I shot her a warning look, but Dex just laughed—warm and easy, as though my colleague’s question were a playful tease rather than a judgment.
“Guilty,” he said with a grin. “But being the black sheep has its perks. My parents always know how to find me when I’m in trouble.”
Then he shifted his attention back to me. “I’m an artist. But I have to say, that campaign was brilliant. The way you positioned luxury as accessibility? Pure genius.”
The compliment caught me off guard. Most people outside the industry didn’t notice the strategy behind a campaign, let alone appreciate it. But Dex understood. Or at least, he seemed to.
“You’re too kind,” I said, shaking his hand and feeling something like pride flutter in my chest. “I’m Willa. Willa Winslow.”
“The pleasure’s mine, Willa Winslow.” He smiled then—a slow, devastating grin that made Jennifer kick me under the table. “Could I buy you a drink? I have a feeling I’d enjoy getting to know a creative genius like you.”
Jennifer immediately started making excuses about early morning plans and needing to catch the last train home, practically shoving me toward Dex before disappearing with the others. And just like that, I found myself alone with a charming stranger who seemed genuinely interested in my work, my thoughts, my opinions.
We talked for hours that night.
Dex told me about his art, his large-scale paintings that explored themes of isolation and connection in urban environments. He showed me photos on his phone: canvases covered in bold strokes of color that somehow managed to feel both chaotic and peaceful at the same time. His work was beautiful, haunting in a way that made me want to understand the mind that created it.
He’d grown up surrounded by nannies and endless luxury, the kind of life most people would kill for. But all he had everwanted was his parents’ attention. Their love had always come in the form of checks and material gifts. Dex had been expected to step into the family business, a web of high-end political lobbying and corporate influence that he privately called “licking the boots of politicians in designer suits.”
“I’ve been struggling lately,” he admitted as the bar started to empty around us. “The art world is brutal if you don’t have connections. Some days I wonder if I made the right choice, if I should have just joined the family business. But then I think, if I gave up now, I’d be proving them right. And I can’t do that.”
The vulnerability in his voice pulled at something in my chest. Here was someone who understood what it felt like to chase dreams that seemed impossible, to feel perpetually on the outside looking in. Someone who wasn’t afraid to admit that success didn’t come easily.
“Don’t give up,” I said, meaning it. “The world needs people who see things differently, who can show the rest of us beauty we might otherwise miss.”
He looked at me as though I’d said something profound instead of simply being encouraging. “You really believe that?”
“I do.”
“Most people think art is frivolous. Especially commercial marketing people.”
I laughed not because it was funny but because it was true. “Most commercial marketing people forget that what we do is supposed to be creative, too. We’re just selling different dreams.”
That was the moment, I thought later, when he decided I was worth pursuing. Not because I was beautiful or sophisticated or any of the things Kieran’s girlfriends were, but because I understood what it felt like to want something more than the safe, conventional path.
Dex walked me to the subway station that night, and before I descended into the underground tunnels, he asked for my number.
“I want to take you to dinner,” he said. “Somewhere we can continue this conversation without competing with drunk college kids and sports commentary.”
I gave him my number because he was charming and genuinely interested, so different from the buttoned-up corporate types I’d tried to force myself to date. Because he looked at me like I was fascinating instead of merely pleasant company. Because when he smiled, I felt something stir in my chest that had been dormant for months. And yes, I knew he was a nepo baby, the kind of privileged kid who’d never had to work for attention or money, but somehow, that didn’t make him any less magnetic.
Three days later, he took me to a small Italian restaurant in Little Italy, the kind of place with checkered tablecloths and candles dripping wax onto empty wine bottles. He ordered for both of us in what sounded like passable Italian and told the waitress we were celebrating.
“Celebrating what?” I asked.
“Meeting you,” he said simply, and I felt my cheeks warm with pleasure.
Over dinner, he asked about my family, my dreams, my fears. He listened when I told him about losing my parents, about Jude’s decision to enlist, about feeling as though I was drifting through life without an anchor. When I got emotional talking about how much I missed my brother, he reached across the table and covered my hand with his.
“You’re not alone,” he said. “Not anymore.”
It was exactly what I needed to hear. For months, I had felt like I was floating through life without connection—going through the motions of being a successful young professionalwhile feeling hollow inside. Dex offered me something real, something substantial. He offered me a place to belong.
We started dating officially after that dinner. He took me to art galleries and small concerts, introducing me to a world of creativity and passion that had been missing from my corporate existence. He painted a small canvas for me, a swirl of blues and greens that he said reminded him of my eyes when I laughed. I hung it in my bedroom, the first piece of original art I’d ever owned.
I never met his parents, and Dex assured me I didn’t need to. He seemed almost excited by the idea of building a good life on his own terms—of creating something for us that had nothing to do with family expectations or inherited wealth.
For four months, it was perfect.