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5 steps to get your boss to date you

Summary:

If anyone asks, it was probably all Dave's fault, but how was he to know that you just had to plant the seed in Chad's head, for Chad to decide that of course there was no reason to not try to woo the man who owns the team they play for.

Notes:

So what do you do when 48 hours before you're due to finish this fic, you start feeling really sick? Do you abandon the idea of finishing it for the deadline, because you're hopelessly behind due to a busy august? Apparently not. So here we are. A few hours before the deadline, and while I won't be able to post every chapter before, I have decided it counts because everything is ready and I just need to give everything one last look.
So I'm really counting on getting the rest of the chapters out within a week, otherwise hunt me down. And if you're counting on me keeping a consistent word count for chapters, well.... that's too bad.

Also shout out to lo_jynx for giving me the original idea of star player Chad and owner of the team Rex, when I was fretting about what to do for this month. It was a (stressful) delight.

Chapter 1: Get him to notice you

Chapter Text

Chad looked like he was in deep thought, as he was staring off in the distance, while he was mindlessly moving the soccer ball between his feet.

He could probably have stood there for a while, if not for the fact that suddenly he felt the nearness of a foot, and then the ball disappeared under him. He turned around in a flash, a 'hey' on the tip of his tongue, if not for the fact that Dave had been the one to steal it from him.

"So what's got you so distracted today?" Dave asked, a teasing glint in his eyes.

Chad had half a mind to not pout in front of his brother-in-law, but he couldn't completely hide it. "Nothing much, just being a bit tired," he said, as he tried to hide the fact that that was very much not the case, as he tried to steal back the ball, but Dave just dribbled a bit backwards with it, trying to bait Chad into following him, which he did.

"Yeah, no, that is not your tired face," Dave pointed out, the smile stretching a bit wider.

"And how do you know that?" Chad tried to counter, but it was impossible. Dave had gotten way too much insight on him, the moment he had started dating Chad's sister, Diego, and he was now suffering eternally from that.

Dave raised an eyebrow. "Come on," he said, and finally let the ball roll back over to Chad's feet.

"It's just..." Chad stopped up, and couldn't stop his gaze from drifting off to look at where he had earlier, to the group of people who were still talking with each other by the sidelines.

Dave's eyes followed Chad's gaze, and when he saw where he was looking, a chuckle escaped him.

"Oh, I see," his tone of voice was a bit too cheeky.

Chad huffed. "No, you absolutely do not," he said as he looked back at Dave.

"I knew you had a good eye on him," Dave said, almost a bit too loud for Chad’s liking.

Chad hissed and shushed him, as he looked around, but their teammates seemed to be as content to ignore actually training as the two of them, and were spread out either lazily playing with a ball, or just chatting around, as they waited for their coach to return.

"Come on, no one is paying it any mind," Dave said with a laugh. "And I don't think anyone would really fault you for thinking that."

Chad shook his head. "That's not the point!"

Dave looked over at the group at the sidelines. They seemed to be starting to come to the end of the conversation, although their coach, who was in the midst of the group, was still making a lot of big hand gestures.

"You don't really hide it as well as you think you do anyway."

"Ugghhh," Chad hid his face in his hands. "I know. I'm terrible. And it's a terrible idea, but I just can't stop thinking about him, and what he could do to me, and what I want."

Dave let out a laugh, which didn't really make Chad feel better about the whole thing. "I mean, part of being on this team was to make sure that you could finally live your life as freely as you wanted, and if part of that is crushing on the man who literally owns the team, who's gonna fault you for that?"

Chad removed his hands slightly, although his face was still very hot, so he was undoubtedly blushing furiously. "How you have a way with words."

"Is it wrong, though?"

Chad sighed and finally completely removed his hands. "No."

Dave grabbed Chad's shoulder. "But you know I am here for you, if you need anything. And that is both if you need help with wooing him, or if you just need a shoulder to cry on. I'm here."

It was strangely sentimental, but Chad did really appreciate it. When he had joined the team he had never imagined being as close to someone as he had gotten to Dave, although there had definitely been a momentarily loss when Dave and Diego had started dating, it never felt like he had been left by either of them, and on the upside, he had only really gotten closer to Diego with Dave in the picture.

But while the sentimentality of it all was good, something else in the sentence struck Chad, and he could feel his face stretching into a smile.

"Why are you looking at me like that?" Dave asked, suddenly a bit more hesitant.

"You're right. I just need to do something about it," Chad said, and briefly gazed over at the group that had finally broken up. "I just need to woo him! Get him to notice me!"

Dave opened his mouth and then closed it again, and then opened it, when he finally knew what he was gonna say, "That was not what I meant exactly," his voice was a little bit quieter.

"No! You were absolutely right! Instead of moping around, I just need to grab the chance," Chad said, his entire face was lit up like a little sun. He truly could feel like this was the answer to all the problems.

Dave couldn't say no to Chad, not when he was looking like that, and while he briefly gazed towards the owner, a certain Rex Roofer, talking on his phone as he was walking away from the field, with his assistant in tow, it just made him realize even more, that this was the best course of action for this crush Chad had had for months now. Either he had his heart broken, and Dave would be ready with that shoulder and possibly ice cream, or Chad would finally find his own person, although Dave thought it was unlikely at this moment.

"Alright, I'll help," Dave said as he looked back at Chad.

Chad beamed back at him.

"But for the record, I do think this is a bad idea if your sister asks!" Dave said.

"Of course, of course!" Chad said and nodded energetically. He was about to vibrate out of his skin as he was thinking over how to go about it.

Dave sighed a bit, but couldn't stop the fond smile on his lips either. "Alright, so what's first?"

"Well, I gotta get him to notice me," Chad said with a determined nod.

At that, Dave laughed softly. "You're our star player. I'm pretty sure he already knows you exist."

Chad felt a bit stumped as he turned it around in his head, not that he got far, since their coach suddenly shouted at them.

"What are you all standing around for?"

Chad and Dave shared a look before they grabbed the ball and trotted back over to him, ready for whatever the coach wanted them to do.



By the time their coach had sent them back to the locker room, Chad was still just as stumped about how to go about it, which was why he ended up using a bit too much power as he shut the door to his locker, which made a few of his teammates look over at him in shock.

"You okay there?" One of them, Mark, asked with a raised eyebrow.

Chad suddenly shrank a little bit under the attention. "Yeah, yeah, I'm fine. Just a bit in my head today."

"Huh... you're usually so well tempered," Mark shot back, which was the exact moment Dave decided to break in.

Dave swung an arm around Chad's shoulders. "He got a bit of a love problem here," Dave said, in a smug voice, as he gave Chad a pat on the chest.

Chad could feel his face heating up again.

But this certainly got the attention of more of his teammates. "Ey, I thought you would die single," Johnny said, who was known as one of their more crass teammates.

Mark stepped forward, a curious glance in his eyes, as he seemed to be suddenly very interested in the conversation. "Who is it?"

Chad wanted to bury himself, because while he wasn't ashamed, he did not want all the teasing this would lead to. "Ah, you don't know them," he lied as smoothly as he could.

"But what's the problem then?" One of the other teammates joined in as well to ask.

Chad scratched his neck, while Dave tightened his arm around his shoulders, obviously in a way to urge him on. "How... how do you get someone to notice you?"

There was a moment of silence, and then laughter broke out in the locker room.

"How do you have problems with that?"

"Of all people to ask that!"

"How can people not notice you?"

"Oh, to be that blind."

And all Chad could do was blink a bit, confused at that, as Dave leaned in and quietly said, "What did I say? You're impossible to miss." Dave was wearing a grin that not even Chad could miss, even though he could only see Dave out of the corner of his eye.

Chad pushed an elbow in Dave's stomach to finally get him off him. "No need for teasing!" Chad said, although he couldn't quite stop his own smile, even as Dave doubled over, acting like he was in great pain from the elbow, despite Chad knowing he hadn't done it that hard. "Oh, and stop that, I didn't hit you that hard!" Chad couldn't quite stop his voice from having a lift at the end like he was about to laugh.

Dave straightened up again. "But you're so teaseable," Dave pointed out, grinning.

"He is right on that!" Mark pointed out.

Chad turned back towards him. "Hey! What's that supposed to mean?!"

Dave just burst out in a full-bellied laugh at that. In some ways, Chad was also the perfect little brother to tease for everyone else.

But their goodhearted teasing momentarily stopped, as their goalie, Billy, who hadn't been involved, but was standing some ways away, said maybe a bit too loudly to another teammate, "You're coming to the gala on Saturday, right?"

A look of resignation crossed Dave's face, as he had never been a fan of the big fancy parties. On the other hand, the mention of the gala had started a thought in Chad’s head. Slowly, it unwound as his eyes widened, and a smile was etched into his features again. "That's it!" He said and grabbed Dave's shoulder.

"Oh, calm down there," Dave said. "What is it?"

"I can talk with him at the gala."

Dave looked at Chad and then blinked a few times before he sighed. "Of course you can." There was no stopping Chad when he had first gotten an idea in his head. "Just gotta make sure to pull him away from the other million people who want to talk with him as well."

Chad had a determined look in his eyes, "I believe I can."

Dave shook his head. "Of course you can, I don't doubt that," He said with a laugh.

"Who are you talking about?" It seemed like not everyone had started ignoring them just yet, as Mark was still on their case.

Chad shot Mark a small smile. "I'll tell you when it's a more sure thing," Chad said and grabbed his stuff, so he could start to leave.

Mark looked over at Dave, who just gave him a sheepish smile. "Can't snitch on my wife's little brother. She would kill me."

Mark snorted. "Right."

"I'm sure you will find out eventually," Dave said and grabbed his things as well, before shouting over the noise in the locker room. "Chad! Wait up," as he trotted over to him, so the two of them could walk out together.

"What's up?" Chad asked.

"You're coming by before the gala?" Dave asked.

Chad furrowed his brows.

"Diego has been asking about you, and I think I could use the backup. Besides, our house is closer."

"You just want me there in case she has another issue with the clothing, don’t you?" Chad asked, barely able to contain a laugh.

Dave looked sheepish. "She trusts you more on this than me."

"That's because you say she looks nice in whatever she wears!"

"Well, she does!"

Chad patted Dave on his back. "I'll be there. Maybe she won't know who to blame if we're both there."

"One can certainly hope," Dave said with a laugh, and they finally got out to the car park. "I'll see you then," He said, and with a final nod between the two of them, they parted ways. Dave went towards his car, and Chad towards his own. A car he had to get when his career took off, and it just wasn't plausible anymore to stick with the buses. He still didn't really enjoy driving if he was completely honest.

But he got into the car, threw his bag on the passenger seat, and then got out of the car park before going towards his home. The thoughts were still turning on the possibilities of how to even go about this, but nothing stopped the burning desire to finally want to do something about it.



It was with these feelings still going through him that Saturday slowly but surely approached.

He rang the doorbell at Diego and Dave's home, and a muffled "come in" sounded from inside the house, which prompted him to open the door and find his own way inside.

He found both Diego and Dave in the living room, as they had apparently decided to lay out Diego’s potential clothes here, rather than in the bedroom.

"Hi?" Chad said, trying to hide a bit of laughter, as he gently draped his own suit over one of the chairs that didn't have Diego's dresses spread out on.

"Perfect timing," Diego said, her hands on her hips, while she was wearing a floor-length navy dress that seemed a bit too tight, particularly around the stomach, where the baby bump was clearly showing. "I need someone with an actual opinion to tell me if I look good, since my husband cannot say anything other than I look nice." While her voice seemed a bit harsh, there was a warmth in that that never seemed to disappear.

"Hello to you too, sister," Chad said and went over and gave her half a hug, while Dave was mumbling in the background that it was because Diego did look nice.

Diego finally looked a little bit sheepish as they pulled out of the hug. "It's just that nothing fits like it used to."

Chad couldn't quite contain a little bit of a laugh. "I think that's your child's fault," with a not very hidden look down on the baby bump, which seemed to get bigger every time he saw it. "But I'm sure you have something here that will fit."

Diego huffed. "Everything seems wrong."

Chad gently nudged his shoulder against hers. "Come on. We have grown up with these kinds of parties. We know how to do it, and a little bit of a clothing issue has never stopped us before."

Diego sighed as her eyes glanced over the wardrobe that had been laid out in front of them. "Alright, we can do this."

"That's it," Chad said with a smile. He didn't particularly care for dresses, but since he had been the receiving end of Diego's clothing crisis on multiple occasions, he had at least, over the years, cared that his sister was looking her best.

Chad's eyes scanned over the clothes. "I'll go see if you missed any dresses, and then we will figure out what you can wear currently," He finally said, and with one last look over at Dave, who looked a bit less deflated now than he had earlier, he hurried over to where he knew Diego's closet was.

Most of the dresses had been pulled out, but still in the back he found a couple of options more, which he dragged with him into the living room, so he could lay them out next to the other dresses.

As he and Diego were going through the dresses and talking about which ones even had room for her belly, Dave snuck out in the kitchen, and came back out with some snacks for the three of them, which did make Diego give Dave a short, sweet kiss, before grabbing a piece of fruit, and continuing with their conversation.

Eventually, the two of them got settled on a moss green dress that Diego hadn't worn for years, claiming it didn't fit her right, but luckily, now it seemed like it would. While it still was a little tight around the belly, it wasn't annoyingly so, and still showed it off, which Diego had decided was a good thing.

Diego was lightly stroking her stomach, in a contemplative look, like she wanted to make sure it truly didn't bother her coming child. But even as she seemed distracted and Chad was trying to gather up the dresses that weren't gonna get used, so they didn't have to fill up every couch and chair, she still hit him completely out of the blue with a question.

"So why do you seem extra excited today? Did something good happen?" And then she looked up at him, with a knowing smirk on her lips.

Dave, who had been taking a bit of water to drink, was also about to spit it out at that moment, while Chad completely froze, a content smile frozen on his lips, as his eyes got a bit wider.

"Don't think I can't know when you're in a particular good mood... or are dragging my husband into some secret," She said, with that smug voice that Chad sometimes really despised. "So are you gonna tell your big sis or not?"

"Diego, it's really not anything," Dave tried to say, as he put back the glass of water on the table. "It's just a little.... something."

"A little something?" Diego raised her eyebrow.

"Yeah, you know...." Dave clearly didn't know exactly what kind of lie to give his wife, and luckily for him, Chad finally opened his own mouth.

"It's fine, Dave," Chad said, although he could feel his heart beating a bit faster, but still, he turned towards Diego, because while she was gonna tease him relentlessly, she also wasn't their parents. And she would know eventually anyway, if Chad was successful. "I'm finally planning on talking with Rex."

"Rex?" Diego asked, her eyebrows furrowed.

Dave butted in. "Rex Roofer. The guy who bought the team last year, and has basically reformed how we do things."

Diego had looked at Dave as he explained, but then sharply turned her head towards Chad. "Your boss?" Her voice was a little bit higher-pitched than normal.

Still, Chad just shrugged his shoulders and then let himself dump down on the couch where he had cleared a bit of space. "Yeah."

"And you're not worried about any.... I don't know, power dynamic that might fuck you over."

Chad blinked once, then twice, and then shook his head, grinning. "Nope!"

Diego crossed her arms and just looked at Chad, and then smiled. "Alright. If you're determined, who am I to get in your way? I gotta support my little brother's big dreams right?" she said and then went over to ruffle Chad's hair.

Chad let out a light laugh as the warmth and happiness filled him to the brim just sitting here with his family and feeling so accepted and supported, something he didn't think he would have just a few years prior.

"Thank you," He said finally.

"Any time," She said. "But if you're gonna romance your future beau, we gotta make sure you look your absolute best." She offered a hand to him. "So come on, get up, and let's get you all pretty for him."

"What?" Chad couldn't help but say.

Diego smirked. "Come on. I know you can make yourself pretty, but not pretty enough for this. Gotta give you that extra boost."

Chad was a little bit confused, but with one look over at Dave, who gave him a thumbs up while he was silently laughing, made Chad take his sister’s hand, who then pulled him up, and dragged him off to do something about how he looked, apparently.



While nothing drastic actually had happened, it was like the hair was sitting a little bit better, and the suit was sitting a bit tighter but not too tight on him, and he was not entirely sure how Diego had managed it, or if he was just imagining it.

But when the three of them were arriving in the giant hall, where the gala was taking place, he was feeling good about how he was looking.

He was walking alongside Dave, who had Diego on his arm, so the three of them could walk and talk. Diego was practically glowing, for despite her earlier dramatics, she knew how to work a crowd, and it was much more pleasant when she could decide what side of her she was allowed to show.

Dave seemed a bit more resigned to his fate, but was at the very least in a good mood as well.

Chad could feel his own energy almost vibrate in him, and while he did mindlessly grab an offered glass of champagne, his eyes were already searching for a certain someone in the crowd.

“What does he look like?” Diego asked, as she looked over at Chad, before looking around, but as she had never actually met Rex, she had no idea what she was looking for.

“Handsome,” Chad said, a little smile on his lips, just before he got hit on the arm by Diego, who had leaned in specifically to be able to hit him. “Hey!”

“That’s not a description!” She hissed at him.

“He is probably gonna be the most fancy dressed around here,” Dave pointed out. “Tall, short black hair. Looks like he is planning something most of the time. Oh, and look, there he is.” Dave hadn’t even gotten through his sentence before he spotted him and pointed him out to Diego.

Rex was standing off to the side, talking with a woman, who was laughing softly at something he was saying, while he seemed to be smirking slightly at her. They seemed completely at ease with each other in a way that Chad was sure he hadn’t seen Rex before.

“And who is that with her?” Diego asked, pulling Chad out of his thoughts once again.

Dave shrugged, while Chad said, “I don’t know.”

“She certainly is not someone who has shown up at the club with him,” Dave added, although he still looked like he was thinking.

“Well, there is no time like the present to find out,” Diego said with a shrug, and then circled over to Chad. “And I’m sure you did promise me to introduce me to the new owner, that you have spoken so much about,” she said, and then just started dragging Chad towards Rex and the beautiful woman.

Chad could feel his heart in his throat as he was walking over there, but as soon as they approached, Rex and the woman seemed to stop their conversation and looked towards them. Which was apparently what prompted him to finally straighten his back and walk with confidence towards them. If you didn’t have the confidence, then you better had to fake it, something he had been taught from a very young age.

“Hello,” Chad said, his eyes on Rex, and he could feel some of the confidence already faltering. He hadn’t actually spoken with Rex face-to-face like this before. The only time had been that brief meeting last year. “I’m Ch…”

“Chad Sterling,” Rex offered with a smile, as Chad had seemed to falter in his own sentence. “My star player. It’s hard to miss you, both out on the field and in here.”

Chad could feel Diego’s finger digging a bit more into his arm, no doubt in excitement for him.

“Y-yeah,” Chad said, and tried to clear his voice. “Thank you for inviting us.”

“I’m glad you could make it.” Rex’s eyes seemed to finally drift towards Diego, who had been standing next to him.

“Ah!” Chad exclaimed as he noticed and looked over at Diego, who had… a bit of an unreadable look on her face, which was never a good thing for him. “This is my sister, Diego Dodgers. She is married to Dave on the team,” he said, and cast a brief glance back towards Dave, who seemed to be much happier talking with some of their teammates.

“It’s a pleasure to meet you,” Rex said, and took her hand in a firm handshake.

But then a clearing of throat forced all three of them to finally look towards the woman who had been standing next to him. Her eyes were dark and sharp, and there was an air of elegance around her, although Chad was sure there was a glint of smugness in the way she held herself.

“My apologies,” Rex said. “This is Camille Roofer,” he said, and while he certainly did not elaborate on her exact position, the way her hand curled around Rex’s arm left plenty to the imagination. Especially as Chad was perfectly aware that Rex did not have any siblings.