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deantfwinchester · 3 days ago

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Love Me Right

Part 1: Henrietta’s

Pairing: ConstructionCEO!Joel x Waitress!Reader

She's eventually gonna be a teacher again bc let's be real, i'm a one-trick pony.

This is a Millionaire Joel AU x Most Eligible Bachelor Trope

Summary: Joel Miller, CEO and Co-Founder of Miller Construction, hasn't been dealing with an Empty Nest very well. His family and friends have tried their best to cheer him up since Sarah left for college in the fall, but the storm cloud above his head remains. On top of that (or perhaps because of it), he has just been named one of Austin's Most Eligible Bachelors.

What will that mean for the new-in-town waitress he meets in his favorite diner? As far as she knows, he's just an average contractor.

Warnings: age gap (reader late 20s, Joel late 40s); family-centered trauma and conflict; lethal levels of fluff otw

A/N: Bear with me for this one y'all. My imagination is ambitious and my brain is obstinate. Title inspired by Sabrina Carpenter’s Short ‘n Sweet - bc i can’t stop fckn listening to Juno 🫣

Word Count: 4.6k

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“Tommy, there ain’t a chance in hell that’s gonna happen. Why on earth did you bring this to me?”

“Well they talked to Joanna at the front desk first. She said wasn’t going to bring it up to you, but I couldn’t just let it slide,” Tommy raises his eyebrows at Joel, shooting him a mischievous look. “Because one - I wasn’t gonna pass up the chance to see this look on your face, and two - would a little publicity be so bad?”

“Who in their right mind is gonna choose a fuckin contractor from the goddamn ‘society pages’?” Joel bristles at his brother’s amusement with an unwavering scowl.

Tommy stares right back, but the playful nature of his expression is unmarred. “Most men won’t Joel - but their wives will.” Tommy’s salacious grin is damn near wider than Joel’s ever seen. Christ, he’s loving this.

“You gotta be kiddin’ me,” Joel says plainly, rolling his eyes.

“Come on brother, think about it - plenty of busy men in this city with bored housewives in need of a project. He tosses her a few thousand to redo the dining room - well who’s gonna do the job? She hasn’t got a clue where to begin and then BOOM! She sees the list of Austin’s Most Eligible Bachelors in the paper - where she finds a photo of the distinguished CEO and senior founder of Miller Construction—”

“Senior, seriously?,” Joel deadpans at him. Tommy ignores him, continuing to wax poetic.

“And can’t help but wonder if the rest of his staff is as dashing as he appears to be,”

“Flattery’s cheap Tommy.”

“Of course then she meets with me and the deal is sealed.” Tommy smiles smugly now that his story is complete.

“Boy can you paint a picture,” responds Joel, rolling his eyes at his brother’s antics. “So you wanna parade me around like a two-bit hooker, huh?

“Whaddya say — can I give ‘em a call?”

“If you’re so hell-bent on ‘marketing’ why don’t you do it?” Joel says flippantly.

“Well I’m not a bachelor anymore, am I?,” he grins brightly at him. This time, it’s sincere.

“Don’t break your arm pattin' yourself on the back, Tommy. Maria mighta said yes, but there ain’t a ring on your finger yet. She’s still got a few months to wise up,” Joel challenges, his tone playful.

Tommy glares at him, but then gives a sobered nod. “You’re right about that. I know I’m a lucky fucker, and I’m not interested in testing that luck - even for a charity auction. Sorry to the dogs, or the food bank or — is it old people?”

“Hell bent on it, and don’t even know what it’s for? Christ - it’s a Make-A-Wish thing Tommy, damn,” Joel replies, looking bewildered at his brother’s callous and cavalier response.

“And isn’t your attention and concern for the bigger picture just what they need in volunteers?” Tommy retorts, expression still smug but eyes hopeful. “What, ‘s it gonna kill you to go out for once? It’ll be a formality at worst and maybe even a good time if you loosen up a bit.”

“I can think of a number of other ‘worsts’ than a formality,” Joel muses

“You’re gentleman enough to handle it just fine,” Tommy continues.

It has been quite a while since Joel’s been out of his house for much other than work or routine, and even longer since he’s been out with anyone other than Tommy, Maria, and the guys from work here and there. He’ll admit, he hasn’t been dealing with an empty nest very well. He’s done a pretty terrible job of keeping busy since he dropped Sarah off at school back in the fall. She’d gotten in exactly where she’d hoped, and made friends fast - for this he was over the moon - but he misses her like crazy. He’s been swimming back and forth in swelling pride and stabbing grief since September, ecstatic and aching all at once. He knew Tommy’s intentions were relatively pure, business interest aside. He knows they’ve been worried about him for a couple of months now - they haven’t exactly been subtle — they’d started having him over for dinner damn near once a week.

This newfound hobby of Tommy’s, cooking like a grown-up, had become the ruse en vogue for getting Joel out of his house. As Maria’s caseload grew at the law firm, Tommy wanted to make sure she had a real meal to eat when she finally got home — so he started cooking. Joel had to admit it was real sweet, watching his brother dive headfirst into learning a new skill just to take care of his bride-to-be. He claimed it only made sense with his far more flexible schedule, but Joel knew it made Tommy proud to be able to do this for her, and the very fact he wanted to made Joel proud as well.

Once Sarah left for school, however, Tommy quickly discovered his brother’s less-than-satisfactory habits of microwave dinners or forgetting to eat in general. He was a fair chef in his own right once upon a time, but without his little girl there to feed, bothering to make a balanced meal fell by the wayside. Joanna, a kindly woman in her seventies, had been one of the first to notice the change in Joel’s demeanor and the drawn nature of his features. Not much younger than the boys’ mother would be today, Joanna worked at the front desk of Miller Construction, greeting clients with a maternal warmth that, Tommy had to admit, was in part strategic. Disarm a client while they wait with a smile and you’d be able to pry open their hearts and their pockets.

Joanna was not unaware of the role she played in this game, though she did not approve. She’d informed Tommy of her concern for Joel, and the regular dinner invitations followed suit. This, accompanied with Joanna’s tugging Joel along to a nearby diner for lunch a couple of times a week in November had practically pulled Joel through the fall slump and into the new year. The holiday visits home from Sarah had helped a great deal, as well.

Joel wasn’t blind to his friends and family’s kahoots to help him through this patch. Though he sometimes grudgingly obliged to Joanna’s pestering him out the door because she hadn’t “seen you eat a bite all day. Four cups of black coffee don’t count, and you know it. Up!,” or Tommy’s employing Maria to send a text herself inviting him to dinner after he’d tried and simply received the finger, he was grateful for their efforts and care. Sarah was too, but he didn’t need to know that. Those lunchtime diner visits soon turned into breakfasts — a preemptive measure on Joanna’s part to add some time out in public to Joel’s routine of home — office — work site — home. Eventually she’d pavolv-ed him into it, and Joel was at the diner for coffee, breakfast, and one of the only physical newspapers left in existence every Monday, Wednesday, and Friday, at first following behind Joanna and eventually on his own.

Joanna had been with the Miller brothers since the business was far smaller, just a few years after its inception, when they started needing a receptionist/secretary/assistant, just someone who knew how to manage their slowly growing demand. She’d been a friend of their mother’s and had taken up some of the slack when she’d passed, grieving alongside her friend’s sons and looking after them in her wake. She’d been one of the only reasons Joel and Tommy had been able to build the tiny Miller Bros. into its current position as Miller Construction, multi-million-dollar contracting firm, and the largest in the Austin Metro area. Joel’s practical thinking and creativity combined with Tommy’s ambition and idealistic hopes of grandeur got them into successful meetings with investors that Joanna quietly set up via her husband’s business contacts. Their vision reminded her so much of their mother’s optimism she couldn’t help herself. She’d keep an eye on Sarah when Joel needed and ensured they were taken care of in the moments they would have needed their mother around.

As the boys’ surrogate mother figure and Sarah’s Aunt Jo, it came as no surprise that amid Joel’s season of empty-nested loneliness Joanna had begun encouraging him to “get back out there” and claimed that she “won’t be around forever” and “would like to see him settled before I go.” Classic maternal guilt-tripping, and Joel told her each time that he hears 70 is the new 50. She told him to try that again in a few years when he hits the real 50.

Truth of the matter was, Joel had been alone for a long time. He’d seen people on and off while Sarah was growing up, but it was a rare occasion, and no fling had ever lasted more than a couple of months. With Sarah at home, it never mattered much to Joel — he had someone to care for who was the best company he’d ever had right in front of him. She’d needed him a little less as she’d grown up, but he always had a purpose.

Joel was a natural-born caretaker — between brotherhood and fatherhood, he took to it like a tadpole to water. With Sarah away at school and his little brother engaged, however, he couldn’t figure out where to put all that love, and so it crackled into grief like a blackening candle wick, blooming into a flower of ash that nestled in his chest. The cloud of soot hovered around him for a while as he went through the motions of his everyday. Tommy, Maria, and Joanna all wanted to see him find his way again, as did Sarah when she received honest reports from her family members after some prodding. He always put on his biggest smile for her, never wanting her to worry, but she could see something hurting in his eyes, just below the surface.

While it may have been blatantly out of his comfort zone, Tommy and Joanna jumped at the opportunity to convince Joel when the Most Eligible Bachelors’ Auction came knocking. He needed something to disrupt his routine, with the added bonus of his coming out into the social scene like a plaid-clad debutante with a few extra crow’s feet.

After rolling the last few months’ events around in his mind for a couple of minutes while Tommy answers a phone call, Joel is broken from his reverie. Tommy’s standing in front of him again, waving a hand back and forth.

“Hey ground control - you with me?,” he asks before Joel’s eyes focus on him once again. “Can I give em a call?,” and this time Joel notices the concern in Tommy’s eyes as his joking facade flickers with hope. It’s more than just publicity, and he owes it to them to give it a shot.

Joel releases a measured sigh, relenting. “Can’t believe I’m saying this but sure, fuck it. Call ‘em back,” he says rolling his eyes, resigning himself to whatever nonsense his participation will entail. He reminds himself it’s for charity, and returns to his computer, refocusing on his work as Tommy darts out of his office to return to his own, reporting his success to Joanna along the way.

_______________________________________________

You got lucky with this job at Henrietta’s, with its flexible hours and fairly livable wage, you had time to settle into your new place and get to know the city. You spend your off days wandering around, doing research on local schools and prepping your applications for summer school and the new year.

Never had you pictured yourself leaving students mid-year, and having to do it hurt like hell. You missed the kids you left behind every day, but when a friend caught wind of an acquaintance needing a subletter for a little studio within your price range, you didn’t have much of a choice. You needed to take up the lease starting in January, or you’d be starting over at square one. It had been a long time coming, this encroaching need to run and start over somewhere new. Staying in your hometown was no longer an option — work may have been a saving grace, but the other areas of your life were suffering. You knew healing couldn’t begin without separation. You needed to be far away from everything — it was the only way you could picture trying to feel whole again. Grad school had ended the previous year, so you fled.

With each mile you put between you and your family, you started to feel like your lungs could fully inflate once again. The oppressive air of scrutiny and memory that swam around you at home dropped off piece by piece with each passing mile marker. You’d put a few states between yourself and your parents once it was all said and done, and while it was scary, starting from scratch all over again, it was invigorating. You’d done it at eighteen when you left for college, you could damn well do it again with eight years’ more life experience under your belt.

You’d walked into the diner on your second day in the city. You had some money saved up from time living at home, but knew it would dwindle quickly with rent to pay and no salary coming in on the regular. You would need something to keep busy and pay for necessities until the end of the spring semester. When Diane, the manager caught sight of you, bright-eyed and looking like a deer in headlights, she welcomed you with a warmth you’d only read about in books. She interviewed you then and there and offered you a job on the spot, waiting tables on the breakfast and lunch shifts at least four days a week. She told you your “sweet smile and wide-eyed look will do wonders for you in tips, precious!” You think it’s probably just teacher face you can’t shake, and hope she’s right — maybe it could do you some favors until you get back in the classroom where you belong.

Diane’s rounded face was accentuated with wonderfully deep crow’s feet and smile lines that suggested a lifetime of sharing this warmth, and her dark hair streaked with gray around her hairline and temples rested atop her head in a frazzled bun. She made you comfortable out the gate, and had set you up with a uniform immediately. More aptly, she handed you a t-shirt and an apron to go over your leggings. You were thankful for the relaxed dress code, knowing plenty of other establishments required a much more specific ensemble. Once you’d changed she introduced you to your shift lead, Reggie, and the line-cook-on-duty, Tony, patting you comfortingly on the shoulder and insisting they welcome you, hoping to keep you around to solve their persistent staffing issue.

While Diane was quite a bit older than you, somewhere in her mid-fifties, Reggie and Tony were younger, floating between mid-thirties and early forties, if you had to guess. Reggie was a slim black man you’d put in his thirties, and he greeted you with a smile and an exclamation that he was more than ready to gossip ad nauseum with someone so much closer to his age. He’d been the one to fill you in on Diane’s immediate taking to you, letting you know with little ambiguity that you were just a few years younger than Diane’s daughter, who had moved out of the city about a year ago, and that you favored her to boot. Reggie had called this particular gossip session your orientation.

“Don’t get me wrong honey, Diane’s a sweetheart. But never have I seen her offer a position on the spot. I think having you here may do her some good,” he’d said, before turning to fill you in on Tony the line cook. “Yeah Tony’s hot, but he chain smokes like a chimney and doesn’t care at all when I ask him to keep his second hand smoke to himself on the days I have a performance!,” he shouted pointedly at Tony, who only looked up long enough to give Reggie the finger and wink at you. Tony was a muscular Italian guy in his forties with tattoos of a sort that didn’t quite match up with the gold chain and cross pendant hanging around his neck. When your eyes went wide at the wink, Reggie giggled a bit and leaned toward you. “Don’t worry, Tony’s a little sleazy but harmless. He’ll hit on anything in a skirt, but as soon as you tell him you aren’t interested he’ll back off and won’t bring it up again. He’s a good guy, but don’t tell him I said that.”

Over the course of your shift you discovered that Diane’s been at Henrietta’s for fifteen years, Reggie is a drag queen and lounge singer by the name of Wizz Tiria at a few different clubs around town, and Tony has a few other business ventures he mentions on and off (the details of which he keeps to himself), but never misses taking his Mom to church on Sundays. You share a good bit about yourself as well in exchange — what brought you to Austin, why now, and where you may go from here. It doesn’t take long for you to make yourself at home among this eclectic little bunch, and for the first time in a really, really long time, you’re content with the peaceful monotony of these early winter days.

_______________________________________________

It’s a brisk February morning when you walk into the diner for your shift. You’ve spent the last month working in the cozy little greasy spoon, so you’re still getting to know the regulars, but you’ve caught on pretty quick. You’ve been working the Tuesday, Thursday, and weekend shifts, but when Diane loses another server, you’re eager to pick up the slack — extra pocket change and keep your mind busy. The company’s pretty good too. Thus, you find yourself walking into the diner at 7 AM on a Wednesday morning with a hoodie over your t-shirt and a scarf to ward off more of the wind cutting into your cheeks. You head to the staff room to remove your hoodie and don your apron and emerge, finding the diner a bit colder than it had been up to this point. You’d kept a light jacket or a cardigan on you previously, but today’s need for something heavier led you to selecting a favorite hoodie to throw over your work t-shirt — which you didn’t quite think through until you came into the dining room and felt a chil run up your spine. Diane catches sight of you before you can still yourself.

“Sweetie, what on earth fo you think you’re doing?,” she asks like you’ve done something obviously egregious.

“Huh? What is it?,” you ask innocently, but you know the answer. She can probably see the goosebumps you feel rising on your arms.

“You need somethin’ on under that, you’re gonna freeze in here today!,” she chastises.

“Yeah, I brought my hoodie, but forgot I’d be taking it off. It’s not so bad in here, I’ll be alright,’ you tell her reassuringly.

“Absolutely not. Wait, hold on a second - REGGIE! We got any more o’ those long sleeve souvenir shirts in the case?!” she hollers after him.

“Hold awn!,” he hollers back, Southern twang taking center stage when he yells, just like the rest of them. After a few seconds he emerges with a few in hand. “Got a few left. Ugly as hell, probably why they’re still here. Watcha need ‘em for?”

“Sweetie, go on and change into that before the rush starts. Not the staff shirt, but the branding’ll be fine in case Jason drops by,” she says, rolling her eyes. She pats you on the shoulder, nudging you toward Reggie to take one of the shirts. They’re bright green with a gaudy design on them that makes you laugh when he hands it to you. Jason’s the owner of Henrietta’s, and so you’ve heard, the bane of Diane’s existence. You’ve only heard tale of this rotten Jason thus far, never quite laying eyes on the mythical beast. You really hope today in this goofy shirt isn’t the day you do.

You return to the dining room a few minutes later clad in the neon green monstrosity, tugging at it in a futile effort to make it look better. “Happy now, Diane?!,” you holler as you enter, only to find her standing directly in front of you at the hostess stand, face to face with a man you’d never seen in here before — who you almost run right into, not looking where you’re going. He’s tall and broad with dark brown curls laced with grey streaks, and gray patches in the short beard that frames his jaw. He catches you when you nearly bump right into him, and you look up to meet the deepest brown eyes you’ve ever encountered. Your cheeks go red when you realize what you’ve done.

“Whoa there,” he says, smiling down at you as you stutter out an apology. “It’s alright, no harm done,” he responds, voice gentle but deep. It’s true, he didn’t even budge when he caught you, and you’re fairly certain if you’d fallen, the outcome would’ve been the same.

“Sorry about that Joel. C’mon, your table’s ready,” she says, patting Joel’s arm and leading him forward, not before turning back to you and saying, “Certainly am. Now go grab some coffee for Table 7 for me, will ya sweetie?” with a smile. You’d just run almost smack into a customer, and she wasn’t upset with you or anything. You shouldn’t be surprised, that’s just Diane, but you’re used to much larger reactions to small mistakes. You just nodded and breathed a sigh of relief, but your eyes are drawn once again to the man she’s leading away. He’s looking back at you with a smile that sends a shiver down your spine, one you’re certain has nothing to do with the chill in the air this time. He’s wearing a plaid button-down and a utility jacket, with cheeks and a nose tinged pink from the cold. You tear your eyes away anxiously and head for the coffee pot.

You’ve got your hand around the decaf pot, pouring another cup for the regular at the bar counter, when your eyes find Table 7, your next destination. You see the man, Joel, Diane had called him, with his back to you, facing out the window, newspaper in hand. You steel yourself once again, switch coffee pots, and head for his table.

You approach from the side, hoping not to spook him as he’s engrossed in the paper he has in hand. Christ, when was the last time you saw a physical newspaper? It’s kinda cute, you think, seeing someone reading one on a cold morning with a cup of coffee. So picturesque. Especially someone as handsome as he is, and you find yourself staring at his broad shoulders and dark curls again before he looks up from his reading.

“Hey,” you start, a little shaky, “sorry again, about before. Don’t know what I was doing, not looking where I was going,” you smile a little, shaking your head at your mishap.

“Really, it’s fine. You seemed, uh, preoccupied,” he says, looking down at the offending design on the tshirt you’re wearing, before looking back up at you. “It’s certainly a change from the regular uniform, huh?” he says, smiling at you. The way his eyes crinkle as he does plants a warmth in your chest you aren’t expecting. It’s been so long since you felt it, it’s almost unfamiliar. Your cheeks warm as you smile back at him, hoping it comes off as embarrassment from your wardrobe rather than bashful attraction. You’re about to tell him it’s certainly not a permanent solution, when he speaks again. “So, Sweetie, huh? Haven’t seen you around before — that what they call you in here?” he questions, smirk playing at his lips.

You laugh in response and introduce yourself, and tell him this isn’t your normal shift, but you’ll probably be around for it moving forward. You take his breakfast order, and tell him you’ll let him get back to his paper.

You don’t converse much more when you bring Joel his breakfast, just quiet thanks when you refill his coffee cup. He looks so peaceful, you almost hate to interrupt each time. You ask Reggie about him when you both have a minute behind the counter.

“Yep, that’s Joel. Gorgeous, isn’t he? Started coming in a few months back with an older lady, then more regularly by himself. She’s with him once in a while, kinda seems like a mom vibe, but she doesn’t look like him. Anyway, I think he works construction or something, always coming in with those boots on looking like a lumberjack,” Reggie says flippantly. “Heard from the older lady one day when he was in the bathroom — his daughter went to college back in the fall, they’ve been trying to get him out ever since,” he said, looking sympathetic at the thought.

You feel your heart do a little squeeze at this newfound tidbit. A fresh empty nester. You know how hard it’s been for Diane, so much she’s taken to parenting the staff in her daughter’s stead. Staring at Joel’s back as his head is bowed reading the paper, you begin wondering more and more about him. His daughter’s probably around eighteen, so how old is he? You’d guess he isn’t married, and you didn’t see a ring. Who is he? Why does he come here to read his paper each day? And most importantly — how soon can you find out the answers to these questions? You don’t want to ambush him at all and scare him off, but you’re drawn to him, and so very curious.

Meanwhile, Joel is stealing glances at your reflection in the diner window in front of him, watching you laugh with Reggie and the customers at the bar, smiling sweetly when someone makes a request of you. He needs to get out of there before he starts feeling creepy, he thinks. He rises and walks to the counter to settle his bill with Reggie at the cash register, glancing at you when he does so, futilely trying to balance showing interest and being weird. He leaves a nice tip in the jar for all of you to share, but just before he turns to go, he looks back at you, locking eyes.

“Oh uh, Sweetie?,” he says, smirk on his face. He looks almost bashful when he speaks next, like he’s working up the courage. “Glad you’re picking up. Look forward to seein’ you again,” he smiles. The look on his face when he says it is so sincere, you could melt on the spot. He was nervous about his joke, you could tell, but recovered when you laughed in reply.

“Looking forward to it too, Joel. Enjoy your day,” you say, smiling wide in return. He gives a little wave to everyone before grinnig down at his shoes and walking out of the diner into the crisp February air. Your eyes follow him out to the pick-up he hops into, before looking back over to Reggie and Tony, staring at you devilishly.

“And I’m looking forward to seeing this story unravel,” says Reggie, looking over at Tony and grinning, like something juicy has just unfolded before their eyes. The two are laughing while you smile and wave them off, wiping down the counter. Diane emerges from the office at the sound of their hearty laughter, reading glasses slipping down her nose, notepad in hand, and stares back at the three of you.

“What’d I miss?!,” she asks. You’re smiling too much to respond with anything genuine, so you return to your wiping, and let Reggie take the lead.

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