Chapter 14: The Late Night Connection
Day 42, and I was still at my desk at 9:47 PM.
The merger documents Louis needed were spread across my screen—three companies consolidating, stock structures that required careful analysis to ensure nobody got screwed in the transition.
Complex. Interesting. The kind of puzzle that makes the hours disappear.
My coffee had gone cold an hour ago. I grabbed the mug and headed for the break room.
The office was mostly empty—just the hum of HVAC, the distant sound of a copier running somewhere, the occasional phone ringing in vacant cubicles.
I pushed open the break room door.
Donna looked up from her phone, sitting at the small table near the window.
We both froze for half a second—that awkward moment when you encounter someone unexpectedly and have to decide whether to acknowledge them or pretend you didn't notice.
She broke the silence first.
"The Colombian roast, not the house blend. You have taste."
I looked at the coffee maker, where I'd been about to pour the cheap office coffee.
"You've noticed my coffee preferences?"
Donna's smile was slight and knowing.
"I notice everything. It's literally my job."
She said it without ego, just stating fact, and somehow that made it more impressive.
I grabbed the Colombian roast instead and started brewing.
"Waiting for Harvey?"
"Client dinner running late. He texted twenty minutes ago saying another hour."
"You could go home."
"I could. But then I'd just be sitting in my apartment wondering if something urgent came up that I should handle."
Workaholic recognizing workaholic.
The coffee finished brewing. I poured a cup and was about to leave when Donna spoke again.
"What are you working on?"
I paused at the door.
"Merger documents. Three tech companies consolidating, complicated stock structure."
"And you're still here at almost ten PM because...?"
"Because it's interesting. The way the equity's structured—each company has different share classes with different voting rights, and the merger has to preserve those distinctions while creating a unified corporate entity. It's like a logic puzzle."
Donna's expression shifted—genuine interest replacing polite conversation.
"That sounds complicated."
"It is. But that's what makes it worth doing."
I realized I was explaining without condescension, without the performance of trying to sound impressive. Just... talking about work I actually found engaging.
When's the last time I did that?
Donna gestured to the empty chair across from her.
"Tell me more. I have an hour to kill, and Harvey's client dinners are never as interesting as he thinks they are."
I hesitated.
She's Harvey's secretary. The guy whose golden boy I just beat. This is probably a terrible idea.
But she was looking at me with real curiosity, and the alternative was going back to my desk alone.
I sat.
"Okay. So imagine three companies—Company A has Class A shares with ten votes each, Company B has Class B shares with five votes each, and Company C has Class C shares with one vote each..."
I explained the structure, the conflicts, the solutions. Donna asked intelligent questions—not attorney questions, but smart questions that proved she understood corporate law despite not having a law degree.
She's been Harvey's secretary for years. Absorbing expertise through proximity.
"You could have gone to law school," I said after explaining a particularly technical point about fiduciary duties.
Donna's smile was small and self-aware.
"I could have. Chose not to."
"Why?"
"Because I'm better at making lawyers effective than being one myself. Harvey wins because I make sure he's prepared, organized, and pointed in the right direction. That's more valuable than being another lawyer in a firm full of lawyers."
No defensiveness. Just self-knowledge.
I found that refreshingly honest—someone who'd deliberately chosen their path instead of defaulting into it.
"That's rare. Most people stumble into their careers and pretend it was the plan all along."
"And you?"
Careful.
"I always wanted to be a lawyer. But the specifics—corporate law, financial structuring, this firm—those evolved as I learned what I was actually good at."
Donna tilted her head, studying me.
"You're different when you're not performing."
"Performing?"
"The professional voice. The calculated responses. You do it with everyone—partners, clients, other associates. But right now, talking about stock structures, you're just... enthusiastic. Like you actually care about the work instead of caring about what caring about the work will get you."
She's right. And she noticed.
[BLACKMAIL ARCHIVE: UPDATING DONNA PAULSEN PROFILE]
[TRAIT: OBSERVES BEYOND PROFESSIONAL COMPETENCE]
[TRAIT: VALUES AUTHENTICITY OVER PERFORMANCE]
[NOTE: NOT FOR LEVERAGE - FOR UNDERSTANDING]
I dismissed the notification and realized I'd been about to calculate my next response.
Stop. Just talk to her.
"This is nice," I said honestly.
"What is?"
"Talking to someone without strategizing every word."
Donna's expression softened—something genuine breaking through the professional armor she wore as reflexively as I wore mine.
"That's the first real thing you've said to me. Everything else has been your professional voice."
"Is that bad?"
"It's normal. Everyone has a work voice and a real voice. Most people just don't realize when they're using which one."
Her phone buzzed. She glanced at it.
"Harvey. Deal closed, heading home. I can leave."
She stood, grabbed her coat from the back of the chair.
Conversation over.
But she paused at the door, turned back.
"Scott Roden who prepares for everything—did you prepare for this conversation?"
I thought about lying, deflecting, giving some clever response.
Instead, I told the truth.
"No. That's why I actually enjoyed it."
Donna smiled—genuine, unguarded, the kind of expression I'd only seen in glimpses before.
"Good. Do it again sometime."
She left.
I sat alone in the break room, coffee cooling in my hands, and realized the System was running calculations I hadn't asked for.
[RELATIONSHIP ANALYSIS: DONNA PAULSEN]
[INTEREST DETECTED: NATURE UNCLEAR]
[WIN RATE CALCULATOR ATTEMPTING PROBABILITY ASSESSMENT...]
[ERROR: INSUFFICIENT PARAMETERS]
[QUERY: WHAT CONSTITUTES SUCCESS IN PERSONAL CONNECTION?]
I stared at the notification, then dismissed it.
The System can calculate case outcomes, identify argument weaknesses, archive information. But it can't tell me what to do when someone smiles at me like that.
And maybe that's okay.
I finished my coffee, rinsed the cup, and headed back to my desk.
The merger documents were still waiting, complex and engaging and safe.
But my mind kept returning to the break room conversation.
Donna Paulsen noticed my coffee preferences. Asked intelligent questions about corporate law. Called me out for performing instead of being genuine.
And she wanted to do it again sometime.
The System hummed quietly in the background, trying and failing to quantify something that didn't fit into probability calculations or strategic frameworks.
It's disorienting.
Also... not unpleasant.
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