/Sorry this took a little longer than others. I'm on vacation with family atm. But nevertheless, here you go! I hope you enjoy. These cuties makes me squeal. Review please? Tell me what you think! Thanks, darlings!
"DEAN! Are you ready to go yet?" Sam called through his open bedroom door. It was 5:00pm and Sam promised that the car would be outside Jessica's door no later than 6:30. When the boys got back from the diner around one in the afternoon, his date took priority over everything else on his mind. Well, except for a miniscule, little weight in his gut that he couldn't shake. But he didn't have time to deal with that right now.
Dean let it slip to Bobby that Sam was going on his first date and he was so excited that he personally reserved a table at his favorite restaurant.
"It's one of the nicer ones, not some old, dingy, twenty year old Denny's. The manager owes me a favor anyways. It'll be perfect," Bobby said over the phone. Sam reluctantly agreed and tried to comfort his mind by telling himself the restaurant will be fine. She'll like it. He hoped.
He tried relaxing with a book while he still had a few hours to kill, but his mind kept constructing every possible way the evening could go horribly wrong. What if he knocked on her door and her dad saw him and didn't let her go? What if he clumsily spilled food on himself at the restaurant? What if.. The list went on endlessly. By the time Sam had to start getting ready, his hands were starting to tremble.
Sam probably could have waited two more hours to get ready and they would still have time to spare, but he wanted to make sure. There is no way he's making Jessica wait. The getting ready process was all done with nerves getting more intense every time he looked at the clock. Shower, blow drying hair, clean and unstained dark pants matched with a light blue buttoned plaid shirt. He even sneaked in a little bit of Dean's cologne when he wasn't watching.
Dean met Sam in the kitchen and motioned to the digital numbers displaying 5:17 on the microwave, "Sam. Will you chill out? We have plenty of time. It only takes fifteen minutes to get to Jessica's and then-"
"Fifteen minutes to Jess' house, then another fifteen to the restaurant. That's assuming we take the freeway. I checked this morning," Sam interrupted, his mouth moving at a hundred miles an hour.
"Yeah, and you checked last night too. And I saw you look it up on your phone on our way home. Sam, you need a beer or something." Dean said lightheartedly, but just received a cold glare in return.
"Shut up, Dean," was all the little brother could muster up. He was fidgeting with his fingers on the kitchen counter like he always does when he's nervous.
Dean's big brother instincts told him that this was when he was supposed to step in with some reassuring words. So he rounded the island and gently pulled Sam off the stool.
"Alright, come here. Let me get a look at you," said Dean as he brushes off the blue, plaid shoulders. "Sam. Your hair. It makes you look like one of those private school prep boys that where sweaters like capes," the older one criticized. His hand instantly went to offer Sam's hair some assistance. After some expected resistance, the shaggy hair was tousled and shaken to Dean's liking. "There. Makes you look a little daring I'd say. Jessica won't be able to resist you." Dean looked at his brother the same way an artist looks at his finished masterpiece.
"I hope you're magic hair trick works on her parents too," Sam groaned as he smoothed down his shirt.
Parents. This was not one of Dean's areas of expertise. He dodged that bullet with Cas, but is still dreading the first holiday that all his older brothers will return for a family reunion. But for Sam, he'll attempt any kind of help he can give. "I don't think you'll have a problem with that. You're smart, got good grades, you're polite, you're what parents want for their daughter. So don't sweat it."
Dean felt accomplished when the kid finally was able to crack a smile. It was all true. Sam didn't have a rotten bone in his body. Dean couldn't help but wish he was as good as Sam was. The idea that Sam was the one who worshipped him blew his mind, because Dean believed Sam was already so much better than he could be.
"Uhm, Dean? I don't mean to be rude but.. are you planning on changing before we leave?" Sam asked with a raised eyebrow.
Dean inspected his ACDC shirt with a small hole at the edge of the left sleeve and his faded jeans with an oil droplet trail on his knee. "What? You're the one with the date, not me."
Sam groaned and rolled his eyes. "Please Dean? Just no rips or stains. Jess is still gonna meet you when she gets in the car and.. look I really like her and I just want.. C'mon Dean, do it for me?" Sam pleaded. He saved that line for the extra important things he needed Dean to do.
Dean lets out an exaggerated sigh and trudges to his room. "Fine. But don't push it Sammy. Or you and your girlfriend are taking a hike back home after dinner," Dean threatened as he pulled out a new shirt and a clean pair of dark jeans.
"No you won't!" called Sam from the kitchen. "I heard Bobby make you promise to drop off and pick us up and not a minute late."
Dean could almost hear his brother smirk. In his opinion, Sam straddles the line between just plain smart and a smart ass. Dean emerges from his room in a dark, solid blue v-neck and black jeans. He does a three sixty for Sam to approve.
"Good now? No stains or rips except for one tiny hole in the crotch. But I don't think Jess will be looking there so I think we're good."
The brothers killed a few more minutes with light hearted jokes and stories of Dean's first "date" which was basically a make out session behind the bleachers with hot cheerleader Anna Milton freshman year. Finally, Sam saw the microwave flash the time 6:05 and Sam jumps to his feet.
"Dean! We gotta go. I don't wanna be late because of traffic," Sam exclaims as he grabs his jacket and opens the front door.
Dean grabs his jacket and the keys and strides out the door and Sam follows nervously but excitedly follows and shuts the door behind him.
The clock in the impala read 6:15 and they were five minutes away from Jess' house. The car has been mostly quiet except for Sam giving directions to which Dean always replied "I know, Sam. I Googled it last night." Sam was rehearsing what he would say when the door opened and he was in front of Jessica's parents. He tried to make Dean believe he was totally cool, but Dean could sense his brother's nerves radiating from the passenger side.
Dean fished in the middle compartment for a small metal tin. "Here, Sammy," he offered. Sam opened the box to find small white tablets. "They're lucky. Go ahead and take one." Dean noticed his brother's wide, apprehensive eyes. "They're breath mints, Sammy!" The look didn't change. "They're clean. Promise. Just take one."
Sam popped one of the tablets into his mouth and tasted the minty flavor making his mouth cold. "Lucky, you say?"
"They haven't let me down yet. Just ask Cas. He loves them."
"Dean, Cas would love you even if your breath smelled like pickle juice and onions." Both of the brothers laughed.
"Shut up," Dean said while chuckling. "So you ready?" They pulled up in front of the address Sam's practically memorized by now and slowed to a stop.
It's 6:27. Sam stared at the dark green front door for at least half a minute without saying a word. He swallows the lump that has built up in his throat and tries to even out his breathing. "Dean?" Sam's voice was small, "I'm still nervous.."
Dean put a comforting hand on his brother's shoulder. "You'll do great. Just be the brilliant Sam Winchester that we all know and love."
Sam cracked a smile and let out a long breath. Okay, it's time to do this. Don't want to keep Jessica waiting. He exited the car and started up the gravel pathway. That lump in his throat started to form again. He rang the doorbell and fiddled with his fingers while waiting for someone to open the door.
A middle aged man with round glasses and a collared shirt came to the door. Sam grabbed a quick breath and spoke clearly and firmly, trying to sound as confident as he could, "Mr. Moore? Good evening, I'm Sam Winchester."
The man inspected Sam in the doorway, from the tips of his hair to his faded shoes. Then he smiled and Sam felt he could breathe again. "Ah. Evening, Sam. Jessica's been telling us about you. Why don't you come in and relax. Honey!" he called to his wife, "Sam's here. Come say hello."
Sam walked into the clean living room and took a seat on a brown, leather couch after introducing himself to Mrs. Moore.
"Jess! Sam's here!" The woman with blonde hair called upstairs. "Sorry to keep you waiting. That girl has tried on at least six different outfits before you got here." This made Sam smile.
"Mom!" Jessica's voice from upstairs was irritated and a little embarrassed.
Sam chuckled and said coolly, "I don't mind waiting. You have a lovely house." The mother thanked him for the compliment. Sam was doing great. This wasn't as bad as he expected. He was actually good at talking to parents. For the next few minutes Mr. and Mrs. Moore asked Sam about school, hobbies, et cetera. Mr. Moore's ears perked up when Sam mentioned his interest in becoming a lawyer.
"Law, huh? That's a great field. I know it's still a long ways away, but have you considered any specific colleges?" The man asked in a kind and easy going tone.
"Well, my brother, Dean, says I should apply to Stanford. But I'm not sure if they'll accept me. They're standards are pretty high." Sam said modestly. Another little trait that Sam subconsciously inherited from his older brother.
"What, intelligent, hardworking boy like you? I think you should go for it. Maybe you'll rub some of that off on Jess," the dad teased.
"Very funny, Dad." Jessica was half way down the stairs wearing a pair of denim jeans, blue blouse with ruffles at the bottom, and wedged heels about one and a half inches tall. Her long, golden hair was curled and there was a touch of sparkly lip gloss on her lips. She entered the living room and smiled when she saw Sam. "What, too casual?"
Sam's attention was enthralled by the sight of Jessica coming down the stairs. It took him a second to process the question. "No, not at all. It looks," he cleared his throat, "you look nice."
The two smiled and Sam started towards the door. "We better get going. Our reservations are in fifteen minutes," Sam said still looking at Jess.
"Where you kids eating?" Asked Jessica's mother.
"Harvelle's Roadhouse. It's my uncle's favorite restaurant and he's friends with the owner," Sam informed. He then held the front door open for his date and walked onto the front porch. He turned back to the parents who were now standing in the doorway. "Thank you for letting Jessica go out tonight, Mr. and Mrs. Moore. We will be back to drop her off tonight."
"Jess, no later than ten, understood?" Mr. Moore informed his daughter.
"Yes, daddy," Jessica replied. Sam thought her voice sounded like wind chimes.
Mr. Moore then caught sight of the impala waiting in front of the house. "That your brother?" Sam nodded. "Nice car. Tell him to drive safely."
"I will, Sir. You don't have to worry, my brother won't let anything happen to us," Sam said with admiration in his voice. It was true. He didn't feel safer anywhere but with Dean.
Jessica kissed her parents on the cheek and waved one final goodbye before walking next to Sam, who opened her door for her before going around to the other side to let himself in.
Dean smiled as he looked at the kids in the rearview mirror. "You guys coordinate your first date outfits over the phone or something?"
Sam and Jess looked from their own shirt to the other and just started laughing.
"Apparently we did," laughed Jessica.
"By the way, I'm Dean. Sam's older brother. You don't have to introduce yourself. You're the famous Jessica Moore." Dean put on one of his half smiles.
"Dean!" Sam's voice was one of disbelief.
Jessica just smiled at the boy sitting next to her. "Nice to finally meet you, Dean. Sam talks a lot about you. And famous? Hope Sam hasn't told you anything too bad."
"No nothing too bad. He just told me about you stole a car a few years back and ran from the cops." Dean laughed to ensure the girl that he was kidding, but evidently he didn't have to.
"Dammit Sam! I told you those records were expunged!" Jessica played along with Dean's joke and made the two Winchesters laugh at her quick response.
"I like her, Sammy," Dean said looking in the mirror at the back row.
The younger brother looked from Dean to Jessica. "Same here, Dean." Jessica smiled and blushed a little. Dean gave his brother a 'smooth move' look in the mirror.
The impala pulled up to the roadhouse and slowed to a stop in front of the entrance.
"Alright, you kids have fun. Just send me a text and I'll come get you guys. And anything from the bar is off limits, Sammy," Dean commented.
"Right, Dean. Because that's totally something I would do," Sam retorted sarcastically. "Okay, I'll text you. See ya later!" And with that, the impala revved and left the excited and nervous fourteen year olds at the restaurant.
"Reservation for Winchester?" Sam said when he got to the front desk. A slight smirk grew on his face, thinking he sounded very mature for having a reservation. Jo recognized Sam as soon as he walked through the door and easily picked up on his trying-to-be-cool tone.
"Ah yes. Mr. Winchester. Table for two. Will you be needing any kid's menus?" Jo asked playfully trying to embarrass the little boy, who she's known since he was in diapers, on his first date.
"Jo!" Sam complained. "Jess, I swear not all of my family and family-friends are like this." Sam looked back at his date as Jo led them to their booth by a window.
"I think they're great, Sam. Hilarious, I might add. You're the only one not laughing," Jessica said with a sincere smile as they sat down on the leather padded seats.
Jo let out an amused giggle as she set down menus. "I like you, Jess. We could be great friends. You fit right in with Sam's crowd."
Dinner started out without Sam embarrassing himself any further than Dean and Jo already have. The two ordered a couple burgers and soda with a plate of fries in the middle to share. Sam thought everything was going well. They talked about anything that came to mind. School, movies, embarrassing stories about Sam's family members, and much more. The conversation was effortless and natural. All the nervous jitters melted away and the two teens just enjoyed each other's company.
Everything was perfect.. Until Sam's long arm knocked over his sprite. Shit shit shit.. The clear liquid started running off the other end of the table and threatened to land on Jessica's jeans. She quickly dodged towards the inner part of the booth and let the soda drip onto the spot she was formerly sitting.
"I'm so so sorry," Sam started with a flustered tone. He grabbed a couple napkins and started wiping up his spilled drink on the tabletop and then walked around to clean the seat.
Jessica watched Sam frantically clean up the mess as he repeatedly apologized. She didn't respond until he sat back down in his seat looking a couple shades of red. "It's okay, Sam. I'm fine, see? Not a drop." Sam started to relax at the sight of Jessica's smile. She reached for a few fries and after putting one in her mouth she threw the other and it bounced off Sam's cheek.
"Hey!" Sam said in surprise at the airborne fry.
"That's for almost making it look I peed my pants," Jessica said jokingly upset.
Sam smiled wide and stared at her for a few seconds before deciding to grab a fry to retaliate. Jessica gasped as it landed in her hair and the two of them started to break out into laughter. A few more shots were fired before Jo walked by and gave their table a stink eye. And they bit their lip to suppress their remaining giggles.
When the kids were finally able to catch their breath, Jessica put an elbow on the table and rested her chin on her palm looking across the table curiously. "So, tell me Sam, if I ask you something will you answer completely honestly?"
"Yeah, of course. What is it?"
"When you first saw me in geometry what was your first impression. And I want honest. Don't just be nice to make me feel good." She stared at Sam's face as his mind went back to the beginning of the school year.
Sam remembered the first week of school and always staring at the clock for his last class to finish. Jessica sat in the row to his right and four seats in front of him. He noticed her long, blonde hair from day one. It reminded him of the picture he had of his mom in his wallet. Sam really started to notice her when she would raise her hand with the right answers every time. She impressed him. Brilliant really. So brilliant and beautiful that he had never thought a girl like Jessica Moore would notice the kid with matted hair in the back row.
"It probably took about a week for me to know I had a crush on you. By then I knew you were pretty, smart, funny, and more. But..," he stirred the remaining ice in his glass with his straw as he hesitated, "but I honestly never would have really done anything about it. I was so surprised when you called me over at the end of class yesterday." His looked innocent and vulnerable for a few seconds. He finally met Jessica's eyes to see her expression.
Jessica had a surprised look on her face, "a week? Why didn't you say anything?" She said it as if it was as easy as asking someone to pick up your pencil.
"Well," he broke eye contact once again, "I have to answer honestly right?" Jess nodded. "Well I just never thought you would have even looked in my direction," Sam admitted sheepishly. "I mean, look at you! You're Jessica Moore. Who doesn't adore you?"
Jessica blushed but quickly rebounded. "Yeah and you're Sam Winchester! What makes you think I wouldn't have noticed you?"
"If you haven't noticed, I'm not exactly the coolest guy around campus.." His voice let the sentence hang. Not like Dean Sam's thoughts finished.
"Well I think you're pretty great, Sam. You're smart, funny, you were a hit with my parents, and that's highly impressive, you drive around with your brother in his cool car, Sam to me you're pretty brilliant," Jessica said in awe. She bit her lip, a little nervous. She wondered if she sounded like a complete idiot. Sam just smiled at her and prayed he wasn't blushing too noticeably.
"Thanks Jess." The two smiled at each other.
The rest of their date followed the same course. They discovered trivial things about each other. Favorite colors, pet peeves, childhood stories, and the list went on. They talked endlessly until most of the other dinner customers have gone, save for a few bar hoppers. They didn't even notice the surrounding booths starting to be wiped down for the night.
Sam looked down at his wrist watch and gasped at the time. It was 9:15. Neither of them would have thought they've spent over two whole hours talking about nothing and everything. "Woah, it's late. Jess, you gotta get home soon. I'd like to stay on your dad's good side for as long as I can," said Sam said with a grin. But he knew that he had to give Dean fifteen minutes leeway to get to the roadhouse.
"Ugh. You're right, unfortunately." She sounded sincerely displeased that they didn't have more time together.
Sam paid for dinner and then took out his phone to text Dean.
Hey Dean. We lost track of time. Could you come get us? Jess has to be back by 10.
The two of them then decided to sit on a bench out in front of the restaurant under the night sky. Sam wrapped his jacket around Jess and they sat there for a few minutes hand in hand. Although Sam wouldn't have minded that moment to last for hours, he was worried that he wouldn't get Jessica home in time. He nervously checked his phone for Dean's reply.
No New Messages
Sam tried again in five minutes.
Dean? Did you get my last message? I really don't want Jess to be late. We're out front. Text me back.
Sam continued to check the phone but saw the same disappointing empty inbox every time. He started to worry. Dean always replied to Sam's text messages. Why would Dean not have his phone on him?
Two more messages were sent in the next fifteen minutes.
Dean. Where are you?
Seriously Dean. Did something happen? What's going on?
They sat out on the bench for a good thirty minutes before Sam felt a vibration in his pocket. It was now 9:35.
Be there in 5.
Sam stared at the short message in confusion. His brother was never late picking him up at anything for as long as he could remember. He tried to relax for Jessica's sake but he couldn't shake the thought of what could Dean be too busy with to not check his phone? The answer wasn't prominent in Sam's mind but on some level of his subconscious he knew exactly where his brother was and what he was doing.
/ Next chapter we'll figure out exactly where Dean went after dropping his brother and date off and if Jess gets home in time. But let's hope so for Sammy's sake. Thanks for reading! Again, tell me what you thought. I love hearing your guys' opinions.