#also i have like my third migraine this week and my Polite Face is struggling

[caput-medusae]

my coworker is telling me this story about how one of her neighbors took her outdoor cat while she was gone on vacation and i am biting my tongue so hard not to scream about how it wouldn’t have happened if she kept her damn ecology-destroying invasive species indoors

[imagineteamfreewill]

A Good Kind of Not Okay

Title: A Good Kind of Not Okay

Pairing: Nanny!Reader x Director!Sam

Word Count: 4,414

Warnings: A little bit of pining

Square Filled: Director!Sam

Summary: Sam is a single dad who also happens to be one of the world’s most famous movie directors. When he struggles to care for his daughter like he wants, he hires the reader to help care for his pride and joy.

A/N: This is a submission for the 2020-2021 SPN AU Bingo (@spnaubingo​). Please let me know what you think. Enjoy!

X

_______________

Sam was running late. Again. Filming was behind schedule for the third time that week, and as the director, he had to stay until everything was finished. Of course, he was part of the reason why the filming was behind schedule. He couldn’t help it. Sam was a perfectionist, and he always had been. That’s what got him hired.

“I’m so sorry I’m late,” Sam said. He glanced down the street and then turned. “I’m on my way, I should be there in ten minutes.”

“Mr. Winchester, we’ve talked about this.”

“I know, I’m sorry. I’ll be there soon.” He ended the call before the center director could chew him out any further. He felt bad enough as it was, he didn’t need more reminders and warnings about being late. He really did try to keep a normal schedule, and he always made arrangements if the filming was scheduled to go late into the night or early in the morning, but there were some things that were out of his control.

The roads were blessedly empty and Sam pulled into the parking lot in just over five minutes. He wasn’t normally one to speed, especially if Elsie was in the car with him, but it was times like these when he was thankful for the extra horsepower. The Charger was the last big thing he’d bought for himself before his daughter was born and he rarely took advantage of its capabilities. Dean constantly nagged him about it.

Climbing out of the car, he grabbed his phone from the cupholder and rushed inside where he knew Elsie was waiting. The day care was completely deserted except for her and the director, who was sitting in one of the waiting room chairs, alternating between watching the front doors and the small child perched at the plastic drawing table beside her. Even the lights in the back playrooms and the office were off.

“Mr. Winchester, I’m glad you made it here okay.”

“Daddy!” Elsie bolted from her chair, abandoning her backpack and leaving the crayons to roll off the table and onto the floor. Sam crouched to scoop her up as soon as she was in arm’s reach, and his daughter immediately wrapped her arms around his neck and pressed her face against his shoulder. 

“Hey, sweetheart. I’m sorry I’m late,” he murmured, and he cradled the back of her tiny head in his hand. He still couldn’t get over how tiny she was, even at four years old.

The director stood from her seat, clipboard and radio in hand. She gave him a scolding look. “Mr. Winchester—”

“Please, call me Sam,” he interrupted. “And I know, you can’t keep waiting with her. It won’t happen again.”

Her expression turned withering. “That’s becoming a catchphrase for you. I’m sorry, Mr. Winchester, but Elsie can’t keep coming to Gilded Hearts after the end of this week. We have very strict policies about parent pick-up and you signed a contract agreeing to uphold them. You’ve broken that contract multiple times this week alone, and I can’t count the number of times you’ve broken it otherwise.”

Sam frowned, shifting Elsie in his arms so he could pick up her backpack with one hand. “You’re kicking her out? Please, don’t kick her out just because I messed up a few—”

“It’s been more than a few times,” the director pointed out. “If it had been an emergency, it would be a different story, but we can’t keep staying late with her because you can’t seem to be able to pick her at the time you agreed upon when Elsie first started coming here.”

Lifting her head, Elsie looked up at Sam with big, hazel eyes. She’d perfected his own puppy dog expression solely to use on Sam and her Uncle Dean, and Sam’s heart sunk. The guilt settled in and suddenly all he could think about was how selfish he’d been. He’d been putting work in front of his daughter, something he promised he’d never do, and now he had to face the consequences.

“Okay. You said the end of this week?” Sam asked, sighing. The director nodded and gave him a polite, albeit tight, smile. “Alright. Thanks for staying with her. Have a good night.”

The director waved goodbye to Elsie, then watched in silence as Sam carried her out to the car. It was still sunny out and Elsie squinted, whining a little when he stepped out of the shade provided by the enormous oak trees that guarded the day care’s entrance.

“I know. Your sunglasses are in the car, honey.” Sam dug his keys back out of his pocket and unlocked the backseat, then carefully situated Elsie in her carseat. The tiny pair of Minnie Mouse sunglasses were right where they always were, and once his daughter was buckled in, he handed them to her so she could slip them on. She did so immediately.

“Are you sad, Daddy?” she asked. Elsie reached out a hand, grabbing onto Sam’s coat before he could back out of the doorway and go around to the driver’s side.

“I’m not sad, babygirl. Daddy’s just tired from work. Are you hungry? You ready to go home and eat?”

After a moment, Elsie nodded and let go of his coat. Sam shut the door and let out a long sigh as he went around the back of the car. His head was pounding and he was exhausted from shooting in the heat all day, but getting food in his little girl’s stomach and making sure that she got everything else she needed before bedtime had to be his priority right now. Then he would have to figure out where she was going to spend her days after the week was over. She couldn’t exactly come to work with him on an R-rated movie set. The impending migraine would have to wait.

_______________

“What’s your name?” the little girl asked, and you raised your eyebrows at her for a brief moment, then crouched down to her level.

“I’m Y/N. What’s yours?”

She held onto the door handle with both hands, swinging her weight on it as she stared at you. “I’m not supposed to tell strangers my name.”

“That’s very smart,” you replied, smiling. “Is your daddy home?”

“Who’s asking?”

A laugh almost slipped out at the cliché response, but you carefully held it back. You started to answer when a very tall, very handsome man in a suit stepped up behind the little girl in the tutu.

Nodding, you stood and held out your hand for him to shake. “I’m Y/N, from the nanny agency. Are you Mr. Winchester?”

The man smiled politely and shook your hand before reaching down to scoop up Elsie. He held her on one hip and stepped aside, gesturing for you to come in. He didn’t even seem to be bothered that his shirt and jacket were now rumpled from being squashed by the little girl and her very fluffy tutu, nor did he seem phased when she reached out to hold onto the tie around his neck.

“It’s nice to meet you, Y/N. Please, call me Sam. I’m glad you could come on such short notice.”

“It’s not a problem,” you replied. You glanced around the entryway of Sam’s enormous house, a little surprised. It was grand, but compared to some of the others in the neighborhood, this house seemed more… lived in. Turning around, you smiled politely. “Is there anything you wanted to ask me that wasn’t in my file? I know that they already sent over my resume, references, and bio, but there’s always something that people want to know.”

Sam gave you a once-over before closing the door. “You’re a live-in nanny, right?” he asked. You nodded. “I don’t have any questions, but how about you check out the guest room before you decide if you want to stay? The last nanny we tried had some issues with it.”

“Issues?” you repeated, suddenly a bit more hesitant, and Sam gestured for you to follow him up the stairs. You did, glad that you’d left your suitcase in the car. The staircase was immense and it would’ve been a pain to drag it up all the way.

As you walked, Elsie chattered to Sam, who glanced at her and replied when necessary. You couldn’t hear everything they said, but it was clear that he cared deeply for her. Every nod, every thoughtful reply, every second of eye contact he offered her reassured you that this would be a good family to work with for your next position. It would certainly be better than your last one, that was for sure.

When you finally arrived at the opposite end of the hallway, Sam pushed open a door and gestured for you to enter first. You did, taking a look around. The “guest room” was more like a deluxe suite and you had to remind yourself not to let your mouth hang open as you took it all in. It made you wonder if there was some sort of housekeeper or maid that cleaned Sam’s house, because there was no way he kept the room as beautiful as it was, worked, and took care of his gorgeous little girl.

“It’s got an attached bathroom with a shower and a tub, and you’ll have your own private balcony. It overlooks the backyard and the pool, which you’re welcome to use at any time. There’s a walk-in closet through that door,” Sam pointed to a closed door off to the right of the bathroom, “And there’s an office across the hall you can use if you want. There’s a printer and internet hookups in case you’re having problems with the WiFi. You shouldn’t, but it never hurts to be prepared. Of course, if you don’t like the furniture I’ve got in here we can move it and you can put your own things in. I hired a decorator for the whole house when I first moved in and I haven’t done anything with the room since then.

You nodded, a bit overwhelmed. “Right. Can I ask what the issue was? That the last nanny had?”

“She didn’t like the view from the balcony, apparently, and she complained that she was too close to Elsie’s room.” You frowned and Sam shrugged. The distaste was clear in his voice as he continued, “She said she preferred to have a room near the other adults in the household instead of the child that she cares for. My room is on the other side of the stairs we came up.”

Elsie started to wiggle in his arms and he set her down, not looking away from you. She instantly ran over to the bed and climbed on top to sprawl out over the plush white comforter.

“The room is great, Sam,” you replied, nodding. “It’s amazing, actually.” You glanced back at Elsie and sat on the edge of the mattress. “How’s the bed? Comfy?”

Elsie giggled and nodded before rolling onto her stomach to look at Sam. “Is this my new nanny?”

“I think so,” Sam replied. He looked over at you and you nodded. “Looks like it, Elsie girl! You can show her your room and your playroom in a few minutes, okay? First we gotta do the grown-up stuff.”

Grinning, the little girl scrambled off the bed to run off to another part of the house. She shouted a quick “Okay!” on her way out of the room.

“So, you think you’d be okay being her nanny? Obviously I’ll let you look over the contract and you can take it to a lawyer if you need—”

“That’s not really necessary,” you told him, holding up your hand to stop Sam from going any further. “I’ll look it over downstairs if you wouldn’t mind getting me something to drink while I read.”

“Water okay?”

You nodded, and you and Sam headed downstairs where the contract was waiting.

_______________

Working for Sam was one of the best things that had ever happened to you. Not only was Elsie adorable and one of the smartest, funniest kids you’d ever nannied, but her dad was amazing, too. He never failed to make you laugh and though he was constantly overworking himself during the day, you admired the way that his focus was entirely on Elsie and his homelife as soon as he parked in the garage. Even if he finished work at three in the morning, he came looking for his daughter the minute he was home. If she was awake, she was always more than happy to cuddle up and watch a movie, go swimming in their pool, or just show him the pictures she’d worked on for him during the day. Then, as soon as the little princess was in bed, Sam’s attention turned to you. That was one of the best parts of your job, though it was becoming a problem. No matter what Sam did and despite your best efforts, your crush kept growing. He was just too great, and you worried that someday you’d be heartbroken when he brought home some gorgeous movie star. Then you’d have to quit, and not only would you be out of a job, but the best two people in your life would immediately become a part of your past. That was the last thing you wanted.

It wasn’t until you’d been the nanny for eight months that Sam asked you to bring Elsie to set. The request caught you off guard—usually he avoided involving Elsie in anything that had to do with his work because of the nature of his films—but you knew that he was a smart guy, so you loaded up the almost-five-year-old into your car and drove to the address he’d texted.

“Daddy!” Elsie squealed. Sam’s head turned towards you and he smiled wide when he saw Elsie dragging you by the hand across the packed dirt of the filming site. She had insisted on wearing her princess dress, and the sight of her in the poofy, sparkly dress and Minnie Mouse sunglasses was enough to make anyone laugh. You were thankful you’d put your own sunglasses on before you’d climbed out of the car, otherwise the sun’s glare would have been too bright for you to even see Sam. He had his glasses on as well, and you briefly wondered if he’d take them off at some point so you could see his eyes in the sunlight.

“Hi, Bug!” As soon as she was within his reach, Sam picked her up and swung her up onto his shoulders. The move was almost one fluid motion and though he did it all the time, you still marveled and Elsie still giggled.

The man Sam had been talking to—you vaguely recognized his face from a magazine in the grocery store checkout—was dressed in an elaborate suit of leather armor. He glanced over at you as you approached, but he quickly turned his attention back to Sam.

“So what are you going to do about her?” the man asked.

Sam glanced at him before looking up at Elsie, smiling wide. “We’ll have a talk. Don’t worry about it, Erick.”

Ah, so he’s the action hero, you thought, and you looked the actor up and down. He looks shorter in person.

Erick turned and caught you staring at him, and his lip curled up in disgust. “Who are you?”

“She’s my best friend!” Elsie replied before anyone else could. You smiled on instinct.

“Right...” Erick drawled. He looked up at Elsie and the disgusted look on his face didn’t fade even as he walked away to a u-shaped cluster of chairs and makeup vanities. He was immediately swarmed by women fussing over his hair, makeup, and costume.

Once he was fair enough away, you turned towards Sam with raised eyebrows. “So. This is the movie business,” you retorted.

He laughed and adjusted his grip on Elsie’s little legs. “Something like it, yeah. Don’t worry about him, he’s always like that. It’s not one of his redeeming features, but he was the favorite for this role. Do you guys want a tour of the set?”

Elsie cheered and wiggled a little on Sam’s shoulders, and he tightened his grip accordingly. You nodded in agreement.

“A tour would be great, Sam, but aren’t you on your lunch break?”

Sam shrugged and started walking. You followed close behind as he began to explain the set in terms that Elsie could understand. She was smart, and she loved big words, but she was still just a kid. After a while, he managed to commandeer a golf cart for the three of you, and you ended up riding around not only just the set, but in between all the trailers and the service roads that surrounded the site. You had to admit that the area was beautiful, even if it was hot and dusty.

Eventually, you, Sam, and Elsie ended up outside his trailer. It was smaller than the actors’, but he explained as you followed him up the steps that he really didn’t use it much, and he only had one for this part of production because they were filming in a more remote location than usual. Food was waiting for you on the small dining table inside, and all three of you breathed a sigh of relief at the air conditioning.

“Can I come to set tomorrow?” Elsie asked as she climbed up onto the couch.

Sam handed her the hot dog from the container marked with her name and smiled a little. “Not tomorrow, Ells. Maybe another day,” he said. He picked up the two remaining containers and held out the one with your name scrawled across the top.

After murmuring your thanks, you settled down on the opposite side of Elsie from him and opened the styrofoam box. Your favorite sandwich was inside and you smiled over at Sam, a little bit surprised that he’d remembered. He didn’t make or order you food often, since you normally ate with Elsie during the day and on your own at night so that Elsie’s attention wasn’t divided between the two of you.

“You mentioned that it was your favorite that one time we went to the boardwalk,” Sam said, noticing your surprise. “It just kinda stuck in my brain, and I saw it on the menu when I was ordering our lunches before you got here.”

“I can’t believe you remembered that,” you replied, honestly shocked. No one had ever remembered your usual order. “Thank you.”

Sam nodded in reply and the three of you dug into your meals in relative silence. Elsie finished first, like usual, and she was starting to dig through the things in Sam’s trailer when there was a knock at the door.

Elated, the little girl ran over and tugged it open, the force of which pushed her down to sit on the top step of the entry. “Hi!” she cried, and you sat up on the couch to see who she was talking to.

“Hi!” a woman chuckled. After a second, Elsie popped back up and led the short-haired woman into the trailer by the hand. “Is this your daughter, Sam?”

“No, this is a monster!” Sam grabbed Elsie around the waist and pulled her into his lap, growling playfully. Elsie squealed and squirmed as he tickled her, and the woman laughed. You smiled too, but you reached over to move Sam’s half-eaten meal out of the way. You’d seen this play out too many times to think that he and Elsie would be able to avoid knocking it onto the rug.

Elsie finally freed herself from Sam’s grasp and scrambled into yours. You wrapped them around her, hugging her tightly, and pressed a kiss to the top of her head. Sam caught your eye and grinned wide before looking back at the woman still standing in his trailer.

“What’s going on, Jody? Are we having a wardrobe problem again?��� he asked, getting to his feet.

She shook her head. “No, but I heard a certain someone in here really likes princesses, and I thought I could give her a little tour of the wardrobe trailer,” Jody replied with a slow smile.

“Right, the wardrobe trailer with all the princess dresses…” Sam looked back at Elsie, who was watching him and Jody with wide eyes. She’d cued in on the key words in their conversation and was practically vibrating with excitement in your arms. “What do you say, Elsie? Would you like to go with Miss Jody to see the princess dresses for daddy’s movie?”

Elsie nodded vigorously and you let her down off your lap. She grabbed Jody’s outstretched hand with a wide smile and waved at Sam as she was led down the steps that led out of his trailer. The door slammed behind her and Jody, and after a second, you stood and gathered up two of the discarded lunch containers. 

Sam stared at you as you carried them over to the trash, and finally you looked up at him. “What?”

“Nothing,” he quickly replied, shaking his head. “Nothing.”

“You’re staring at me, Sam. There’s not something on the back of my pants, right? Or shirt?” You twisted, trying to get a look at your back just in case, and your face grew hot at the idea that you’d been walking around with Sam-freaking-Winchester, the super hot, award-winning director, all the while looking like a slob.

“No, no. I just…” Sam sighed, rubbing the back of his neck. He watched through the window as some of the crew members walked by outside, then dropped his hand back down and looked back at you. “We need to talk about something.”

Oh no.

“Sure, is everything okay?”

Sam sat back down on the couch and gestured for you to return to your own seat. You did, and you purposefully folded your hands in your lap so that you wouldn’t fidget and give away how nervous you felt. Your stomach was twisted up in knots.

“Yes. I mean, no, but… It’s a good kind of not okay.”

“Oh…Okay.”

“That didn’t make sense,” Sam said after a second.

“No, it didn’t,” you agreed, smiling a little. “Is this about Elsie? Is there something different you maybe want me to do with her? Or do you think it’s time for her to go back to a daycare, or even a preschool? She’s almost in Kindergarten anyway. I really don’t mind just watching her in the mornings and afternoons, if that’s what you need.”

“Do you not want to work with Elsie anymore?” His eyebrows furrowed and you quickly backtracked. “Because if you don’t—”

“No! No, I love Elsie. She’s an amazing kid, Sam. I just… I’m trying to figure out what you mean. A good kind of not okay?”

Sam sighed and nodded. He leaned forward, resting his elbows on his knees for a few moments as he thought, then leaned back and relaxed against the couch cushions. You watched in silence, and with each passing second, the feeling that you might puke just from the suspense of the whole thing grew.

“I like you, Y/N. I like you a lot,” Sam finally said.

“I like you and Elsie too, Sam, but what’s that got to do with this?”

“No.” He shook his head, reaching over to put one large hand over your folded ones. You froze, absolutely stunned. Sam had never touched you except for handshakes, or maybe in passing when he took Elsie from you.

“Y/N, I really like you. I like you in the non-professional sense.”

Oh.

“I like you in the romantic sense,” Sam continued. “And I’d really like to see you romantically, but you’re my employee. I don’t want to cross any boundaries, and the only reason I’m telling you this is because I think that you might want the same thing.”

You swallowed, looking down. Slowly, you relaxed your grip on your hands and let him take one of them in his. After a second, his thumb began to rub over your skin and the feeling was hypnotizing. “I do. Want the same,” you added. “I’ve liked you a long time, Sam.”

“I don’t want you to feel pressured, Y/N.”

Looking up at him, you shook your head and squeezed his hand. “I don’t. I don’t feel pressured, Sam. I really do like you, and I was honestly worried I’d have to quit if you ever brought home some famous movie star or something. I wouldn’t have been able to handle it.”

Sam smiled wide, his eyes lighting up. “Do you know how long I’ve been wanting to hear you say that?” You shook your head. “A really long time, Y/N. Almost the whole time you’ve been Elsie’s nanny,” he admitted, and you grinned back at him.

Any nerves you’d had were completely gone now. Sam’s touch—even though it was just his thumb on the back of your hand—was more soothing than you could’ve ever imagined, and though the butterflies in your stomach were alive and well, you’d hoped for a while that you and Sam would have this conversation.

“Really?”

He nodded and brought your hand up to his lips to kiss it. The butterflies leaped for joy.

“That’s a long time. I didn’t even catch on,” you told him.

“I had to be careful. And to be honest, the only reason I suspected you liked me back is because Elsie started talking about how you and I act like one of her friend’s parents whenever we’re together. She started asking questions and it made me think.”

You laughed. “That little girl has got a brain bigger than yours. She’s gonna grow up amazing.”

Sam hadn’t stopped grinning at you and you felt your face grow warm under all the attention. If this was an old black and white movie, you would’ve swooned by now, but now his smile was beginning to fade. You sensed that the other shoe was about to drop and your own smile wilted.

“I’ve got you to thank for a lot of that,” Sam said, his voice softer. “We can’t be together if you're my employee, Y/N.”

“We’ll figure it out,” you murmured. After a second, you gave him a sly smile. “You and Elsie just need to put your big brains together.”

_______________

Want to commission a story of your own? Check out the details here.

Want to get early access to content, discounted commissions, personalize stories, and priority when my requests are open? Support me on Patreon by becoming a patron! Find the link in this post or in my tumblr bio.

Want to support my writing with a one-time donation? Buy me a ko-fi! Find the link in this post or in my tumblr bio.

Want to be tagged? Send me an ask! Tag lists include:

Forever, Sam, Dean, Cas, Deaf!Reader, Words Series (Multiple Pairings/Characters), Home Series (Reader x Marine!Sam), From The Dead Series (Reader x Soldier!Dean), Consort Series (Goddess!Reader x Dean), Sam x Meg 2.0, Blog/Series Updates, and Drabble Days/Writing Events

@lipstickandwhiskey​ @riversong-sam​ @shaelyn102​ @gabrielslittleangel​ @supermoonpanda​ @feelmyroarrrr​ @crispychrissy​ @shamelesslydean​ @mlovesstories​ @curlyhairedblueeyedangel​ @5seconds-of-fandoms​ @sandlee44​ @megasimpleplan4ever​ @ellie-andthemachine​ @lucifersbird​ @sev3nruby​ @katymacsupernatural​ @ultimatecin73​ @musiclovinchic93​ @mannls​ @lyarr24​ @fiftyshadesoffandom6783​ @choosemyname​ @mishascupcake​ @alexwinchester23​ @blackcherrywhiskey​ @mrswhozeewhatsis​ @babypink224221​ @just-another-busy-fangirl​ @idksupernatural​ @whimsicalrobots​ @kazkingdom​ @deascheck​ @courtney-elizabeth-winchester​ @fuckmemgc​ @deansgirl215​ @supernaturalharry​ @vallucky-gal​ @reginaphalange2403​ @musicalsarelove​ @thorins-queen-of-erebor​ @witch-of-letters​ @itssierramcquade​ @train-wrecc​ @swirlyoreo​ @jae-sch​ @alliegc28​ @meangirlsx​ @team-free-will-you-idjits-67​