disruption and promising to fix the payment system.
I went looking for Rebecca to thank her properly and found her in the small break room on the third floor making tea. Hey. She turned around and her expression was guarded. Hey, I walked closer but kept some distance between us. I wanted to say thank you. You saved my job. You saved my whole team. You didn’t have to do that. Especially after I pushed too hard andmade you uncomfortable.
Rebecca set down her mug. You didn’t make me uncomfortable, Connor. I made myself uncomfortable. I got overwhelmed by everyone being in our business, and I panicked. But these past two weeks have been terrible. And I kept thinking about how walking away didn’t make me feel better. It just made me miss you. I felt my heart do something complicated in my chest.
I missed you, too, like a ridiculous amount. And I kept wondering if I should have fought harder to convince you to stay or if giving you space was the right thing to do. Rebecca’s eyes got shiny. I was falling for you. That’s why it scared me so much because if this was just casual, it wouldn’t matter what people thought or if it got messy.
But it wasn’t casual for me and I didn’t know how to handle that. I took a step closer. It wasn’t casual for me either. That’s why these two weeks felt so awful. She looked at me for a long moment. So, what do we do now? Because I don’t want to go back to pretending we’re just boss and employee who barely talk to each other.
That feels worse than taking the risk. I thought about it. What if we stop hiding it? Like actually just be open about dating. file whatever HR paperwork we need to file. Deal with the gossip because it’s going to happen anyway. And if people have a problem with it, that’s their issue to work through, not ours. Rebecca smiled for the first time in 2 weeks and it was her real smile.
I’m tired of being scared of what might go wrong. Let’s just try. We agreed to do it right this time. No more sneaking around. We filed the proper disclosure forms with HR that documented our relationship and confirmed there was no direct reporting structure between us. We told Tyler and Lauren who were both completely insufferable about being right.
Tyler called me three times in one day just to say I told you so in different ways. My parents were thrilled when I brought Rebecca to Sunday dinner the next week. Mom hugged her like she was already family, and dad spent an hour telling embarrassing stories about me as a kid. Rebecca handled it perfectly, laughing at all the right moments and asking questions that made my parents love her even more.
The office gossip lasted about 2 weeks before people moved on to something else. A few people made comments, but most of our colleagues were actually supportive once they realized we were serious. Kevin told me he thought we made sense together, which I appreciated. The power dynamic concerns were real, but Rebecca was careful about documentation and made sure any decisions involving my department went through additional approval channels to avoid conflicts of interest.
We had our first real fight about a month in. I’d made a call about equipment scheduling without consulting her first, and she felt like I’d undermined the process we’d agreed on. We argued in her office after hours, both of us frustrated and talking over each other. But instead of shutting down or walking away, we actually worked through it.
We figured out a compromise where I had more autonomy for day-to-day decisions, but looped her in on anything major. I realized that disagreeing with someone didn’t mean the relationship was falling apart. It just meant we were two different people learning how to be together. 3 months after our disaster first date, I suggested we go back to Giardanos.
Rebecca looked at me like I was crazy, but she agreed when I said I wanted to replace the bad memory with a good one. We sat at the same table, ate, ordered the same food we’d had that first night. Halfway through the meal, Rebecca started laughing. Remember when we first sat down here, and you thought I was going to steal your table? I grinned.
I thought you were the last person on earth I’d ever want to have dinner with. I was so wrong, it’s actually embarrassing. Rebecca reached across the table and took my hand. And now I squeezed her fingers. Now you’re the person I want to have dinner with every single night. We split chocolate lava cake again and I told her about a funny thing that happened at the community center.
She told me about a board meeting where one of the members had accidentally called in from his bathroom. We laughed until our sides hurt and I thought about how natural this felt now compared to that awful first dinner. 6 months in, I took Rebecca back to Jiredanos one more time. I’d been planning this for weeks, coordinating with the restaurant staff, making sure everything was perfect.
We sat at table 8 like always, and we talked and laughed through dinner like we did every time. When dessert arrived, there was a small box on the plate next to the chocolate cake. Rebecca looked at it. then looked at me and her eyes went wide. I got out of my chair and knelt down next to the table.
My heart was pounding so hard I could hear it in my ears. Rebecca, I spent 6 months thinking you were intimidating and out of my league. Then I spent one dinner realizing you were actually funny andkind and nothing like what I’d assumed. And I’ve spent the last 6 months falling completely in love with you. You make me want to be better at everything I do.
You make me laugh. 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 going to be part of my life forever. I opened the box and the ring caught the light. Will you marry me? Rebecca was crying, actually crying, and she nodded so hard I thought she might hurt her neck. Yes.
Yes, of course. Yes. I slipped the ring on her finger and she pulled me up and kissed me right there in the middle of the restaurant while other diners applauded. We sat back down. Both of us grinning like idiots and Rebecca kept looking at her hand. I can’t believe you proposed at the place where we had our disaster first date. I laughed. It felt right.
This is where it all started. Where I realized that sometimes the person you’re trying to avoid is actually exactly who you need. We finished dessert. And as we left the restaurant that night, Rebecca held my hand tight. I thought about how I’d almost missed all of this because I was too intimidated to see past her CEO title.
Sometimes love shows up disguised as the boss who makes you nervous until you take the time to see the incredible person behind the professional mask. And sometimes the worst blind date of your life turns into the best decision you ever
