Page 76 of Trust Fund Baby

“You look like hell,” he said.

“Thanks,” I muttered, twisting the cap off.

I felt like it, honestly. I’d spent the past few months attempting to dive into something that would show my father that I cared—and something that might even help me forget Roxie King. But no matter what I did, nothing stuck. I’d contacted a few of the old companies I’d brought on to Whittaker Holdings in hopes of either joining their ranks or uncovering a new company that I could refer to my father.

But in truth, my heart wasn’t in it. I was quite capable of finding new talent for the family company. I’d been doing it until the time that my father had practically disowned me. But I had no motivation now. I had no one forcing me to do better, no one breathing down my neck. And without that, I had space to realize I didn’t enjoy hunting down the most lavish fashion designers that I knew would be worn by some of the wealthiest people across the world. It might be someone else’s dream job, but to me, it felt surface-level.

We sat in silence for a beat, the hum of lights and thud of treadmills filling the space. My head had been noisy since the night at Whiskey Locker a few months back. Roxie. That kiss. The way she bolted like I’d lit her on fire. I hadn’t talked about her to James since. I knew I had to move on.

“I need to start over,” I said finally, the words landing heavier than I expected.

James turned his head, brows lifting. “Start over how? With work?”

I shook my head. “No. Bigger than that. My entire life.”

His silence stretched, waiting me out. Typical James. He was better at letting things hang than anyone I knew. Finally, I filled the gap.

“I don’t care about Whittaker Holdings,” I said, blunt as a butter knife. “At least not for its intended purpose. Fashion, luxury brands, commodities that only the wealthy would dream of being able to own. Whatever the hell we’re supposed to be selling the world—I don’t care. I’ve been pretending I do, but it’s not me.”

James leaned forward, elbows on his knees. “Then what is?”

I drew a long breath, letting it out slow. I’d thought about this for months, in the quiet moments between parties, women, and the quiet that seemed to perpetuate my mind nowadays. “New York has two problems that hit people harder than anything else: food and housing. You walk ten blocks in Manhattan, and you see it—people living on the street, people who don’t know where their next meal is coming from. It’s survival.”

His eyes narrowed. “So what? You’re going to turn Whittaker Holdings into a soup kitchen?”

I smirked as new excitement filled me. Something I hadn’t felt in quite some time. “Not exactly. But I want to put money and energy into solutions that matter. Building affordable housing. Funding food programs. Real ones, not just some glossy charity gala bullshit that we’re so used to seeing. That’s how I help the most people.”

James studied me as if I’d grown a second head. “And how do you plan on doing that without the backing of your family’s company?”

I swallowed a mouthful of water, the plastic bottle crinkling in my hand. “That’s the thing. I think my father will help me. Or at least allow me to do it. Once he sees that I’m serious and have shown some initiative.”

James barked out a dry laugh. “So, your idea is to show what you can do, then persuade Edward Whittaker to fund you?”

“More or less.”

He shook his head but didn’t look away. “You’ve never gone against him like this before.”

“I know.” My jaw tightened. “But I can’t keep coasting on the path he carved out for me. If I don’t do this now, I never will. And then what? I’ll wake up at forty and still be the asshole playboy everyone whispers about. I don’t think so.”

For once, James didn’t have a quick comeback. He just studied me, like maybe he believed I was capable of something more.

And maybe I did too.

“This is the place,” I told James as we walked up to the building my real estate agent had found for me.

It was old brick, a little worn around the edges, but solid. A wide stoop, cracked sidewalks, paint that had seen better days. Still, something about it made my chest tighten with possibility. I could picture families here, laughter spilling out the windows, kids running up the stairs with food in their bellies.

James gave it a slow once-over. “It’s … not terrible.”

The corner of my mouth tilted upward. “High praise, coming from you. It just needs some elbow grease and love.”

We stood in silence for a moment, the sounds of the street filling in—horns, snippets of conversation, the city always humming. I shoved my hands into my pockets, restless. There was a question sitting on my tongue I didn’t want to ask, but it had been needling me, just like it did every time I was in either his or Hallie’s presence.

“How’s Roxie?” I asked, keeping my tone casual, though the question burned in my throat.

James didn’t answer right away. He shifted, as if he weren’t sure if he should tell me. That hesitation alone nearly gutted me.

Finally, he said, “She’s been dating again.”