(Narrator POV)
Graduation for Jo, Sam, Meg, and Jess was swiftly approaching as late-spring came the year after Dean and Castiel got Jack.
Both men were now 26 while Claire was 2 and Jack was 1 (birthday in May) so that meant that all the soon to be graduates were 22 (except Jo and Meg. Jo was 21 because she graduated high school early, and Meg had declared it rude to ask a demon's age).
Charlie hadn't been able to find a place that made both her and Jo liked, so they decided to wait to move in together. In the meantime, Jo was going to move back in with Ellen in the apartment above the roadhouse (Ash still lived in, and rarely left the back room), and Charlie was going to live with Cas and Dean for a few months.
Benny moved out of the apartment with Pam, and went to live in the apartment above Devil Horns and Angel Wings. Gabe moved in with Pam in the apartment above her store, after getting rid of his own apartment.
Sam and Jess picked out an apartment to stay in until they could afford a house, and Meg was going to stay with them for awhile.
Rowena and Crowley both had their own mansions (that nobody knew the locations of).
Charlie had started up working for Cas at the flower shop and the market, while Jo resumed her work at the Roadhouse. Meg started working at Dean's bar with Benny, while Sam and Jess had both gotten internships.
Sam had been accepted into a nearby law school and was interning at a law firm called 'Thomas and Yard'. Jess got into a medical school not far from him, and was interning at Sioux Falls General.
It was another segment of busy time for the family, and nobody was too surprised when Sam and Jess wanted to add even more events to their schedule.
A wedding was on the horizon.
(Time Skip)
Dean entered the room Sam was in to find his little brother pacing back and forth.
"You keep pacin' like that, you'll wear a hole in the carpet." Dean paused when Sam froze in his steps. "At least, that's what Mom told me on my wedding day when I was trying to turn pacing into a sport."
Sammy sighed and flopped onto the white couch in the, otherwise sparse, room. "You were nervous too?"
"'Course I was nervous, I was about to take the second biggest leap of my life." Dean said and then elaborated at Sam's confused face. "Dude, kids are way scarier than marriage, in my experience."
"Yeah, I guess I understand that." Sam admitted, but still looked worried.
"Do you love Jess?"
"Well, yeah, obviously."
"Then why are you stressin'?"
Sam took a moment to think over his answer and then took a deep breath which turned into a sigh.
"I've been having these dreams." He started, but didn't get to the next part.
"Oh, boy."
"What?" The younger asked with a slightly offended tone of voice as he looked over at his brother.
"Nothing. It's just that you overthink everything, man. I'm amazed you haven't given yourself an ulcer yet." Dean explained before waving his hand in a 'go on' gesture.
"Whatever, man. I've been having these dreams, and in them Jess dies just like mom did. Fire, ceiling, the whole thing. It's duplicated almost exactly to what happened to Mom."
Dean wasn't really sure how to respond to that. It freaked him out, and he didn't want to say the wrong thing while he was trying to calm himself. Finally, he replied.
"They're probably just stress-induced. You're nervous about the wedding, and so your brain is takin' the story you heard about Mom and turning it into a nightmare about Jess."
"See, I would think that too, except that I have no memory of what happened to Mom. You and John never told me, and I was a baby when it happened." Sam said back.
Dean kind of hated that that was true. John wouldn't talk about Mary at all, and so he obviously never spoke about how she died except that something killed her and he'd kill it when he found it. Dean only shared the happy things about their mom with Sam, wanting him to remember her in a way that wasn't as tainted as Dean's own memories.
He would always love his mom, but sometimes when he thought about her singing 'Hey Jude' to him or making him apple pie, flashes of fire would cross his mind. Dean hated that all the memory snapshots of Mary were singed around the edges.
The last thing he had wanted was for his little brother to experience the same.
"I only know that my dream is what happened to Mom because I asked Dad to tell me what John had told him." Sam finished, referring to Bobby and how the old hunter seemed to know all the Winchester tales despite not actually being one.
Again, Dean was sort of at a loss for words. He wasn't sure how to make Sam feel better in the face of such frightening dreams.
"Sam, don't worry about it, alright? What happened to Mom, isn't gonna happen to Jess. You know why?" Sam shook his head. "It's not gonna happen because Jess has both of us ready and waiting, in case Mom's killer comes back. We already know about him and the supernatural, there's no way he'll get to strike again."
"You're certain?"
"I'm your big brother, Sammy, and I swore to protect you. I always have protected you and I always will, right?"Sam nodded. "Well, that protection translates onto Jess, and any little gremlins you two have, okay? Nothing will happen, cause ya got me."
The younger of the two may have been 22 and a college graduate that was about to get married and become a lawyer, but he still had at least one thing in common with 8-year-old-Sammy.
An undying faith in his big brother.
There wasn't a lot that Sam remembered about their childhood before Bobby, but he could recall that Dean always took care of and protected him. Dean would have laid his life down and died for Sam, or killed for him in the same breath. He was devoted to protecting his baby brother and that had never changed, even after they left John.
Sam knew that it may be childish to think that your older brother can do anything and solve any problem, but he honestly had no evidence to the contrary. Dean had always seemed invincible and done things that nobody else could do.
He was a gifted hunter, a fierce protector, an amazing brother, a great father or father figure, and a genius in his own right. There had never been anything that Sam didn't think Dean could do.
So, it may seem silly to think that your brother can be the sole protection between your soon-to-be-wife and the supernatural that took your mother, but Sam was confident in that thought.
He was still worried and stressed, but knowing that Dean had his back made it ten times less scary.
"Okay."
With that bit handled and a grin on his little bro's once anxious face, Dean stood with a flourish and yanked Sam up too.
"Okie-dokie, kiddo! Time to get you out of these sweats and into that suit, you've got a ball-n-chain waiting!"
Sam laughed and went into the bathroom to do as he was told.
(Time Skip)
At the altar, Sam awaited his beloved while wearing a black suit, white dress shirt, and black dress shoes and tie.
They were in a park that had many trees throughout, and a small river running through it. The river was behind the altar and the trees above were filled with fairy lights.
Brown chairs were on either side of the white aisle, and Jess's family (which she wasn't very close to) was on the right while Sam's family was on the left.
The different sides were quite jarring, since everyone on her side looked virtually the same (blonde, blue eyes, fair skin, generally attractive) and everyone on his looked quite different (mixed in most categories, still mostly attractive though).
Most of her side was also dressed fairly blandly while Sam's family was wearing a wide array of colors (Meg in dark red, Ash in a bright yellow suit, Rowena in a silver gown, Gabe wearing lime green and black, Dean in dark grey and black, Castiel dressed in yellow and black, Claire in a tiny outfit of yellow, Jack in a tiny grey suit, and so on).
It was kind of a mystery how Jess came from such dull creatures.
The music started on the harp which announced Jess's entrance and she made her way down the aisle
She had on a beautiful white wedding dress with a long train and spaghetti-strap sleeves. The neckline was straight across, and when she walked it was shown that her long skirt was hiding white converse.
The dress was a pristine white with a layer of small sparkles over the skirt and train. Those jewels were less frequent at the top of the dress and around the waist.
A diamond necklace was around her neck and she had a friendship bracelet on her right wrist (it was a worn brown string with a single blue-green tie-dye bead. Sam had a matching one.).
Her curly hair was pulled into an updo that still showed off the curls and let some hang down at the front to frame her face.
Sam was in tears when she made it up to him at the altar, and he took her hands the second she joined him.
The minister droned on for a bit before he finally got to the vows and told Sam to go first.
"Jess, the second I saw you, I fell in love. I never really believed in love at first sight, until I caught a glimpse of you on campus. I remember calling my brother and telling him that I had met the most perfect girl, and I was right. You're the most amazing woman I've ever met, and you're more perfect than anyone I will ever meet in the future. There's no way to tell you how deeply my love runs, so I hope you can be content knowing that I will try my best to show you everyday for the rest of our lives."
Sniffs were heard throughout Sam's side and Jess had tears in her eyes.
"Sam, you are the best person in my life, and you have been ever since I met you. I knew from the moment we met that we would be together and I remember thinking that there was no way I wasn't marrying you. You were always the one person I knew I could trust with anything and I have loved you since that first coffee date. Not only have you loved me more than I ever thought possible, but you also gave me a group of people who accept me for me. You have shown me love and care from the moment we met, and I hope that you'll let me do the same until the end of time."
Sam was crying now too, and the others in the audience weren't much better.
"Do you Sam Winchester-Singer, take Jessica to be your lawfully wedded wife, to have and to hold, to love and to cherish, in sickness and in health, for richer or poorer, til death do you part and as long as you both shall live?" The minister asked Sam.
"I do." The ring was put on.
"Do you Jessica Moore, take Sam to be your lawfully wedded husband, to have and to hold, to love and to cherish, in sickness and in health, for richer or poorer, til death do you part and as long as you both shall live?" He asked to Jess.
"I do." She said instantly, and the other ring was slid into place.
They were announced husband and wife, and immediately jumped into the kiss.
Applause rang out as they pulled away and made it back down the aisle toward where the reception would be held.
(Time Skip)
There was a wooden dance floor set up in part of the park for the dancing portion of the evening, and so the couples quickly took their chance.
After many songs with the newlyweds dancing together, Jody abducted Sam and Bobby swiped Jess so each could have a dance with their happy children.
A couple more songs later, Castiel went to give Ellen a break from watching Claire and Jack so she could dance too while Dean spoke to Jess.
"Hey, can I cut in here?" Dean asked as he tapped Bobby on the shoulder.
"Sure thing, but I'll be back." He warned with a smile to his son and now official daughter (in law). A wink was sent her way, making her laugh, before he wandered off to go find his wife.
Jess beamed at Dean as Bobby passed her hand off to him and they started dancing together on the floor.
"So, how's the married life, sister dearest?" He asked with a cheeky grin.
"Pretty good so far. How's it been to you, brother dearest?" She grinned back.
"Amazing." Was his instant reply.
Jess and Dean may not have spent too much time together in person since she and Sam had been in California for majority of their relationship, but the two still liked each other.
Between the obligatory family get-togethers and calls, and the things they heard about each other through Sam, it was almost like they had known each other for forever.
Unlike her boring family that was brooding in the corner.
"God, I can't believe my family is here. They're insufferable." Jess said with a sigh as she stared over at them.
"Why'd you invite them?" Dean couldn't help but ask as he glanced over too, before returning his gaze to her.
Jess kept staring over at them while she seemed to truly contemplate why she had invited her awful relatives to the happiest day of her life (so far).
When she spoke again, it was very quietly and in the saddest tone Dean had ever heard from the normally happy and fierce woman his brother loved.
"Because I want to love them."
Jess seemed to realize what she said and tried to lighten the mood a bit, knowing that Dean was not a fan of the serious and somber.
"They always compare me to my sister, little Miss Perfect. If I didn't invite them, they'd never stop talking about how Victoria invited them to her destination wedding in freakin' Hawaii. In my defense, I didn't think they'd actually come."
She hadn't really lightened anything, but at least she gave it a shot. Still, she felt safe enough with Dean to add one more thing on.
"I wish they weren't my family sometimes."
It was an admission she'd only ever told Sam and Meg before, but Dean was different. Everyone in the family knew that Dean was different. None of them (except Bobby and Cas) really knew exactly what happened before they became Winchester-Singers, but they knew enough.
Dean had done everything he possibly could to protect Sam, and when he couldn't shield Sam any longer in that environment, he took Sam and ran.
Sam didn't remember much of that night, but he had told Jess that he remembered just enough to know that Dean had saved his life.
The fire of protection that raged in Dean was soon spread all across the family, and he became a sort of guardian in a way.
Not that he knew any of that.
"They don't have to be." Dean speaking again broke her out of her thoughts and she had to retrace their conversation to get back to what he was talking about.
Right, how she wished they weren't her family sometimes.
"What do you mean?" She couldn't help but inquire.
"I mean that if they don't treat you the way you deserve, then you shouldn't try and tolerate them as much as you do. If you want them around that's fine, but you shouldn't see them if you don't want to."
"They're my family." She offered weakly, not really buying into it.
"So are we."
Her gaze snapped up to meet his eyes from where she had been looking at his shoulder in thought.
"What?" Jess asked very quietly, in awe.
Sure, Sam had called her family, but having it confirmed brought tears to her eyes.
"You've been family ever since Sam called to announce that he was in love with you. You've been part of the family for years now. Today just made it legally official." Dean told her simply and gave her a grin.
Jess had to take a deep breath to avoid crying, but she still looked to the other Moores with conflicting thoughts.
"Dad once told me that 'family don't end in blood', but it doesn't start there either. Family isn't the people you're related to, it's the people you relate to. Family is the the group of people in the world that love and understand you, the ones you want to spend all of your time with." He told her like it was the most simple thing in the world.
She supposed that maybe it was that simple.
"Family is anyone that's there for you when a family should be."
Jess looked back up into his eyes again and she knew that he was right.
Her biological family had never been there for her unless they needed something. They didn't care about her achievements, they just liked to use her as a comparison to her sisters. They always ridiculed her and made her feel like she was a disappointment.
Nobody in the ragtag little family of Singers, Harvelles, Winchester-Singers, and more ever made her feel like that.
"I don't have a drop of Singer blood runnin' through my veins, but that doesn't mean that Bobby isn't my dad. He is, and just because you don't share blood with any of us either, doesn't mean you ain't family." Dean said solemnly, clearly thinking about some darker times of his own.
Jess had tears in her eyes as she hugged him suddenly. He made a noise of surprise, but hugged back.
"Man, you don't get sentimental often, but when you do, you really go for the gold, huh?"
"It's all a part of my dazzling charm." He replied instantly and without a hint of his previous sadness.
She laughed and he grinned as they both pulled back from the hug.
"Now, no more chick-flick moments! You got a line of family waitin' to dance with you." Dean announced and took a step back.
Jess looked over her shoulder and laughed at the sight of all the different non-bio family members (not just the men, either) waiting in a line to dance with the bride.
Yeah, this was her real family for sure.
She turned back to Dean and the two shared a big grin. "Thank you"
"Anytime, sis."
Jess stepped up to give him a quick kiss on the cheek before going off to dance with the large group waiting.
Dean laughed as an argument broke out over who'd get to dance first, Gabe or Charlie.
His money was on the Queen of Moons.
"Hope you aren't trying to steal my wife." Sam said as he stepped over to his older brother. He was smiling big, somehow knowing exactly what his two favorite people had been talking about.
"Nah, I'm pretty happy with Cas." Dean replied with a chuckle and gave his husband and their babies a little wave.
He was about to head over to them, but decided to splash some water on his face first. With a 'see ya later' and a quick hug to his brother, Dean headed off to find the bathroom.
The hunter just wanted a minute alone after the speech he gave to Jess. He was glad that he cheered her up, but he had brought up some of his own memories of old doubt.
It wasn't too bad though, so a few minutes and some splashed water should solve the problem. Then he'd get back to the party and hang out with Cas and co. (Jack and Claire).
The small building in the park for the bathrooms wasn't far, so he got there pretty quickly and went around the corner to find the door.
Only to find Benny and Meg obviously flirting by the wall.
"Oh god, why is it always me that finds the couples!?" He exclaimed in exasperation. "Since when are you two even a thing?!"
Dean paused as he realized something. He looked at the shameless couple standing by the building, in utter disappointment.
"Seriously? Flirting at a wedding? What is this, a rom-com?"
A/N Hello, all! This chapter is so long so congrats on finishing it. (Editing-Author here, I am currently going through the story, and I'm upset with myself for making these chapters so long.)
Jess is mostly an OC because she's not in the show very much, but I always imagined that she'd get along surprisingly well with Dean once he quit flirting with her.
I made Jess's family bad because I feel like most of them have very little or very bad biological family, so it'd make sense if she were the same way.
Also, I always love close families in shows, but I especially love when they aren't blood-related to one another. Family really doesn't end in blood, or always start there either.
Enjoy and keep reading!