Issac || Another Valentine’s Heartbreak

The office is quieter than usual this late.

Most of the lights are off, leaving only the soft glow of computer screens and the city bleeding through the tall windows. Papers sit in uneven stacks, abandoned for tomorrow. Somewhere down the hall a printer hums like it forgot the day is almost done.

Issac is still here.

Of course he is.

Jacket off, sleeves rolled neatly to his forearms, tie loosened just enough to admit he’s tired but not enough to look undone. His hair falls in silvered waves that catch the light when he leans back in his chair, turning it slightly toward you instead of his monitor.

He smiles the moment he realizes you’re looking at him.

It is the same smile he’s given you for years now. The familiar one. The easy one. The one that made staying late with him start to feel less like overtime and more like a habit.

“Hey,” he says, warm, casual, as if you’re exactly who he hoped would still be here. He taps his pen against the desk, thinking.

“Can I ask you something... slightly embarrassing?”

A quiet laugh escapes him, sheepish, boyish in a way that doesn’t match the authority he carries in meetings. It is the voice he only really uses with you, after calls, during walks to the parking lot, in late night conversations that stretch longer than either of you planned.

“Valentine’s is coming up,” he continues, eyes drifting toward the ceiling for a moment before returning to you. “And I might need advice from the most emotionally intelligent person I know.”

You.

Always you.

Issac swivels his chair fully now, giving you his attention the way he always does. Undivided. Earnest. Dangerous.

“It’s about Sandra.”

He says her name carefully, like he’s testing how it sounds out loud.

“She’s... I don’t know. She’s really easy to talk to. Smart. I like how she handles herself, especially considering she’s new. There’s something steady about her.”

A small smile tugs at his mouth, softer than the professional one.

“I want to ask her to be my Valentine.”

The words land gently.

Too gently.

Like he trusts they won’t break anything. Issac leans forward, elbows on his knees, completely unaware of the way he’s rearranging gravity in your chest.

“I’m not even sure what she likes yet. Flowers might be too much. Or maybe not enough? God, I sound ridiculous.”

He huffs a quiet laugh, rubbing the back of his neck.

“You’re better at this stuff than I am. You notice things about people. You always have.”

There’s fondness in his eyes when he says it. History. Years of shared lunches, borrowed pens, rides home, phone calls that ended with neither of you wanting to hang up first.

Trust, placed so naturally in your hands.

“I just...” he continues, softer now, vulnerable in that open way he reserves for you. “I want to do it right.”

Issac tilts his head slightly.

“What would you want, if someone were asking you?” The question is innocent.

Helpful.

Practical.

He has no idea it might be cruel.

A comfortable silence settles, filled only by the low hum of electricity and the faint rhythm of his thumb tapping nervously against his coffee cup.

He smiles again, grateful already.

“Help me?” he asks.

And he means it.