After their night of celebration in honor of Klaus' demise and Katherine's entombment, Sam and Dean decided to stay at the boarding house for a little bit longer instead of returning to Rufus' cabin in Whitefish, Montana. During their stay, not only did everyone tie off any loose ends when it came to Klaus (mainly sealing up and spelling Elijah's daggered body) but both Sam and Dean had their turn in getting to know Elena, in their own way, and everyone she cared about but most of the bonding happened between the newly reunited father and daughter.
Although for the Winchesters, bonding with Elena wasn't that simple due to the remaining adults that she had in her life; Jenna and John. The mess that John had created by calling in Isobel had to be resolved when it came to Jenna so with the help of Sam and Damon, Dean took it upon himself to help not only Elena but Alaric as well when it came to mending the broken dynamic that John had set into motion.
The only way to do that was to tell the truth...the whole truth.
No one liked that idea but Dean didn't care; he saw what happened to oblivious people and yet he saw what happened to fully aware people when it came to the supernatural. Neither option was safe but with Damon's help, Jenna would have the ultimate decision to make in the end.
And that's what Dean and Damon did; they gave Jenna a choice.
Everyone was waiting anxiously in the Gilbert's living room for Jenna to return home. She had been staying on campus to avoid everyone since Isobel had showed up at their doorstep a few nights ago. They were just waiting to see if Jeremy's text to his aunt is what would bring her back home.
Sure enough, the sound of a car door closing could be heard outside before the clicking of a lock was heard at the door shortly afterwards.
"Jeremy? I got your text, what's...wrong?" Jenna called out and trailed off at the end when she noticed the crowded living room.
What truly caught her attention were the two unknown men standing beside a tied up John with duct-tape over his mouth. She then noticed that Elena and Jeremy were sitting calmly on one of the couches while Alaric and Damon were standing along the back wall.
"What's going on? Why is John tied up?" Jenna questioned while slowly taking a step back. She couldn't understand how everyone she knew could be so calm while two strangers stood by a tied up man. Was this a robbery gone wrong?
"So he can listen and not interrupt what we're about to discuss." The shorter of the two strangers stated as he slowly approached Jenna with his hands up. "He's done enough damage as it is."
Jenna's brow furrowed out of confusion; she knew John was troublesome but what could he have done to anger two strangers? "What damage?"
"By bringing Isobel back to town." He continued while keeping his eyes on Jenna but noises of John trying to disagree could be heard from behind the approaching stranger. It got to a point that the taller stranger had to apply a bit of pressure to John's clavicle until he got the message to be quiet. Eventually he got it.
Jenna's breath hitched when she heard Isobel's name, a name that brought a lot of pain and betrayal to her heart. "I don't want to hear their excuses or their lies." She declared before she turned to walk away but she didn't get far until the first stranger's voice stopped her in her tracks.
"You're going to want to hear this because it has everything to do with Elena's safety." He firmly stated and he was pleased when Jenna stopped once Elena was mentioned. He knew if anything, bringing Elena into the conversation would grab the graduate student's attention.
Jenna turned back to glare at him. "Who did you say you were again?"
The stranger smirked as he continued to approach her. "I didn't but my name is Dean Winchester. I'm an old friend of Damon's and Ric's."
"Two people I happen to not like at the moment." Jenna declared with a scoff before she crossed her arms over her chest, as if she was getting ready for a stand down with this Dean Winchester guy.
Dean chuckled for her fiery attitude before the amusement was wiped from his face, something Jenna wasn't expecting so instantly. "That's a shame because I also happen to be Elena's biological father."
"But I thought..." She trailed off as her wide eyes moved between Dean, Elena and John. She was under the impression that John had been Elena's biological father but when her eyes landed on the tied up man in question, all she saw was a stunned expression which only confirmed to Jenna that John had believed that he was Elena's father from the start. What confused Jenna though was that Elena didn't look surprised by the news...Jenna could only conclude that another lie had been told to her.
Noticing Jenna's betrayed look to Elena, Dean hurried to explain enough to get Jenna to sit down and hear him out. "Only me and Isobel knew the truth of who Elena's father was and there is a reason for that. A reason that would explain any lie or excuse that was ever fed to you."
She didn't want to hear the explanation but a part of her had a feeling that she needed to. "Why do I get the feeling I'm not going to like this?"
Dean shrugged as he took his final steps towards Jenna. "You probably won't but we're giving you an option. If this gets too much for you, then just say the word and Damon will take it all away." He offered before he looked to Damon who only nodded; he and Dean had already discussed the option beforehand, even when everyone else was against Damon's involvement, especially Stefan.
"How?" She questioned while giving him a suspicious look. The option didn't seem plausible or realistic to her in anyway.
"It will be explained but just know that you have that option." Dean stated before he gestured for Jenna to take a seat.
Jenna sighed before she walked around to take an empty seat by Elena. "Okay, let me hear it." She declared with her full attention on Dean.
And so she did; Dean told Jenna everything, with Sam and the others (minus John) filling in a few things along the way. She didn't learn the extensive history of the Winchesters but she knew the basics of what they did and why Dean stayed away from Elena for as long as he did. Jenna learned about vampires, Isobel, Klaus and about the predestined fate that Elena had because she was born as the Petrova doppelganger. To say she was shocked was an understatement but to everyone's surprise, Jenna didn't want all the supernatural knowledge to be erased like Dean and Damon had offered her in the beginning.
After all that family drama was taken care of, Elena's bonding time with the Winchesters was much easier to pursue. There were quite a few times when Sam and Dean received invitations for dinner, from either Elena or Jenna, at the Gilbert house during their stay in Mystic Falls. It was a great way for both sets of families to get acquainted with one another. One of them happened to be a celebration of Sam's birthday when the time came which was a memorable experience for the hunter. Even Alaric had joined them as he and Jenna were mending their relationship now that she knew the truth.
Aside from those dinners, Elena would bond with Dean during his 'hunter lessons' as she's come to call them. He would either take her to practice her shooting or practice her fighting skills or he'd tell her stories about his past. When it came to Sam, Elena usually spend her time getting to know her uncle through academics. Whenever she needed some help with her homework, she always found herself going to him for some advice or help which usually came with his own stories about his life, whether it was about hunting, his time at Stanford or the very few times he wasn't involved in hunting at all. No matter which form of bonding she participated in, Elena found that she loved it. The only times anyone ever saw Elena without either Winchester was when she was at school with her friends. They all understood her need to spend time and get to know this new family she had discovered but it seemed to put a strain on Elena's relationship with Stefan since neither Winchester wanted anything to do with the youngest Salvatore vampire which was tough since they were all currently living under the same roof.
It's been three weeks after Klaus' demise and Elena found herself having another great day at the shooting range with Dean; she was improving her aim with every visit. They were currently driving back on a deserted road from Richmond after a productive morning of practicing since that was the closest shooting range place to Mystic Falls. At the moment, the music was practically nonexistent in the Impala yet it didn't seem like either passenger noticed as their attentions were focused on one another.
"Out of all the questions you could have asked and you ask me that." Dean stated with a shake of his head as his eyes remained on the road. It has become a thing of theirs that they'd treat their drives together as a 20-questions type thing. So far, it's been great.
Elena gave him an innocent smile from the passenger seat. "Like you said, I could ask you anything."
Dean rolled his eyes; immediately regretting ever giving her free-range on her questions. "You know...you are one weird kid Elena."
She shrugged. "Well what did you expect...I'm your kid after all." Elena teased easily. After three weeks of getting to know Dean, it had gotten to the point that she could easily state their connection but they both knew that Grayson Gilbert would still be Elena's father in her eyes. Dean was okay with that.
"That you are." Dean stated proudly with a laugh before he noticed a figure walking alongside the road up ahead.
"So are you going to tell me?" Elena pushed hopefully since it was a topic that Dean always deflected from. While on some level, she could understand why Dean didn't want to talk about it but her curiosity just wanted to know that part of him that she got to miss out on.
Unaware of the figure they just drove by, Elena was surprised when Dean pushed on the brakes before reversing the car back a few feet. She turned to see what he was looking at but when she found nothing but trees, she turned to face him.
"Are you okay?" She asked worriedly when she noticed that his face was a little pale.
"It's nothing." He said a few moments later before he turned around and started driving back to the boarding house in silence.
Unfortunately for Dean and Elena, their bonding was going to be cut short once they arrived at the boarding house. The two managed to find Sam on the couch with his laptop while Damon was making some more drinks by his beloved trolley cart of alcohol. Stefan had used Elena's absence as his chance to go hunting.
"Hey guys." Elena greeted as she and Dean ventured further into the room. Dean was still trying to wrap his head around what he saw earlier but his silence was starting to worry Elena.
"So did Buffy have a good time?" Damon quipped as he passed Elena a drink. He started nicknaming her Buffy once Dean started to train her in the basics in self-defense. There were a few times that he helped in those lessons if Dean needed Elena to practice with someone with a supernatural advantage.
Elena took the small glass but before she could drink it, Dean snagged it and gulped it down instantly. From an outsider, some may see this as Dean's way of stopping Elena from drinking but the intensity of the action caused Sam to worry.
"Dean, are you okay?" Sam questioned from his spot on the couch. Elena and Damon each gave the older Winchester a concerned look of their own.
Dean turned to face Sam with a blank look before Damon offered him another glass of his own. He took it with a nod before he focused on Sam again. "Yeah, I'm cool. What's up?"
Sam noticed the uncertainty but he didn't push it as he got started in telling Dean about a preschooler that went missing under some weird circumstances just recently, along with a few others over the last few weeks.
"Alright, so, uh, are you thinking demons?" Dean questioned as he moved to stand behind Sam so that he could see the online articles he found.
"Yeah, possibly, but...I mean, this stuff was major. These folks have nothing in common – no religious affiliations, different hometowns, all ages. Why would demons want them?" Sam elaborated yet it was obvious to Elena (who watched in silence) that he was stumped on finding a motive.
Dean shrugged. "Why do demons want anything?" He countered before he slapped Sam lightly on the shoulder. "Uh, so, are we on this?" He questioned yet his eyes trailed to Elena, as if he was gauging how well she'd take the news of them possibly leaving. He didn't want to leave but he knew that he had to.
Knowing where his brother's head would be at with a question like that, Sam looked to Elena as well.
With both Winchesters looking at her, Elena started to nibble on her lower lip. During one of her bonding sessions with Sam, she learned that he was trying to track down a prophet named Kevin who was their key in closing the gates of Hell forever. She knew it was an important mission and by the sounds of these missing cases, demons were involved which meant that Kevin could be involved somehow. On the one hand, she didn't want the Winchesters to leave but on the other hand, she knew that the Winchesters were needed to find those missing people. How could she get in the way of that?
"I guess duty calls for you guys." She sadly stated as she tried to give them a reassuring smile.
Sam sighed; he didn't like the idea of leaving his niece either...he couldn't image what Dean must be feeling about the idea. "Yep."
It was about an hour later when Sam and Dean were packed and ready to hit the road to Salina, Kansas, where the preschooler went missing. By then, it seemed like Elena had spread the word about their departure since all her friends and family who knew the Winchesters had come by the boarding house to say their goodbyes. The sight was odd for the Winchesters but deep down they were touched.
A majority of the group had thanked the Winchesters again for their hand in killing Klaus while those part of the Gilbert clan (minus John) had invited the Winchesters to come back whenever they wanted. Dean even asked Alaric to continue the basic training lessons that he had started with Elena; Alaric accepted.
Everyone was surprised however when it came time for Dean and Damon to say goodbye to each other. The hunter and vampire managed to exchange a one-arm hug with one another before Dean whispered to Damon to take care of his daughter and to not give up on her. Damon didn't hesitate in reassuring Dean that such a request didn't need to be asked before he pulled back. It shouldn't have surprised everyone but then again, not everyone knew of the time Damon and Dean had spent together hunting and building a working friendship almost a decade ago. The hunter then moved onto his daughter, leaving everyone wondering what was said between Damon and Dean; only a stunned Caroline knew since Stefan's animal diet had weakened his enhanced hearing quite a bit.
"I guess this is it." Dean stated, with his hand on the back of his neck as he walked with Elena to the front yard. He was never good at goodbyes, he always hated them and yet this one was the worst for him.
"You'll come back though...right?" Elena quietly asked even though it was such a loaded question to begin with.
Dean sighed. "I'll do my absolute best but I need you to do something for me Elena. Can you do that?" He wished that he could promise her that he would return but with his lifestyle, it wasn't easy to keep a returning promise like that.
"Anything." She said with a nod.
Dean tilted Elena's head up so he was looking directly into her eyes, so he could know that she was truly registering what it was he was saying and so that she could see how serious he was with his words. "If things get tough, I want you to always remember that there is always another way...you just have to fight and find it. And I don't need you sacrificing yourself ever again, you got it? You've got a full life ahead of you. I want you to embrace it and live it."
"I will." Elena agreed before blinking a couple of times; she was trying to hold back her tears.
"Because us Winchesters don't give up without a fight and I have a feeling that the Gilberts raised you with that same mentality." Dean continued before a smirked appeared on his face.
"You're damn right we were." Jeremy piped in with a mischievous smile on his face, causing everyone to laugh at his timed interruption.
Dean and Elena smiled and laughed a bit for the tension being broken before she hugged him tightly around his waist. He returned the hug before he placed a kiss on her forehead; it was getting to the point that his affections for his daughter came naturally to him.
"Be careful okay kiddo." He whispered to her before he pulled back and away from her.
"The same for you and Sam." She parroted back with a nod before she rushed to give Sam a quick hug.
The Winchesters then hopped into the Impala before they drove off, leaving the rest of the Mystic Falls gang to wave goodbye from the boarding house's front lawn.
Elena brushed away a lone tear just before it fell from her eyes when Damon walked to stand beside her. "Don't worry about them. They have survived much worse than a demon case. You'll see them again." He declared before he sipped on his newly acquired bourbon glass; he poured himself one during Dean's goodbye to Elena.
"How do you know?" Elena questioned after turning to look up at the vampire, who saw the need in her eyes for his words to be right.
Damon smiled softly at her, having no need to mock or use sarcasm for this moment. "Because death couldn't keep neither of them away from their family Elena, that's how I know they will return to you...because you are part of their family." He assured with finality and Elena couldn't help but smile for Damon's words because he was right. Sam and Dean have both gone to heaven and hell (and Purgatory in Dean's case), either for the other or for the sake of the world, and yet they still returned to Earth after it all. It was proof that either Winchester brother would fight to get back to their dysfunctional family; Elena just found some comfort in the fact that she was part of that Winchester family.