Chapter 29
James
I was falling for Hallie Woods, and I didn’t know what the hell to do about it.
The moment I walked away after our first kiss, I knew. The weekend in the Hamptons only solidified it. But this morning? I woke up with her warm body tangled in the sheets beside me, and there was no denying it anymore. I’d crossed the point of no return.
She was still asleep when I stirred. Peaceful.
Soft. The kind of tranquility I didn’t know I’d been searching for until I found her.
I reached for my phone, trying not to wake her, the glow of the screen casting light across her face.
There was a text from Theo asking to meet for lunch.
Said he had a business proposal and that a quick resolution would benefit us both.
For a minute, I considered ignoring him completely. Turning on Do Not Disturb and spending the rest of the morning exactly where I wanted to be—wrapped around Hallie, with no one else in the world to bother us.
But Theo rarely reached out unless it was important. So, despite every fiber of my being screaming at me to stay, I got up, got dressed, and headed toward the Financial District.
Even on the subway, I was completely calm. I wasn’t checking the pre-market buzz or rehearsing elevator pitches in my head. My focus had shifted. Drastically. And all it took was a certain brunette I’d left alone in my bed—like an idiot—who had turned my whole world upside down.
Later, as I made my way from the Financial District up into Lower Manhattan to meet Theo, my phone rang.
“Mom, hi.”
“You’re still planning on coming to the restaurant tonight?” No greeting. Straight to the point—classic Eloise Rossi.
“Hello to you, too,” I replied sarcastically. I could almost picture the exact eye roll I knew she was giving me right now. “Yes, I’ll be there.”
“Good. Everyone’s going, so it would be pointless if you didn’t make the time.”
She was conveniently forgetting that I was the one who’d suggested we meet for dinner at the restaurant tonight.
I’d thrown it out offhandedly, just looking to sneak in a visit and maybe some of the pizzeria’s famous pasta.
She’d thought it was a fantastic idea and had made a family event out of it, despite my attempts to dissuade her with the reminder that we had already met for family dinner on Wednesday.
Twice in one week felt excessive, even by Rossi standards.
“I’ll be there, Mom.”
“Should we expect Sebastian?”
“Not tonight,” I said, pausing for a second. Part of me wanted to mention Hallie. Part of me didn’t want to open the door to fifty questions I wasn’t ready to answer yet.
“Well, everyone’s getting there at six,” she said, “so be sure to leave the office early enough. I’m sure Berkley Williams won’t collapse if you left before it gets dark outside for once.”
“Yes, ma’am.” I grinned as I said it.
I stifled a laugh at my mother’s groan. There was nothing she hated more in this world than being referred to as ma’am. She said it made her feel like she was one foot in her own grave.
“Don’t ‘ma’am’ me, James Rossi.”
“Listen, I’ve got to go. I have a business lunch to get to. I’ll see you tonight.”
There was a beat of silence before she spoke again, her voice a touch softer.
“I know you’re always chasing the next big thing, and I don’t mean to sound like I’m scolding you. I just hope you’re not burning yourself out, honey. I worry sometimes that you’re so busy building this life of yours, you forget to actually live it.”
“Working hard lets me have the life I want, Mom.”
“I know,” she said gently. “I just hope you take the time to enjoy it, too. To really see the people around you, the ones who care about you. That’s all.”
Her words settled in deeper than I let on.
“I hear you,” I said quietly. “I really do.”
I didn’t know where this line of questioning was coming from, and as I stood outside The Nest, I knew I didn’t have the time to have this conversation. It was far more complicated than a five-minute conversation could unpack. “Let’s talk about this later, Mom.”
The lobby of The Nest was as empty as it was the first time I met Theo here. I half-wondered if they intentionally spaced out guest arrivals for maximum discretion.
“James Rossi, here for Theodore Drake,” I told the concierge.
“Mr. Drake is on the fifth floor, dining at Bluebird,” the concierge replied, presenting a lockbox. I did one last cursory check of my notifications and email inbox before handing over my phone.
“Thank you,” I said, accepting the key card that would grant me access.
Bluebird was one of the many restaurants inside of The Nest and was known for being secluded and quiet.
A hostess led me over to the table and, although it had only been a few months since I last saw Theo, he looked like he’d aged years.
Dark circles stood out against his paler than normal skin.
His face was marked by the same severe frown I’d seen in the handful of interviews he’d given, a frown that seemed like it had been carved into his features by months of stress.
“James, thank you for meeting me.” Theo stood to shake my hand when the hostess announced my arrival.
“Absolutely,” I told him. “I’m happy to make the time.”
“Please, sit.” He gestured to the table. “I took the liberty of ordering a few appetizers. I wasn’t sure how much time you carved out for me, and I didn’t want to take advantage of your busy schedule.”
I kept my expression neutral. Last time we’d met, Theo had passed along information that had made me a king at Berkley Williams. It had also come with strings attached—strings I suspected he was about to start pulling.
“I wrapped everything up at the office this morning,” I told him. “Cleared the afternoon just in case.”
“Smart,” he replied, dividing the appetizers between our plates with meticulous precision. “I’m not sure how much time this conversation will take.”
He had tousled his white-blonde hair, and his usually icy blue eyes looked far more tired than I remembered.
“I believe congratulations are in order,” I said, raising my glass.
He’d just been recognized by Rooster’s board as the proper choice for the company’s next CEO, despite early rumors that the board might look beyond the Drake family for the next person to put at the helm. But in the end, Theo had won them over.
“Thank you,” he said.
“You used my information from our last conversation well,” he added, voice low.
I nodded. Neither of us was willing to dig into that conversation. It had danced too far into a gray area for either of us to risk any illegal discourse.
“Well,” he said after a beat, leaning forward slightly. “No sense in continuing the small talk.”
I was used to Theo appearing aloof and unconcerned about the repercussions of his actions. But the Theo I was lunching with today appeared on edge. His leg bounced under the table and his fingers drummed against the white tablecloth.
Whatever this was, it wasn’t just business. And it definitely wasn’t casual.
“Please.” I gestured in his direction, offering for him to take the lead.
“I’m sure you read the headlines,” Theo began.
“After my brother’s hubris led to his own downfall, I scraped what was left of Rooster back together and am trying to carve something beautiful out of its remains.
I fired every executive that had grown fat and happy under my brother’s leadership.
People that fired others who’d been the backbone of my company for years, just so they could pad their pockets with bigger and bigger bonuses.
I’ve reallocated funds from irrelevant expenditures to benefit employees who have dedicated their lives to Rooster.
But during my close examination of the health of the company, I’ve come across a unique problem that I think you have the skill set to solve. ”
It was impressive—listening to the way Theo had taken a scalpel to his family’s company to cut away the excess fat. But for all his talk, I had no idea why I was sitting across from him.
“What did you find?” I asked cautiously.
“My brother has money set aside to start our own venture capital firm. But that was as far as he got. You, however,” Theo leaned back in his chair, giving me the first glimpse of the business shark that I knew him to be, “you mentioned once that you wanted to start your own firm. Would you consider leading Rooster’s venture capital firm? ”
That may have been the furthest thing I would have expected Theo to call me here for today.
But what was even more surprising was the way excitement pumped through my veins at the idea of having that kind of opportunity. It wasn’t just a job, it was an opportunity to shape something from the ground up. A seat at the table, not just another cog in the machine.
There was only one problem.
Hallie.
The last thing I wanted was to take on a new role that would chain me to my desk to get it off the ground. It would sign our death certificate before we even started.
“I will consider it,” I said slowly.
Theo dipped his head in understanding.
“But,” I added, “I have a few things I would need in order for me to accept the offer.”
“Now you speak my language, Rossi. Please proceed.” Theo grinned, showing nearly all his teeth as he eagerly waited for me to lay out my proposition. “Let’s hear it.”
“Recent developments in my life would require for me to not spend all my hours at the office,” I said. “If I take this on, I want to be able to work flexibly, and I expect the same for my team. I don’t want anyone watching the sunset through a boardroom window five nights a week.”
Theo raised a single eyebrow at my plan.
I charged ahead. “If we’re really going to make Rooster into the kind of company people respect, then this firm has to reflect that.
The financial industry’s never prioritized balance, never cared about its employees’ quality of life.
I think we should be the ones to change that.
Offer the best benefits. Attract the best minds. And still be the best at what we do.”
Theo didn’t respond right away. He just studied me, and for a brief second, I saw something that I could only describe as respect.
“Who is she?” he asked after a beat.
“I’m sorry?” I blinked, caught off guard.
Theo smirked, clearly amused by my confusion. “The girl. The one that’s got you reconsidering your priorities.”
“I’m not sure I know what you’re talking about.” I kept my tone even, careful. Just because I was considering going into business with him didn’t mean I trusted him completely, especially not with something as personal as Hallie.
He waved me off. “Don’t worry. I get it.
If there’s an incredible woman in your life, it makes sense that you’d want more balance.
For what it’s worth, I agree with you. That’s the kind of future I want for Rooster, too.
Not built on greed, not like what my brother turned it into.
My grandfather didn’t build this company to become a cautionary tale about ambition. ”
He leaned forward slightly, his tone softening. “Money warps people. If building something more human matters to you, then you have my full support. I never expected a decision today anyway. Go home. Think about it. Maybe talk it over with your partner.”
Theo glanced at his phone. “Now I’m sorry to cut this short, but it looks like I’m needed back at the office. We will talk soon?”
I stood up with him. “Yeah, we’ll talk soon.”
As I left Bluebird, I found myself turning his words over in my head.
This morning, I’d woken up with every intention of staying in bed and wasting the day away with Hallie. Would I have regretted that choice if I had missed out on this meeting with Theo? Was this even something I wanted to consider?
There were a few things I knew—I loved what I did, and this opportunity would be incredible.
But I also wanted Hallie Woods. I just needed to figure out if there was a world where I could have both.