My Boss Overheard Me Tell My Best Friend I Couldn’t Stop Thinking About His Smile

Sarah Jenkins

I had three inviolable rules.

Never mix business with pleasure. Never trust a charming man. And never, under any circumstances, get involved with Damon Cross.

Damon was my boss – owner of the Obsidian, the most exclusive club in the city, and head of a criminal empire inherited from his father. He was also the most arrogant, infuriating, and irresistible man I had ever met.

He had been pursuing me for three years. I had always refused him.

That changed on a quiet Thursday afternoon when he overheard a conversation never meant for his ears.

The Obsidian’s offices were unusually still, so I used the lull to call Ivy – my best friend, and the only person who truly understood why I’d spent three years keeping Damon at arm’s length.

“I already said no,” I whispered, glancing at the office door to make sure no one was nearby.

“But why?” Ivy asked. We’d had this argument more times than I could count. “He’s gorgeous, rich, powerful, and completely obsessed with you.”

“He’s also my boss, arrogant, and a player.” I straightened the papers on my desk, trying to redirect my attention anywhere except the frustration tightening in my chest. “You know why this can never happen.”

A pause. Then: “But you like him. Admit it. You can’t go five minutes without saying his name.”

I set my pen down harder than I intended.

“Maybe I find him attractive,” I said. Heat crept up my neck the moment the words left my mouth. “That doesn’t mean anything. It would still be the worst idea of my life.”

“Attractive?” Ivy nearly shouted. “Riley, you’ve been in love with him for – “

“I am not in love with him.”

The interruption came too fast, too sharp to sound convincing even to me. I stood and started pacing.

“He’s fine,” I continued, filling the silence. “Gorgeous, infuriatingly irresistible, and even funny when he isn’t being an arrogant idiot. And he has that smile – “

“That smile that what?”

The voice behind me was low, unhurried, and unmistakably his.

I turned slowly.

Damon stood in the doorway with his arms crossed, a dangerous smile curving his lips. His dark eyes made it perfectly clear he had heard every word.

“Ivy, I’ll call you back.”

I ended the call before she could make things worse.

He pushed away from the doorframe and walked toward me with that controlled, deliberate confidence that always managed to unsettle me. Each step seemed to echo in the silence. I gripped the edge of the desk.

“No, please – continue,” he said. “You were talking about my smile.”

“I wasn’t talking about you.”

The denial was too weak to be worth anything.

His eyes narrowed with amusement. “Who else do you know who’s gorgeous, funny, and has that smile?”

“Lots of people.”

Even I could hear how ridiculous it sounded.

He closed the remaining distance and placed both hands flat on the desk, one on either side of me. He didn’t touch me – but I was trapped between him and the hard wooden edge.

“Liar.”

The word was quiet. Certain.

“Damon. Move.”

“Not until you say it again.”

He leaned closer. I felt the warmth of his breath against my face.

“I’m not going to – “

“Say it.”

I looked at the face that had kept me awake more nights than I would ever admit.

“You’re too arrogant,” I said at last.

His smile widened slowly. “But irresistible. You admitted that.”

“I admitted nothing.”

“You said I was gorgeous.”

“I said someone was gorgeous.”

“And funny.”

“You’re not funny. You’re irritating.”

His laugh was low and warm. “And yet you think about my smile.”

I found enough resolve to push him back and slipped quickly around the desk.

“This is workplace harassment.”

He leaned against the desk, completely at ease.

“It’s mutual flirting. There’s a difference.”

“It is not mutual.”

“Your red cheeks disagree.”

I touched my face before I could stop myself.

“I’m hot.”

“So am I,” he said, the amusement fading into something quieter and more serious. “Since the day you walked into my life.”

For one dangerous moment, I wanted to believe him.

Then I remembered exactly why I couldn’t.

At the door, I turned back.

“Damon. Stop this.”

The playfulness left his face entirely.

“Why? Give me one real reason.”

The directness of it caught me off guard.

“Because if I give in, I lose control of everything.”

Something shifted in his expression – not quite understanding, but close. He took a step toward me, then stopped when I pulled back.

“What if I promised you wouldn’t lose anything?”

“You can’t promise that.”

I left before he could answer. Before I did something worse than admitting the truth.

Three years earlier, everything had been different.

I had been a nervous woman desperate for stability, and Damon Cross had been the intimidating employer I was about to meet for the first time.

I still remembered my first morning at the Obsidian with uncomfortable clarity. I had arrived too early, my hands damp around the folder holding my résumé – even though I’d already been hired. In daylight, the club was stripped of its mystery and glamour. It was simply a building. A building where I needed a job badly enough to ignore the rumors about its owner.

I had been adjusting my blouse for the third time when a deep voice came from directly behind me.

“You’re the new secretary.”

Damon had been thirty-two then, already in complete command of the empire he’d inherited. His suit was immaculate, his posture assured, and his dark eyes looked like they could see straight through every defense I’d ever built.

“Yes. Riley Bennett.”

“Damon Cross.” He extended his hand. “Welcome.”

The moment our fingers touched, something unwelcome traveled the length of my arm.

“You’re different from the others,” he said, studying me with open interest.

I withdrew my hand.

“Thank you.” I held his gaze. “Where is my desk?”

What He Meant by “Different”

He showed me himself. That should have been my first warning.

The Obsidian’s back offices were nothing like the front of house – no black marble, no low lighting designed to make everyone look expensive. Back here it was fluorescent bulbs and filing cabinets and a printer that, as I would discover by noon, jammed every forty minutes without apology. Damon walked me through the space with his hands in his pockets, pointing out the supply room, the break room, the door I was never to open without knocking twice first.

“That’s your desk,” he said, stopping at a workstation near the window.

It was a good desk. Wide, solid, already stocked with everything I’d need. Someone had put a small succulent in the corner. It looked like it had been there a while.

“The last assistant’s?” I asked.

“Three assistants ago.” He said it without embarrassment. “They kept leaving.”

“Why?”

He looked at me with something I couldn’t read yet. “They found the work too demanding.”

I sat down, pulled the keyboard toward me, and started cataloguing what was already on the desktop.

“I don’t find things too demanding,” I said.

That was the moment, I think. Not the handshake. That sentence. Because he went quiet in a way he hadn’t been quiet before, and when I looked up he was watching me with an expression that had nothing professional in it.

“Good,” he said. Then he walked back to his office and closed the door.

I didn’t see him again until four in the afternoon, when he came out with a stack of folders and dropped them on my desk without a word. I worked through them until seven-thirty. When I finally gathered my coat and bag, his office light was still on.

I knocked once.

“I’m done for the day.”

A pause. “You stayed.”

“You gave me work. Was I not supposed to finish it?”

Another pause, longer. “Most people leave at five.”

“Most people don’t need this job as badly as I do.” I regretted it immediately – too much, too honest for a first day. I pulled my bag strap up. “Goodnight, Mr. Cross.”

“Damon.”

“Goodnight, Damon.”

I didn’t look back. But I heard his chair push back from his desk, and I walked faster.

The Part I Never Told Ivy

The reason I couldn’t give in had nothing to do with rules. Not really.

My mother had loved a powerful man once. Completely, stupidly, with everything she had. He’d been charming and certain and so sure of himself it felt like standing next to a wall – solid, immovable, safe. Until the day she needed that wall and it wasn’t there. Until the day his certainty turned out to be about himself, not about her. Until the day she came home to an empty apartment and a note that said he’d found someone less complicated.

She never really recovered. Not all the way.

I was seventeen when that happened. I watched her rebuild herself from the outside in – new job, new apartment, new routines – while something behind her eyes stayed permanently dim. She smiled at the right times. She asked about my school. She was fine.

She was not fine.

I swore, standing in the kitchen of that smaller apartment while she made us dinner and hummed like nothing had changed, that I would never hand anyone that kind of power over me. Not ever. Not for anything.

So when I walked into the Obsidian at twenty-six, broke and desperate and already feeling something inconvenient at the brush of Damon Cross’s hand, I knew exactly what I was doing when I pulled back.

I was protecting the thing my mother lost.

The problem was that Damon didn’t behave the way powerful men were supposed to. He didn’t lose interest when I said no. He didn’t pout, or turn cold, or find someone else to focus his attention on. He just kept showing up. Asking questions about my weekend. Leaving coffee on my desk before I arrived. Remembering, somehow, that I hated cilantro and making sure it never appeared in the lunch orders.

Small things. Consistent things.

The kind of things that are much harder to defend against than grand gestures.

The Thursday Everything Cracked

I’d been running on four hours of sleep when I came in that morning.

My upstairs neighbor, Gary, had decided eleven-thirty PM was an excellent time to rearrange his furniture. I’d lain in bed listening to something heavy scrape across hardwood for forty minutes before giving up entirely and making tea and sitting at my kitchen table until three AM, reading a book I couldn’t concentrate on.

So when Damon came out of his office at nine and said he needed the Hartley contracts pulled and reorganized before the two o’clock meeting, I said “of course” and meant it and then spent the next hour reading the same paragraph on page four over and over without absorbing a single word.

By eleven I had a headache behind my left eye that I was choosing to ignore.

By noon it was not a headache anymore. It was something else. Something that started in my chest – not pain exactly, more like pressure, like the air was slightly thicker than it should have been.

I went to the break room and drank a glass of water. Then another. Stood at the sink and looked out the small window at the alley below and told myself I was tired, just tired, and that the contracts would get done and the meeting would happen and I’d go home at a reasonable hour and sleep.

I was halfway back to my desk when my legs made a different decision.

I didn’t fall dramatically. Nothing like that. I just sat down on the floor in the corridor outside the break room, quite suddenly, because my legs had stopped consulting me. The wall was right there and I put my back against it and thought, with strange calm, that I should probably tell someone.

I didn’t get the chance.

What He Did Next

I don’t know how long I was there before I heard his footsteps.

They stopped.

“Riley.”

Not a question. Just my name, in a voice I’d never heard from him before. Lower than usual. Stripped of everything except the two syllables.

Then he was on the floor next to me, one hand on my face, tilting my chin up. His palm was warm. I noticed that stupidly, specifically – warm and dry and very steady.

“Look at me.”

I looked at him.

“What happened?”

“I sat down,” I said. It sounded ridiculous.

“You’re white.” His other hand found my wrist, fingers pressing against my pulse. “How long have you felt like this?”

“Couple of hours. It’s nothing. I didn’t sleep.”

“It’s not nothing.” He stood, and before I could say anything about being perfectly capable of standing on my own, he picked me up. Completely. One arm under my knees, one at my back, like I weighed nothing worth mentioning.

“Damon – “

“Don’t.” His jaw was set. He was already moving.

He took me to his office – not the break room, not the lobby, his office – and put me on the leather sofa against the wall. Then he pulled his phone out and made a call and said four words I caught through the fog: “Get Marcus up here.”

Marcus turned out to be a man built like a refrigerator who arrived in under three minutes and who, I would later understand, had a medical degree he’d stopped using when Damon’s father offered him a different kind of work. He checked my blood pressure, asked me questions, shone a light in my eyes, and then told Damon something quietly that I wasn’t meant to hear.

Damon’s expression didn’t change. That was the thing. Most people, when they’re worried, let it show somewhere – the eyes, the hands, a tightening around the mouth. Damon just went very still. Like a room before a storm decides what it’s going to do.

“You’re going to rest,” he told me, when Marcus left.

“I have the Hartley contracts.”

“I have other people.”

“You hate how other people do the contracts.”

Something moved across his face. “Riley.”

“I’m fine.”

“You passed out in my hallway.”

“I sat down.”

“Same thing.” He pulled his jacket off and folded it and put it over me before I could object, and then sat in the chair across from me and looked at me with an expression I’d spent three years telling myself I was misreading.

I wasn’t misreading it.

“Why do you always do that?” I asked.

“Do what?”

“Act like I matter.”

The question came out wrong – too raw, too direct. The kind of thing you say when you’re tired enough that the filters stop working. I looked at the ceiling.

He was quiet for a long moment.

“Because you do,” he said. “That’s not an act.”

I kept looking at the ceiling. My chest did something I couldn’t name and didn’t try to.

“The contracts,” I said.

“Will get done.”

“If they’re wrong – “

“Then it’s my fault for not letting you do them.” He leaned forward, elbows on his knees. “Riley. Stop.”

So I stopped.

I lay on his sofa under his jacket while the afternoon moved past the window and he sat in the chair across from me and worked on his laptop, not talking, not pushing, just there. Present in that still, certain way of his that I had spent three years pretending not to need.

I fell asleep at some point. When I woke up the room was dimmer, late afternoon light going orange at the edges, and Damon was still in the chair. He’d put the laptop away. He was just watching me.

“How long was I asleep?”

“Two hours.”

“You stayed.”

He looked at me steadily. “You stayed late on your first day because I gave you work. Did you think I wouldn’t stay?”

I sat up slowly. His jacket slid off my shoulder and I caught it and held it in my lap.

“The meeting,” I said.

“Handled.”

I looked at the jacket in my hands. Gray wool, expensive, smelled like whatever he wore that I’d spent three years pretending not to notice.

“Damon.”

“Yeah.”

“I’m still not going to – ” I stopped. Started again. “This doesn’t change the rules.”

He nodded slowly. “I know.”

“I mean it.”

“I know you mean it.” He stood, took his jacket gently from my hands. “But you told Ivy I was irresistible. So I figure I’ve got time.”

I laughed before I could stop myself. Actually laughed, short and reluctant, and he smiled at it – that specific smile, the one I’d been describing to Ivy when he walked in – and for a second the whole architecture of my refusal felt less solid than it had that morning.

“Go home,” he said. “Sleep. Eat something.”

“You sound like someone’s father.”

“I sound like someone who watched you pass out in his hallway.”

“I sat down.”

“Goodnight, Riley.”

I got my bag. At the door I stopped, and I didn’t turn around, because turning around felt like a line I wasn’t ready to cross.

“Thank you,” I said. “For the jacket. And the – ” I didn’t finish. “Thank you.”

“Anytime,” he said.

And the thing was, I believed him.

That was the part that scared me most of all.

If this one got under your skin, send it to someone who’s been making excuses not to admit something.

For more thrilling tales of unexpected connections and high-stakes drama, don’t miss “My Employer Told the Staff I Was “Just the Maid” – She Said It Right in Front of His Father”, “I Spilled My Drink on a Stranger in a Hotel Lobby – Then He Said “They Followed Me Here””, and “My Boss Was About to Get in That Car – I Had Four Seconds to Decide”.