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baby daisy, can i request dean smith crushing on his secretary ( aka the reader ) i'm bored at my office job!! (headcanons or drabble, whatever you're in the mood for~) ily 🩷🐸 - @wendichester

𝒇𝒊𝒓𝒔𝒕 𝒑𝒐𝒊𝒏𝒕 𝒐𝒇 𝒄𝒐𝒏𝒕𝒂𝒄𝒕,

pairing — dean smith x secretary!reader

word count — five hundred & eighty seven

warnings — none, really. just corporate dean having a crush & very cute office dynamics and banter!

notes — thank you for the request, liv!! turns out that i was in the mood for both 😌 the drabble is just a sweet little intro to this dynamic. i've never made headcanons for characters that weren't ocs so this was SCARY lol but i hope you like them!!

introductions were brief when you’d first met, pleasantries even briefer, and dean was quick to pick up on the fact that you weren’t one to waste words. every sentence that left your mouth had its purpose. each one tinged with a layer of wit, and efficiency. the small, knowing smirk that you seemed to always be sporting? could have easily been misconstrued as cocky or smug, but dean saw and appreciated it for what it was—beautiful, yes—but also confident and playful, as reflection of who you were.

you were the first point of contact. not only the face of the office, but the backbone of it. the one truly running the show. another thing dean had been quick to pick up on. he’d seen it on his first day at sandover, when you’d walked him through the office, giving him the rundown of the place. you may have been confined to the twenty-second floor, but it was clear that you knew the whole company inside and out. you knew what your brought to the table, knew that you were single handedly keeping the department from falling apart. dean figured it’d be heaven to be on your good side, and hell if anyone was ever foolish enough to do anything to get on your bad.

you knew everyone by name—employees and clients alike, memorized each and every extension, relayed every important message, handled correspondence, managed every schedule change, kept up with every document, record, meeting and appointment…yet, you still had a way of making dean feel seen—special, in a way that made coming into work the best part of his day.

you’d made him comfortable the minute he stepped foot into the building, and from day one, you had let him know that you'd always have his back now that he was apart of the team.

“are you nervous?” you'd asked, hand straightening his tie on instinct after you had finished showing him around. your touch–not invasive, just helpful.

“no, not at all.” dean had said, but you could see the cracks in his facade, and you met his gaze, keeping your eyes on him until he revealed the truth—until he understood that it wouldn’t help to lie to you, or himself. “okay, maybe a little.” he confessed, his mouth quirking up on one side.

“don’t be.” you told him, voice stern, eyes demanding. you weren't being blunt. you were holding him to the standard, warning him not to doubt his own capabilities.

“the other sharks will eat you alive if they feel like you can’t handle the stakes, and you wouldn’t have gotten the job if that were the case, right?”

“right.”

“right.” a beautiful smile graced your face again, your point haven been made. “so, take care of business—with confidence, and you'll be fine.” you told him, sure of your words. genuine care behind your advice.

“is there anything else that i can help you with, mr. smith?”

“no–no. you've been great, thanks. more than i could have asked for, really.”

“it's my job.” there was an unspoken, and i do it well, written in the relaxed smile on your face, and although dean had only been in your presence for half an hour, he knew that it was true.

“–and one more thing.” you said, turning in the doorway, hand on the frame.

“yeah?”

“welcome to the team.” you’d said it so gently, so genuinely soft and welcoming that looking back, dean thinks it was the very moment that he began to fall for you.

𝒉𝒆𝒂𝒅𝒄𝒂𝒏𝒐𝒏𝒔,

🐸 if he’s not in a meeting, he keeps his door open for most of the day if only to catch the sound of your laughter drifting down the hall. hearing it always brings a smile to his face.

🐸he notices every time you change anything, and always compliments you on it.

🐸 if you're ever out sick, he actually pouts about it. chest deflating when he notices that someone else is filling in for you. all confident and playful banter the moment you return:

"this place nearly fall apart without me?" you ask.

"i know i did." he admits, a deep blush spreading across his cheekbones when he realizes what he just said out loud.

🐸 if anyone ever has anything negative or inappropriate to say about you, he takes up for you without even thinking about it.

🐸 sometimes you come in to find flowers on your desk, no card, no note, but you’ve got an idea about who they’re from. & afterwards, when you seem him:

“good morning, mr. smith.”

“good morning.” he says, feigning innocence.

“you wouldn't happen to know where these came from, would you?”

“no idea.”

🐸 dean very quickly finds himself valuing your opinion. it starts at home. in the morning when he’s getting dressed for work. he becomes hyper aware of how he combs his hair, the suits he decides to wear, what tie he thinks you’ll like. you compliment him ONCE on a deep, cherry red one, and now he subconsciously reaches for it more often than the others.

🐸 he swears he doesn’t do it on purpose, but sometimes he’ll come in with his tie askew, or one of the cuffs of his sleeve unbuttoned, knowing that you’ll stop him in his tracks as he passes your desk—your eyes narrowed with a playful, accusatory look as you get up to fix it for him, reminding him that “presentation is everything, smith.”

🐸 at first, he didn’t like the fact that you refused to call him dean. especially since you addressed nearly everyone else in the office by their first names (he was definitely jealous) calling someone by their first name in a professional environment is big. it’s relaxed, casual, somewhat intimate, playful even, but for you, it was also earned. the people in the office who you still address formally? they’re either new or on your bad side.

🐸 the progression goes like this: mr. smith, smith, dean. the first time you call him ‘dean’, he’s at the office late—stressing over numbers he can’t quite get right. you pass his door, then backtrack, leaning in. he’s nose deep in spreadsheets, and doesn’t notice you at first, but the second the soft, “dean, are you okay?” leaves your mouth, his attention’s yours. he looks up, momentarily forgetting why he was even stressed. he just stares at you for at least twenty seconds, then he smiles. "perfect." he tells you, and you nod before making him promise that he won't stay too much longer.

🐸 whenever he starts to talk about his weight, you wave him off, reminding him that he looks great. "besides, there's more to love." you argue, a long stretch of silence follows. "at least, that's what my mother always says." you add with a wink.

🐸 he complains to you about the whack job in tech support that keeps talking about ghosts & insisting that he's seen dean somewhere before.

🐸 you also knew about his decision to put in his notice even before "mr. adler" did. why? because he'd gone to you first, looking for advice—wanting your opinion. you'd told him that if he wasn't happy, or felt that he needed to be doing something else, that he should go for it. & if he ever missed any part of what he was leaving behind, he knew where to find you ;)

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