I watched the clock tick past 3:17 PM, the numbers glowing softly on my computer screen. Most people would see just another afternoon in my office, but I was replaying every moment of the Gilmore Construction meeting in my mind.
My phone buzzed. It was Travis. His text message said. "Hey, this may seem weird and unprofessional. But, how would you like to go to dinner with me on Friday night?" I stared at the text for a full minute, my professional persona warring with something deeper. I shouldn't.
This was a terrible idea. Professional boundaries existed for a reason. I'd helped Travis get his life sorted out, connected him with resources, and now he worked on a project my foundation was funding. Getting involved romantically would be unethical, complicated, and potentially compromise the entire project's integrity.
And yet.
My finger hovered over the phone screen, tracing the outline of Travis's text message. The thought of what if, kept coming into play. What if we can keep our professional relationship and our personal relationship separate. We could make it work. Except we both knew how it would look if someone found out.
I typed and deleted three different responses. The professional answer was easy: "I appreciate the invitation, but I think it's best we keep our relationship strictly professional given our working arrangement."
But my finger kept hesitating over the send button.
The truth was, I hadn't stopped thinking about Travis since that morning in the coffee shop. Not just because he'd needed help—I helped people every day, it was literally my job. But there had been something different about the way he'd listened when I talked, the way he'd trusted me with his problems without even knowing my name. And then watching him in that conference room, seeing how he talked about community engagement with genuine passion instead of corporate buzzwords...
I set the phone down and walked to my office window, looking out at the Portland skyline. In my line of work, I'd learned to read people quickly. I could spot manipulation, desperation, and hidden agendas from across a room. But Travis had been refreshingly transparent—worried about people he cared about, grateful for help, nervous about his new job but determined to do it well.
The smart thing would be to maintain professional distance. I'd built my reputation on being uncompromising, on never letting personal feelings cloud my judgment. The Portland Family Foundation funded millions of dollars in community projects, and I couldn't afford to have my credibility questioned because I was dating a contractor.
But when was the last time I'd done something just because I wanted to? When was the last time someone had looked at me and seen Cali instead of Ms. Reed, CEO of the Portland Family Foundation?
I picked up my phone again and typed: "Dinner sounds nice. But we need to establish some ground rules about keeping work separate. Friday at 7?"
I hit send before I could change my mind.
His response came back almost immediately: "Absolutely. I know a place that's nowhere near any construction sites or foundation offices. Thank you for saying yes."
I stared at the message, a smile tugging at the corner of my mouth despite my better judgment. This was either going to be the best decision I'd made in years, or the most complicated mistake of my professional life.
Probably both.
Why is it taking me so long to pick out a dress? I don't need to impress anyone. He already knows what I look like.
And yet, here I was, struggling between a black cocktail dress and a slim red dress that really shows off my curves. I opted for the red dress. Bold. Unapologetic.
Just like me.
My phone buzzed with a text from Maria Santos, pulling me out of my wardrobe deliberations. "Foundation board meeting, Monday nine AM sharp."
I texted back a quick confirmation.
I grabbed my black heels, put some lip gloss on instead of lipstick and left my long curly hair down. Then, l left out the door. I got into my 2024 Ford Bronco.
The restaurant he chose was this small fine dining Italian spot, twenty minutes from downtown Portland. No one we know will see us.