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English
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Published:
2026-05-11
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1,206
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1/1
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how do i ask your dad out?

Summary:

You ask Sherry for advice on how to ask out her dad, and walk away with unexpected results.

Leon Kennedy/Reader

Notes:

something fun i came up with; can also be read on tumblr at twentytomidnight :)

(See the end of the work for more notes.)

Work Text:

It's easy to find Sherry—she's always behind her motherboard of screens, her sanctum sanctorum. Locked into a system that rarely sleeps, rarely provides her rest.

What's of utmost importance is finding her at a time when she's accessible. When those headphones are tucked around the thin width of her elegant neck, indicating that she is at rest. This is why you must find ideal time to speak with her, something both rare and difficult to achieve.

But it seems like the cards are in your favor today. When you slink by her office, making cursory check—the lights are dimmed, the headset is slung around her neck—she assumes relaxed posture at her desk.

The pulse of your heart is rapid-fire but you can't turn away from the threshold now. Not when it has been offered so nicely to you.

You knock gently on the door frame to avoid startling—she turns at the sound and you make visual contact with cornflower blue eyes that crinkle in familiarity at your approach. Awaiting your introduction for reasons yet unknown—time to proceed.

"Can I ask you for advice, Sherry?" You ask with a careful, genial smile as she completes rotation in her seat to you.

She nods, and her smile becomes more indulgent, eager to be audience to a friend's request. "Yeah, what's up?"

You dawdle in the doorway before you cross the point of no return, working your hand around the span of your other wrist. It takes the hesitation of a second to stare at the floor before you look back up to her.

"Well, it's a little awkward—"—You begin delicately, and force the words before you lose nerve—"—But I'd like to ask Leon out."

At this, her face draws most still, quite neutral—with the impartiality of judge, jury and executioner. You suppose that it is quite a nuclear missile that you've dropped into her lap.

"Oh. Really?" She asks, and you could swear that you see the trace of a smile at the corner of her mouth—further adding to the excruciating twisting in the wind you must endure.

"Yeah." You reply bracingly, and when she offers nothing more; you realize she's awaiting explanation. Well, considering this is something you've sacrificed yourself to at the altar of her assistance, very well.

"I mean—he's Leon." You declare, as though this is substantiative enough to reply with.

"I've been meaning to for a while now, but I just never had the chance to get around to it—"—She tilts her head at this submission of information—"—And I think now is better than ever."

Sherry tilts her head, watching you with deliberate analysis, her eyes taking watchful ken. "How long have you been meaning to ask him?"

"Um—"—You realize that this will perhaps make you seem quite silly when you answer this inquiry—"—Ever since that mission in Joburg."

Joburg has been quite a while since now. Judging from the way that Sherry's brow continues to jump up the length of her forehead—it's quite long by her reckoning as well.

"Don't judge me." You cast out into the darkness, wishing for a divine bolt of intervention to obliterate you now.

"I'm not—"—Sherry levies out a hand to ease your dander—"—But what are you asking me for?"

You flounder in the midst of the many different answers that are pinwheeling in your head. The most suitable one that you settle upon is this: "Well—he's Leon."

Sherry remains stolidly silent and it prompts you to provide further elaboration. Your hands flail as you try to find something better to supplement your initial response.

"I want to ask him out somewhere nice. Somewhere that'll spoil him."

At this, the dam finally breaks. Something affectionate and slow takes marked appearance in the smile that she displays for you.

"You want to spoil Leon?" She asks, as though the concept is a little goofy—which, you suppose it is.

"Well—why not?" You ask, and there's the heat of self-defense made present as you assert your rebuttal.

"He's funny, he's smart—he's—uh—"—You're reminded you're talking to Leon's daughter in all-but-name—"—Pretty nice on the eyes."

This summons a laugh from her, a chirrup of noise at your diplomatic wording.

"Pretty nice on the eyes?" She repeats you in blatant amusement.

You keep an element of abashed self-deprecation in your voice. "Sherry, I'm not about to call your father figure hot to your face."

"Well, why don't you say it to mine?" You hear—and were it not for the fact that it was clearly articulated through a heady sheen of static, the ghost from the machine—you would consider passing away.

But all that you can do is remained fixated to the spot, transfixed upon the phone that sits guiltily beside Sherry's arm. A phone that is markedly alighting with the Caller ID of a face that brings forth delight. But not in this moment.

Mentally, you careen—outwardly, you're certain that you look no better, as you find your eyes darting wildly from the damning phone to Sherry, who sits. It's clear she holds some modicum of remorse for being the accessory to the crime. But not by much.

"Oh my God—"—You're grateful for the stability your voice retains, thought you're uncertain how long this will last—"—Leon? Have you—"

The voice that is unmistakably Leon's speaks through the phone that is on speaker—your curse yourself for not making more definitive inventory of the room as you made your way in.

"You know, in my old age," Leon comments with a degree of good humor, "I don't get as many compliments as I used to."

He pauses for a moment, letting you further wallow in your self-inflicted torment—unable to tear your eyes from the phone.

"Nice to hear I still got it." He tacks on. You know Mr. Kennedy well enough to know that he's got a broad smile on his face, wherever he is in the world.

"Uh—I'm—"—You find yourself quite articulate in this moment of distress—"—Um."

"And—"—Leon continues, saying your name to bring you to attention—"—If you're free Sunday at seven—"

You realize like Sherry, he is awaiting your response. Like daughter, like father. "Yeah?"

Leon sounds pleased, something that makes your heart race and spur to life within—"—I like Italian food."

With the gravity of his assertion placed into the careful atmosphere suddenly cultivated in the room, he makes his farewell. "See you both later."

You're barely aware of Sherry's goodbye, nor your own, before the call ends—and then you and Sherry are left together in a new battleground.

"I'm going to pass away." is the first thing that you say when you've finally gathered your wits—and taken care to ensure Sherry is aware of her culpability in the circumstances.

Finally, cat out of the bag, she regales you with a genuine smile. "Not if you want to go on that date with him, you won't."

And you find to your disdain and desire—that she's correct. After all, you have a commitment with Mr. Kennedy that you're finding you're most looking forward to.

Notes:

thanks for stopping by! hope you enjoyed :)