Page 18 of The Headmaster’s Rule

Her smile is tight. “No, sir.”

I know this game. I’ve played it with students more times than I can count, and I’ve got all night. I fold my hands, lean back, and wait.

It only takes a few seconds.

“Have you settled on the cause for the fundraiser, then?” she asks.

I grunt, tipping my head toward the ceiling. “Not this again.”

Her brow furrows. “I don’t understand how we’re supposed to promote something when we don’t even know what it’s for.”

I let out a slow breath, removing my glasses to massage the bridge of my nose. I don’t need her pressing me on this.

Especially when I know she’s right.

Goddammit. She is, isn’t she? How can I ask people to volunteer their time, approach donors, plan an entire event, when I don’t even know the cause?

Eleanor reads it on my face before I can speak. “If you could just tell me what it is you’re thinking of… that would at least give us something to work with.”

“I… I don’t know,” I admit after a beat. It’s the first time I’ve said it out loud. She can’t help, but something eases in me having said it. I roll my shoulders, stiff and sore from too many hours hunched over a screen. A dull pulse behind my right eye reminds me I haven’t eaten since breakfast.

She tilts her head, studying me. Her voice is gentle when she says, “Maybe we need to ask what’s best for the students.”

I blink.

Of all the questions I’ve turned over in my mind—donor optics, board politics, parent opinions—not once did I ask that one. And it hits me hard because she’s right. And also… she’s wrong.

Because it’s not that simple. She doesn’t understand that. She can’t.

Eleanor leans in, her voice softer now. “You don’t have to figure it out alone, you know.”

Those words, so kind and earnest, so impossibly compassionate, strike a chord in my chest I can’t afford to acknowledge. Part of me wants to believe her. To trust her.

But that’s a luxury I gave up a long time ago.

She lets out a quiet sigh and leans back, tucking a strand of hair behind one ear. “I’m sorry, sir,” she mumbles. “I didn’t mean to overstep.”

I exhale slowly. “It’s fine.”

“I’ll do whatever you need me to do. Venues, volunteers… give me the list. I’ll handle it.”

I hand over the list of local donors silently. They’ll probably be hesitant after last year, but sending Eleanor is my best bet. Her bubbly charm will win them over.

“Please start by approaching the community partners. Local stores and businesses. Let them know we’re still finalizing the cause and we’ll follow up soon.”

She nods without hesitation, and I pause.

“I’m sure you have a busy social life, but if you could get started this weekend…”

“It’s no problem. I haven’t, uh, made many friends out here yet, so…” Her cheeks flush at the admission, and she laughs lightly. “Anyway, I’ll have time. I was only going to work on lesson planning.”

Something about this doesn’t sit right. She’s young and energetic; she shouldn’t be spending her weekends holed up, working, but it’s not my place to say so.

I rise from the table and, without thinking, extend a hand. Eleanor blinks at it, then stands and shakes it.

“Thank you, Miss Hart.” I try not to notice the warmth of her skin, how soft it feels against mine, or the way my hand easily wraps around hers.

These are not things a boss should notice.