I glanced at Heidi, who was mid-sentence in what sounded like a pitch for influencer partnerships. The meeting could easily stretch another hour, maybe two if she got on one of her deep-dive tangents about market positioning. The matchmakers, onthe other hand, were the backbone of our entire operation. If they were having problems, that took priority.
“Excuse me,” I said, standing abruptly enough that my chair scraped against the floor. “Emergency with IT. Heidi, send me a recap of the rest of this and we’ll regroup Monday morning.”
She looked annoyed, her perfectly glossed lips pressing into a thin line. But she nodded.
We’d carved out a separate space for our matchmakers. It was usually a calm environment with the kind of Zen atmosphere we’d deliberately created to help them do their best work, with soft lighting, plants in every corner, ergonomic chairs that cost more than my first car.
Today, it looked like a war zone.
Matchmakers were clustered in tight groups near the coffee station and around desks, talking in heated whispers. A few had their arms crossed, defensive body language that set off alarm bells in my head. The IT team was huddled around several computers on the far side of the room, looking cornered and defensive.
This was bad.
Henry spotted me the moment I cleared the doorway and waved me over with an expression that clearly saidthank God you’re here.
“What’s going on?” I asked, keeping my voice low.
“The update.” He ran a hand through his already disheveled hair, making it stand up at odd angles. The man looked stressed in a way I hadn’t seen since our last major server migration. “The matchmakers hate it. They’re saying it’s going to make their jobs harder, not easier, and they’re already drowning in applications as it is.”
“Shit. Show me.”
He pulled up the new interface on his screen, and I could immediately see the problem. The update we’d spent threemonths designing and testing was supposed to handle our increased volume.
But it had also changed the priority weighting to favor industry matching over the holistic approach our matchmakers preferred. What looked like elegant efficiency on a flowchart apparently felt like handcuffs to the people who actually did the work.
Our matchmakers took their jobs seriously. It was what made us so damn good at what we did. They went through every single profile and read every line, every carefully crafted answer to our compatibility questions. They didn’t completely trust computers and algorithms to make the best match, even though the algorithms were objectively very good.
They trusted their instincts. Their experience. Their ability to see something between two people that a dataset might miss.
“It’s too rigid,” a matchmaker named Jessica said, appearing at my elbow like she’d been waiting for her moment. She was one of our senior matchmakers, had been with us since year two. If anyone’s opinion mattered, it was hers. “The old system let us see the whole person. We could evaluate their hobbies, their values, their quirks. All the things that make someone who they are. This new system is basically saying ‘you’re both lawyers, you should date.’ But that’s not how people work.”
“The algorithm is very good,” I argued, immediately defensive. I’d personally overseen its development. “The success rate data?—”
“The algorithm is wrong,” she cut me off. “Look, I know you built this company on data and metrics. That’s your wheelhouse, and I respect that. But the reason Cupid’s Arrow works better than all those other dating apps is because we have humans in the loop. We catch things the algorithm misses. We see connections that don’t make sense on paper but work beautifully in reality.”
“She’s right,” another matchmaker added, a younger guy named Caleb. “This update is going to turn us into glorified data processors. And honestly? If that’s what you want, you don’t need us. Just let the algorithm do everything and save yourself the salary expenses.”
The update would make the process faster, that much was true. More streamlined. Better for handling the volume that was only going to keep increasing as we scaled. We’d be able to process twice as many applications with the same number of people.
It was also, I had to admit, completely soulless.
The magic of Cupid’s Arrow had always been the human element. That personal touch was what people paid premium prices for.
“Plus, this system is going to start matching people within the same industries without any safeguards,” Jessica continued, clearly on a roll now. “Same companies, even. We’re going to have bosses matched with their employees, colleagues matched with each other, coworkers who see each other every single day suddenly being told they’re soulmates. It’s a recipe for disaster.”
Someone in the back of the room laughed. “Yeah, can you imagine? The CEO ends up matched with his assistant or the lady who cleans his office. Talk about awkward.”
My stomach dropped. The pleasant buzz from earlier evaporated completely, replaced by something cold and uncomfortable that settled in my chest.
I’d been spending time with Ina like this entire situation was fine. Like the power dynamic between us didn’t matter. Like it was just some technicality we could laugh about over wine. I’d been ignoring the fact that I signed her paychecks and controlled her professional future like it was just a minor detail we could work around.
Denial could be a powerful thing.
If our relationship ended badly, she would be the one who suffered professionally. She would be the one with whispers following her around the office. She had mentioned being worried about being labeled a hoebag, and I’d tried to be comforting, but it wasn’t an irrational fear. Any future employers would question her judgment if this got out. Her reputation would be forever marked by the fact that she’d slept with her boss.
“Dane?”
Henry’s voice pulled me back to the present, yanking me out of the spiral of guilt and self-recrimination. “Sorry. What?”
