“You'd be amazing for them,” I say, committing now. “And they'd be lucky to have you. You see things other people miss. You care about the details that matter. You make people feel seen instead of managed. That's rare. They'd be idiots not to want you.”
She opens her mouth, but nothing follows. She's staring at me like I've said something shocking instead of obvious.
“I mean it,” I continue. “You're exceptional at what you do. Not just competent—truly exceptional.”
I sound like I'm giving a performance review. That's not what this is.
“The way you've transformed this gala, the way you think about impact and storytelling and making spaces work for people instead of against them—you make everything better just by being part of it. That's rare.”
Say it. Just say it.
“You're extraordinary, Holly.”
She stares at me, her face going pink. She's terrible at hiding what she's feeling. I can see the surprise, the pleasure, the slight embarrassment at being praised this directly.
I should feel awkward about this. I don't.
But I meant every word.
“Thank you,” she says. “That ... means a lot. Coming from you.”
“Coming from me?”
“You don't say things you don't mean. You question everything, you cut anything that doesn't serve a purpose, and you don't hand out compliments to be nice.” She's looking at me steadily now. “So when you say things like that, I believe you mean them.”
“I do.”
The room feels smaller than it did ten minutes ago. Or maybe we're sitting closer. We're not, but it feels like we are.
* * *
After she leaves, I sit at my desk and replay our meeting.
Holly types the way she talks—in bursts of energy followed by pauses. Click-click-click. Stop. Think. Click-click. She bites her lower lip when she's reading something on her screen. She makes this small chirp of a sound when something works out—not quite a laugh, just a quick, pleased note.
I shouldn't be paying attention to any of this.
I shouldn't be sitting here with that sound stuck in my head.
Another text from my mother dings: Dinner this weekend? Ainsley is free on Saturday.
I let the message sit unanswered.
My mother would find Holly charming if she gave her a chance. She's smart without being intimidating, warm in a way that makes people feel comfortable. She'd navigate that world easily.
And she needs access to people like Evelyn Durst. My mother’s approval would open those doors.
I open my calendar. The holiday dinner with the board is coming up. Then the gala itself just two days later.
Two major events in one week. Two nights of my mother parading eligible women in front of me while my PR team watches for “optics.” Two opportunities to introduce Holly to the exact people she needs to meet.
What if we made a deal? Pretend we are dating, just through the holidays. A few weeks where Holly and I could help each other get what we need.
This is a terrible idea. This is also the best idea I've had in years.
The question is: How do I propose this without sounding like I'm using her? How do I make it clear she can say no—that I'm asking as a friend, not pressuring her as a client?
Assuming we're friends. Are we friends?
