#╰––– » 「 ✞ 」 𝘃𝗲𝗿𝘀𝗲 𝗶𝗻𝗳𝗼. ┊ don't speak

[ripcrispyblonde]

when jess and sidney were together in her season 4 arc, after she's under the impression that sam was locked in the cage with michael and lucifer for eternity, after they worked a case together he would take her to the closest big city and they'd have a few nights pretending they were locals on a couple of date nights. because he tried it out after their first case and saw how much she benefited from simple distraction and the hustle and bustle of the city from growing up in san francisco

[crispyblonde]

Info is likely to expand, follows Jess being resurrected in late season 4 by Heaven

**Split into seasonal timeframes because this is longer than I anticipated.**

LATE SEASON 4

Jess found herself alive in a field in Falls Park in Sioux Falls, South Dakota. She didn’t have much time to think about her surroundings before a man appeared before her. A man that claimed to be an angel named Zachariah. He claimed that Sam needed her, that Heaven wanted to make good on what the demons jerking him around had done to her… that he was sorry nobody had stepped in to protect her. While her faith in God and any force of good had been severely shaken with her death and what she had seen in Heaven, a piece of her was still hopeful and believed him. With Bobby’s property warded from Heaven’s eyes, he says he can’t help her find Sam exactly, but they had been following the Winchester’s movements. They know Bobby Singer lived somewhere in this town and he would be able to help her find Sam.

If he were being honest, Heaven hadn’t bothered too much with finding Bobby’s place. Intervening with the Winchesters hadn’t really deemed necessary so far apart from the brothers trying to protect Anna Milton. However, they were not going to place all of their faith in Hell to break all of the seals to bring on the apocalypse and they had decided that Jess would be a great token of leverage over Sam. At the very least in the upcoming war between Michael and Lucifer that the Winchesters were still in the dark about. As quickly as the angel had appeared, he was gone, with what Jess would later recognize was a foreboding word that he would keep in touch. It didn’t take long at Phillips Avenue Diner for Jess to find out that Bobby owned a salvage yard on the outskirts of the city. She bummed a ride off of one of the guys in the diner. She was a bit jarred by the tests she was subject to at Bobby's behest, especially when she told him who she was. Holy water and salt were something the demon within Brady had lorded over Jessica when she stabbed him in the chest, goading her that she was far off base to save her own life.

At the time, the Winchesters were on their way back to Bobby’s after finding out that they had a half brother named Adam Milligan. Her reunion with Sam wasn’t quite what she expected. Something seemed off and she wasn’t sure what, so she plastered a signature smile on her face and held onto him as they both shed tears. Time had passed, even since she had last seen him in Heaven – and vowed to not see him again until he was there for good – so naturally, there would be a learning curve for the two of them to fit back together, right? Still a bit perturbed by how thoroughly she had been vetted, she kept the details of the brief meeting with the angel to herself. Instead talking about her time in Heaven knowing Ash, who had given her some information about the men before her in their talks. It was a hell of a lot more interesting to spend time with him than to relive any of her memories over again for the hundredth time. When Dean has the dream about meeting Castiel at a certain location, Jessica is left behind at Bobby’s, because despite the peaceful context of Dean’s dream his warning about the potential of others listening (even in Dean’s mind) was rather ominous. They agreed that it was for the best to not let Sam’s freshly resurrected college girlfriend out where there was a higher risk for something to happen to her without any self-defense or hunting training. So, Jessica remained at Bobby’s. She helped him clean up a bit and made a few nice homecooked meals for them both. She glazed through a few books about monsters, expressing an immediate interest in learning how to protect herself. However, it wasn’t long before Bobby got the call from Dean, detailing his discovery of Sam’s addiction to demon blood, facilitated by Ruby.

Disturbed by this information, she and Sam had a fight through the panic room door. He was having some weird, sexual, blood-drinking relationship with a demon to make himself stronger? A bit of her anger was selfish and a bit more was fueled by jealousy. She was upset that he would even think to trust, let alone have a relationship with a demon, when one had taken her away from him. The one they both thought was their friend. A distressed, jealousy-fueled Jessica told him that he wasn’t remotely close to the person that she had known at Stanford and she was not interested in sticking around while he begged for blood and probably begged to see Ruby. She had always had a habit of saying biting things she didn’t fully mean in the heat of the moment when she was angry. All but demanding a pair of keys for one of the okay cars at the salvage yard, she left with a bit of money in her pocket from Bobby.

SEASON 5

For two weeks, Jess was holed up in a motel room in Red Cloud, Nebraska. What was she supposed to do? Starting a normal life didn’t feel like an option because she couldn’t imagine living simply while her family was still grieving her loss, because there was no way she was telling them and bringing them into the dark underbelly of reality. It was at this point that Dean asked Castiel to find Jessica to ward her, like he had just done for the Winchesters to protect her from the rise of Lucifer. A terrified Jessica was backed into the corner of her motel room, tearfully begging the angel for her life. After Castiel placed his hand on her, a jolt of pain burned red hot through her ribs. It was then that he explained that he was an angel sent by Dean to protect her from other angels, now that Lucifer was roaming around. Castiel also gave her a cellphone that had the numbers of the Winchester brothers, Bobby, and a hunter named Ellen programmed into it. An unread text message to the phone from Dean detailed that she could reach out to any of these people for help if she needed it. She sent him a thank you text message, but stated she needed more time to herself.

After a couple more days, Jess ultimately decided that she was going to learn how to hunt. Knowing about the supernatural and how awful her death had been, she had decided there wasn’t an option for her other than to try and save others from fates similar to hers. She went to the local library and started researching strange deaths. It was easy to start with a headline involving animal attacks where the bodies seemed to be drained of blood. In the know of the supernatural now, it seemed like an obvious red flag for vampires and from what she could find about them, decapitation seemed to be the most reliable kill method. She traveled a few states over to Galena, Illinois. Long story short, despite her stealing a blade from a sporting goods store, she was in over her head with no formal training in combat. However, with a stroke of luck, she was saved by a hunter named Charlotte Perrin. The wealthy and well-known hunter took Jessica in under her wing, giving her training in fighting, a few needed weapons, and a small journal detailing information of what to look for in headlines for certain monsters and what their weaknesses were. Charlotte also made sure she got in touch with the Winchesters to let them know that the young woman was in good hands after Jessica drunkenly confessed most of her story to her – leaving Sam’s demon blood addiction out of it. That wasn't her story to tell and despite being upset with him, Jessica knew deep down that Sam didn't have an evil bone in his body. Something drew him to embracing that part of himself and it was to help people, not hurt them. But her anger had made her storm out and not let him explain -- and she was rather embarrassed about that. Her racing mind whenever she didn't have something to focus on berated herself for not taking a second to trust the man that she had loved and told her that she didn't deserve forgiveness for that. Sam deserved someone that loved and trusted him, didn't doubt that they knew who he was, even for a brief lapse in a blind jealous rage.

Jessica remained with Charlotte and/or her small network of hunters that she had gathered since Charlotte’s own story in to the supernatural began. Throughout this time period, Jessica tried to deal with nightmares about her death, fire, Sam, and visits from Zachariah in her dreams that were only met with hostility on her part. Distrust for Heaven had rubbed off on her in the few days she had been with Sam, Dean, and Bobby and if one thing was certain, she would not allow herself to be used as a pawn again. From time to time, Jessica would send Dean check in texts, but she had yet to see either of the Winchesters in person since she had run off. She struggled with what being alive again really meant for her, but most of all she struggled with the guilt of abandoning Sam when he clearly needed her. There wasn't a doubt in her mind that he wouldn't have reacted as she had if the roles were reversed... and how could she really face him after what she had said? Or what if he really had loved the demon more than her? One of those texts to Dean was met with a response that friends of the Winchesters had died in an attempt to kill Lucifer.

It has been about six months since Jess had talked to Sam. The more that time passed and the sting of jealousy started to wear off, the more that she felt guilty for how she had behaved. Sam deserved more unconditional love than she had given him – but this only fueled her feelings that she didn’t deserve forgiveness for that. Therefore, the concept of any communication with Sam built itself up in her head to become something huge that she was terrified to face. The elder Winchester still hadn’t told Sam that he had given Jessica the phone and that they were in sporadic contact, partially at Jess’s request. Dean wanted to respect her healing time, but the guilt of keeping her a secret from his brother was weighing on him, especially when he also had reconnected with his brother after three months apart. The information of the boys grieving their friends Ellen and Jo Harvelle, however, was enough for Jessica to say goodbye to Charlotte, but not without an insistence of a parting gift of ten grand and Jess’s promise to tell the Winchesters she sent them their best.

She showed up at Bobby’s and she and Sam talked for a long time. She apologized for what she had said and how her own fear had spiraled and kept her away for the last few months. She knew Sam’s heart and after being taken out of the heat of the moment and all of the overwhelming feelings of being alive again and thrust into chaos, she knew his heart had to have been in the right place, even if all of his senses should have been telling him better than to trust a demon’s intentions. Being the reason that Lucifer was freed from the cage seemed like punishment enough. The pair slowly let themselves reconnect and she tried to soothe over the conflict between the two brothers about the fact that she and Dean had still communicated from time to time in the last six months. After this, she remained beside them through everything, both of the brothers a bit impressed with the hunter that Charlotte had already molded her into. Her propensity to hold information back from Sam bit her in the ass once again when they came face to face with the demon inside of Tyson Brady, now the Horseman’s stable boy. The sight of Brady alone caused Jessica to get physically ill, let alone his goading, and the conversation of why she would have let him continue to believe Azazel had killed her wasn’t easy either.

Then, about six months after she and Sam were reunited, he made the difficult decision that he needed say yes to Lucifer and put a stop to the looming apocalypse. Sam was convinced in his strength to trap the devil back in the cage. This mission, was of course, was suicide for Sam and despite Jessica’s pleas he insisted that he needed to put a stop to what his actions had started. A tearful Jess left the boys and Bobby while they’re still planning out the attack after a tender night with Sam. She didn’t say goodbye in person, rather she left a letter detailing her love for Sam and that she could not watch his death happen. She traveled to The Crossroads, a newly opened hunter bar in Smith Center, Kansas to meet up with Charlotte. Here she quickly befriended the co-owners Teddy Bristol and Cameron Ambrose, though Cam was always quick to say that Teddy was the true owner – he had just put some of the money up. A visit from Dean at the bar confirmed that Sam had pulled it off and that Lucifer, Michael, and Adam were locked in the cage with him. She encouraged Dean to go to Lisa, that she would be okay on her own, shrugging off the elder's protests that Sam would want her to move on to a normal life too. Cameron stayed with her to drink after he had closed down the bar that night and they became fast friends. While nothing happened between them that night, they did end up sleeping together a couple of times after a few months of Jess's grieving.

SEASON 6+

Jessica and Dean continued their sporadic contact throughout his time with Lisa, the two often communicating about potential ideas to spring Sam from the cage, but after a couple of months of dead ends it really started to feel like Sam’s actions were truly final. Using her money from Charlotte and tips from sporadic nights of helping Cam and Teddy cover the bar, she continued to hunt. Every so often, she was in contact with Bobby, but he kept her at an arm’s length after the resurrected Sam had started poking his head around. Bobby could tell something wasn’t right with him, despite testing him in all of the ways he could imagine and Jessica had been through enough. About eight months after Sam had died, Jess had slept with Sidney Carmichael for the first time. What first was meant to be a one night stand developed into something more after her nightmares woke him up and how lost and alone she felt caused her to open up to him. She and Sidney hunted together some, but Jess also took cases of her own or helped out when any of the hunters she had met needed an extra pair of hands, always determined to add more information to her monster journal. More information about the timeline of Jess and Sidney's relationship is detailed here.

Despite her budding relationship with Sidney, when she got the news from Dean that Sam was alive, Jessica dropped everything to meet up with them. An excited Jessica was met with another reunion that didn’t feel right. For a bit, Sam tried to play along, like he knew he ought to, but it wasn’t more than a week or two before Jessica caught him making out with some girl outside of a bar while she was helping Dean with some research. Her abandonment of him in his last moments was an easy scapegoat, along with trying to keep her emotions hidden and not telling him about Brady. Not to mention, he had heard through the hunter grapevine of her less than platonic relationships with Cameron and now Sidney. Without a soul, he hoped that the sting would keep her away from him so he would be unbridled to do whatever he pleased. It worked, of course, after Jessica had gotten some harsh words of her own in about not even trying to find her when he found himself alive again almost immediately. Jessica had forgiven him for that – only for her mistakes (among other things) to be thrown back in her face. She returned to The Crossroads and Cam held her while she cried on the back porch, despite her protests of wanting to be left alone.

She remained hunting, bouncing between hunting partners. At this point in time, Jessica was an established hunter of her own. Her relationship with Sidney was a bit rocky because she had dropped everything so quickly to see Sam, but they rekindled after a few weeks because Sidney really loved her. Sam called Jess when he gets his soul back. Jess had already met with Dean, where he explained that it was best to not talk about Sam’s time when he was soulless because he didn’t remember any of it… and breaking down the wall to those memories would send him into a torturous tailspin with the memories of Lucifer and Michael in the cage. When she reunited with Sam this time, it felt very reminiscent of when she had met up with him after Ellen and Jo’s death. A lot of emotions and still holding some things back from him – but at least she knew it was really the Sam she loved. After this, she remains by Sam’s side permanently, a little over two and a half years from the time she was resurrected. Jess keeps close contact with her hunter friends, especially Cam, Teddy, Charlotte, and Sidney's sisters Roxie and Teegan.

I may add further season information here later, but this is the primary footing of her rollercoaster ride before getting into a stable place with Sam.

[letmedeleteitplz]

Info is likely to expand, follows Jess being resurrected in late season 4 by Heaven

**Split into seasonal timeframes because this is longer than I anticipated.**

LATE SEASON 4

Jess found herself alive in a field in Falls Park in Sioux Falls, South Dakota. She didn’t have much time to think about her surroundings before a man appeared before her. A man that claimed to be an angel named Zachariah. He claimed that Sam needed her, that Heaven wanted to make good on what the demons jerking him around had done to her… that he was sorry nobody had stepped in to protect her. While her faith in God and any force of good had been severely shaken with her death and what she had seen in Heaven, a piece of her was still hopeful and believed him. With Bobby’s property warded from Heaven’s eyes, he says he can’t help her find Sam exactly, but they had been following the Winchester’s movements and they know Bobby Singer lived somewhere in this town and he would be able to help her find him.

If he were being honest, Heaven hadn’t bothered too much with finding Bobby’s place. Intervening with the Winchesters hadn’t really deemed necessary so far apart from them trying to protect Anna Milton from them. However, they were not going to place all of their faith in Hell for breaking all of the seals and they had decided that Jess would be a great token of leverage over Sam at the very least in the upcoming war that the Winchesters were still in the dark about. As quickly as the angel had appeared, he was gone with what Jess would later recognize was a foreboding word that he would keep in touch. It didn’t take long at Phillips Avenue Diner for Jess to find out that Bobby owned a salvage yard on the outskirts of the city. She bummed a ride off of one of the guys in the diner and was a bit jarred by the tests she was subject to, especially when she told him who she was.

At the time, the Winchesters were on their way back to Bobby’s after finding out that they had a half brother named Adam Milligan. Her reunion with Sam wasn’t quite what she expected. Something seemed off and she wasn’t sure what, but she plastered a signature smile on her face. Still a bit perturbed by how thoroughly she had been vetted, she kept the meeting with the brief meeting about the angel to herself, instead talking about her time in Heaven knowing Ash, who had given her more information about Bobby during all of their talks. When Dean has a dream about meeting Castiel at a certain location, Jessica is left behind at Bobby’s, because despite the peaceful context of Dean’s dream his warning about the potential of other’s listening even in Dean’s mind was rather ominous and Sam wasn’t letting his freshly resurrected college girlfriend out where there was a higher risk for something happening to her.

So, Jessica remained at Bobby’s. She helped him clean up a bit and made a few nice homecooked meals for them both before Bobby gets the call from Dean about how he had found out about Sam’s addiction to demon blood, facilitated by Ruby. Perturbed by this information, she and Sam had a fight through the panic room door. He was having some weird sexual, blood-drinking relationship with a demon to make himself stronger? A bit of her anger was selfish and a bit more fueled by jealousy. She was upset that he would even think to trust, let alone have a relationship with a demon when one had taken her away from him. Jessica told him that he wasn’t remotely close to the person that she had known at Stanford and she was not interested in sticking around while he begged for blood and probably begged to see her. All but demanding a pair of keys for one of the okay cars at the salvage yard, she left with a bit of money in her pocket from Bobby.

SEASON 5

For two weeks, Jess was holed up in a motel room in Red Cloud, Nebraska. What was she supposed to do? Starting a normal life didn’t feel like an option because she couldn’t imagine living simply while her family was still grieving her loss, because there was no way she was telling them and bringing them into the dark underbelly of reality. It was at this point that Dean asked Castiel to find Jessica to ward her, like he had just done for the Winchesters to protect her from the rise of Lucifer. A terrified Jessica was backed into the corner of her motel room, tearfully begging for her life after Castiel appeared and placed his hand on her, sending a jolt of pain through her ribs. He explained that he was an angel sent by Dean to protect her from angels, now that Lucifer was roaming around. Castiel also gave her a phone with his and Sam’s number programmed in it, attached with a promise that he would help her with whatever she needed.

After a couple more days, Jess ultimately decided that she was going to learn how to hunt. Knowing about the supernatural and how awful her death had been, she couldn’t fathom not trying to save others from fates similar to hers. She went to the local library and started researching strange deaths. It was easy to start with one involving animal attacks where the bodies seemed to be drained of blood. In the know of the supernatural now, it seemed like an obvious red flag for vampires and from what she could find about them, decapitation seemed to be the most reliable kill method. She traveled a few states over to Galena, Illinois. Long story short, despite her stealing a blade from a sporting goods store, she was in over her head with no formal training in combat. However, with a stroke of luck, she was saved by a hunter named Charlotte Perrin. The prosperous hunter took Jessica in under her wing, giving her training in fighting, a few needed weapons, and a small journal detailing information of what to look for in headlines for certain monsters and what their weaknesses were.

Jessica remained with Charlotte and/or her small network of hunters that she had gathered since her own story in to the supernatural began. Throughout this time period, Jessica tried to deal with nightmares about her death, fire, Sam, and visits from Zachariah in her dreams that were met with hostility. until she had called Dean just to check in on him and Sam. Close friends of the Winchesters had just died in an attempt to kill Lucifer. It has been about six months since Jess had last seen Sam at this point. The elder Winchester still hadn’t told Sam that he had given Jessica the phone and that they were in sporadic contact, partially at Jess’s request. She had still torn up about everything with Sam and wasn’t ready to forgive him yet and Dean wanted to respect her healing time, but the guilt of keeping her a secret from his brother was weighing on him, especially when he reconnected with his brother after three months. The information of the boys grieving their friends Ellen and Jo Harvelle, however, was enough for her to say goodbye to Charlotte, but not without an insistence of a parting gift of ten grand and Jess’s promise to tell the Winchesters she sent them their best.

She showed up at Bobby’s and she and Sam talked for a long time, she apologized for what she had said. It had been weighing heavy on her mind. She knew Sam’s heart and could see that it had been in the right place, even if all of his senses should have been telling him better than to trust a demon’s intentions. Being the reason that Lucifer was freed from the cage seemed like punishment enough. The pair slowly let themselves reconnect and she tried to soothe over the conflict between the two brothers about the fact that she and Dean had still communicated from time to time. After this, she remained beside them through everything, both of the boys a bit impressed with the hunter that Charlotte had already molded her into. Her propensity to hold information back from Sam bit her in the ass once again when they came face to face with the demon inside of Tyson Brady, now the Horseman’s stable boy. The sight of Brady alone caused Jessica to get physically ill, let alone his goading, and the conversation of why she would have let him continue to believe Azazel had killed her wasn’t easy either.

Then, about six months after she and Sam were reunited he had decided that he needed to be the one to say yes to Lucifer because he was convinced in his strength to trap the devil back in the cage. This mission, was of course, suicide for Sam and despite Jessica’s pleas he insisted that he needed to do what was right for the world, that without him doing this the whole world would be thrown into an apocalypse through the fight of Lucifer and Michael. A tearful Jess left the boys and Bobby while they’re still planning out the attack. She traveled to The Crossroads, a newly opened hunter bar in Smith Center, Kansas where she quickly befriended the co-owners Teddy Bristol and Cameron Ambrose, though Cam was always quick to say that Teddy was the true owner – he had just put some of the money up. After a visit from Dean at the bar confirmed that Sam had pulled off the stunt, she encouraged him to go to Lisa, that she would be okay on her own. Cameron stayed with her to drink after he had closed down the bar and the two drunkenly hooked up, the first of a budding friends with benefit relationship.

SEASON 6+

Jessica and Dean continued their sporadic contact throughout his time with Lisa, the two often communicating about how they could maybe spring Sam from the cage, but Jess all but gave up after a couple of months. Using her money from Charlotte and tips from sporadic nights of helping Cam and Teddy cover the bar, she continued to hunt. Every so often, she was in contact with Bobby, but he kept her at an arm’s length after the resurrected Sam had started poking his head around. Bobby could tell something wasn’t right with him, despite testing him in all of the ways he could imagine. About eight months after Sam had died, Jess had slept with Sidney Carmichael for the first time. What first was meant to be a one night stand developed into something more, when waking him up from her nightmares led her to open up to him. She and Sidney hunted together some, but Jess also took cases of her own or helped out when any of the hunters she had met needed an extra pair of hands.

However, when she got the news from Dean that Sam was alive she dropped everything to meet up with them to only be met with another reunion that didn’t feel right. For a bit, he tried to play along like he knew he ought to, but it wasn’t more than a week or two before Jessica caught him making out with some girl outside of a bar while she was helping Dean with some research. He explained that he couldn’t get over how he’d abandoned him in his last moments and continually lied to his face, and had since admitted to her more significant relationships since his supposed passing. Without a soul, he hoped that the sting would keep her away from him so he would be unbridled to do whatever he pleased. It worked, of course, after Jessica had gotten some harsh words of her own in about not even trying to find her when he found himself alive again. She returned to The Crossroads and Cam held her while she cried on the back porch, despite her protests.

She remained hunting, bouncing between hunting partners. At this point in time, Jessica was an established hunter of her own. Her relationship with Sidney was a bit rocky because she had dropped everything so quickly to see Sam, but they rekindled a couple of times. Sam called Jess when he gets his soul back and Jess had already gotten a warning from Dean that it was best to not talk about Sam’s time when he was soulless because he didn’t remember any of it and breaking down the wall to those memories would send him into a torturous tailspin with the memories of Lucifer and Michael in the cage. When she reunited with Sam this time, it felt very reminiscent of when she had met up with him after Ellen and Jo’s death. After this, she remains by Sam’s side, a little over two and a half years after she was resurrected. Jess keeps close contact with her hunter friends, especially Cam, Teddy, and Charlotte.

I may add further season information here later, but this is the primary footing of her rollercoaster ride before getting into a stable place with Sam.

[ripcrispyblonde]

I will forever have brainrot for the Zachariah late season 4 res arc. Thinking about Jess within the hunting community when she isn't with Sam. She's mad at him because of the demon blood and then she thinks he's dead for months and then he's back without his soul. But she's in immediate attack mode no matter what state their relationship is in whenever she hears another hunter say anything remotely negative about him. Much to eventual chagrin of her hunter friends that are with her because she's picking fights with anyone.

For example, when she falls into her relationship with Sidney Carmichael he learns quick that Sam's name stays out of his mouth. Especially after she dropped everything when she found out Sam was alive again only to come crawling back to Sidney when Sam's soullessness gets in the way of a happy reunion.

[ripcrispyblonde]

jess in the season 4 res arc doesn't have any romantic or sexual encounters until a few months after the lucifer/michael showdown. she's upset about the demon blood for her own somewhat selfish and jealous reasons. most of her time between then and her reunion with sam after ellen and jo's death is spent with charlotte perrin. had some run-ins with sidney and his siblings as well as teddy and cam as they were prepping/starting to open the crossroads.

a few months after sam's death she and cam had a few nights together, but it was more casual. as she intended sidney to be when they hooked up for the first time eight months after sam went in the cage, but it developed into more than that without either of them initiating that conversation about what they were. roxie definitely tried to warn jess off of her brother more than once. and charlotte tried to pass of subtle judgments back when they were simply hunting contacts before sam's death. jess brushed them both off, insisting that sidney's more than people see.

[ripcrispyblonde]

the amount of crap the walls of the crossroads and their patrons see in jess's late season 4 res arc is definitely staggering. her messy emotions and way too much p!nk karaoke.

[ripcrispyblonde]

Info is likely to expand, follows Jess being resurrected in late season 4 by Heaven

**Split into seasonal timeframes because this is longer than I anticipated.**

LATE SEASON 4

Jess found herself alive in a field in Falls Park in Sioux Falls, South Dakota. She didn't have much time to think about her surroundings before a man appeared before her. A man that claimed to be an angel named Zachariah. He claimed that Sam needed her, that Heaven wanted to make good on what the demons jerking him around had done to her... that he was sorry nobody had stepped in to protect her. While her faith in God and any force of good had been severely shaken with her death and what she had seen in Heaven, a piece of her was still hopeful and believed him. With Bobby's property warded from Heaven's eyes, he says he can't help her find Sam exactly, but they had been following the Winchester's movements and they know Bobby Singer lived somewhere in this town and he would be able to help her find him.

If he were being honest, Heaven hadn't bothered too much with finding Bobby's place. Intervening with the Winchesters hadn't really deemed necessary so far apart from them trying to protect Anna Milton. However, they were not going to place all of their faith in Hell to break all of the seals to bring on the apocalypse and they had decided that Jess would be a great token of leverage over Sam. At the very least in the upcoming war between Michael and Lucifer that the Winchesters were still in the dark about. As quickly as the angel had appeared, he was gone, with what Jess would later recognize was a foreboding word that he would keep in touch. It didn't take long at Phillips Avenue Diner for Jess to find out that Bobby owned a salvage yard on the outskirts of the city. She bummed a ride off of one of the guys in the diner. She was a bit jarred by the tests she was subject to, especially when she told him who she was. Holy water and salt were something the demon within Brady had lorded over Jessica when she stabbed him in the chest, goading her that she was far off base to save her own life.

At the time, the Winchesters were on their way back to Bobby's after finding out that they had a half brother named Adam Milligan. Her reunion with Sam wasn't quite what she expected. Something seemed off and she wasn't sure what, so she plastered a signature smile on her face and held onto him as she shed some tears. Time had passed, even since she had last seen him in Heaven -- and vowed to not see him again until he was there for good -- so naturally, there would be a learning curve for the two of them to fit back together, right? Still a bit perturbed by how thoroughly she had been vetted, she kept the details of the brief meeting with the angel to herself. Instead talking about her time in Heaven knowing Ash, who had given her some information about the men before her in their talks. When Dean has the dream about meeting Castiel at a certain location, Jessica is left behind at Bobby's, because despite the peaceful context of Dean's dream his warning about the potential of others listening even in Dean's mind was rather ominous. They agreed that it was for the best to not let Sam's freshly resurrected college girlfriend out where there was a higher risk for something to happen to her. So, Jessica remained at Bobby's. She helped him clean up a bit and made a few nice homecooked meals for them both. She glazed through a few books about monsters, expressing an immediate interest in learning how to protect herself. However, it wasn't long before Bobby got the call from Dean, detailing his discovery of Sam's addiction to demon blood, facilitated by Ruby.

Disturbed by this information, she and Sam had a fight through the panic room door. He was having some weird, sexual, blood-drinking relationship with a demon to make himself stronger? A bit of her anger was selfish and a bit more was fueled by jealousy. She was upset that he would even think to trust, let alone have a relationship with a demon, when one had taken her away from him. A distressed Jessica told him that he wasn't remotely close to the person that she had known at Stanford and she was not interested in sticking around while he begged for blood and probably begged to see Ruby. She had always had a habit of saying biting things she didn't fully mean in the heat of the moment. All but demanding a pair of keys for one of the okay cars at the salvage yard, she left with a bit of money in her pocket from Bobby.

SEASON 5

For two weeks, Jess was holed up in a motel room in Red Cloud, Nebraska. What was she supposed to do? Starting a normal life didn't feel like an option because she couldn't imagine living simply while her family was still grieving her loss, because there was no way she was telling them and bringing them into the dark underbelly of reality. It was at this point that Dean asked Castiel to find Jessica to ward her, like he had just done for the Winchesters to protect her from the rise of Lucifer. A terrified Jessica was backed into the corner of her motel room, tearfully begging the angel for her life. After Castiel placed his hand on her, a jolt of pain burned red hot through her ribs. He explained that he was an angel sent by Dean to protect her from other angels, now that Lucifer was roaming around. Castiel also gave her a cellphone that had the numbers of the Winchester brothers, Bobby, and a hunter named Ellen programmed into it. An unread text message to the phone from Dean detailed that she could reach out to any of these people for help if she needed it. She sent him a thank you text message, but stated she needed more time to herself.

After a couple more days, Jess ultimately decided that she was going to learn how to hunt. Knowing about the supernatural and how awful her death had been, she had decided there wasn't an option for her other than to try and save others from fates similar to hers. She went to the local library and started researching strange deaths. It was easy to start with one involving animal attacks where the bodies seemed to be drained of blood. In the know of the supernatural now, it seemed like an obvious red flag for vampires and from what she could find about them, decapitation seemed to be the most reliable kill method. She traveled a few states over to Galena, Illinois. Long story short, despite her stealing a blade from a sporting goods store, she was in over her head with no formal training in combat. However, with a stroke of luck, she was saved by a hunter named Charlotte Perrin. The wealthy and well-known hunter took Jessica in under her wing, giving her training in fighting, a few needed weapons, and a small journal detailing information of what to look for in headlines for certain monsters and what their weaknesses were. Charlotte also made sure she got in touch with the Winchesters to let them know that the young woman was in good hands after Jessica drunkenly confessed most of her story to her -- leaving Sam's demon blood addiction out of it. Jessica remained with Charlotte and/or her small network of hunters that she had gathered since Charlotte's own story in to the supernatural began. Throughout this time period, Jessica tried to deal with nightmares about her death, fire, Sam, and visits from Zachariah in her dreams that were only met with hostility from her part. Distrust for Heaven had rubbed off on her and if one thing was certain, she would not allow herself to be used as a pawn again. From time to time, Jessica would send Dean check in texts, but she had yet to see either of the Winchesters in person since she had run off. One of those texts was met with a response that friends of the Winchesters had died in an attempt to kill Lucifer.

It has been about six months since Jess had talked to Sam. The more that time passed and the sting of jealousy started to wear off, the more that she felt guilty for how she had behaved. Sam deserved more unconditional love than she had given him -- but this only fueled her feelings that she didn't deserve forgiveness for that. Therefore, the concept of any communication with Sam built itself up in her head to become something huge that she was terrified to face. The elder Winchester still hadn't told Sam that he had given Jessica the phone and that they were in sporadic contact, partially at Jess's request. Dean wanted to respect her healing time, but the guilt of keeping her a secret from his brother was weighing on him, especially when he reconnected with his brother after three months. The information of the boys grieving their friends Ellen and Jo Harvelle, however, was enough for her to say goodbye to Charlotte, but not without an insistence of a parting gift of ten grand and Jess's promise to tell the Winchesters she sent them their best.

She showed up at Bobby's and she and Sam talked for a long time. She apologized for what she had said and how her own fear had spiraled and kept her away for the last few months. It had been weighing heavy on her mind. She knew Sam's heart and after being taken out of the heat of the moment, she could see that it had been in the right place, even if all of his senses should have been telling him better than to trust a demon's intentions. Being the reason that Lucifer was freed from the cage seemed like punishment enough. The pair slowly let themselves reconnect and she tried to soothe over the conflict between the two brothers about the fact that she and Dean had still communicated from time to time. After this, she remained beside them through everything, both of the boys a bit impressed with the hunter that Charlotte had already molded her into. Her propensity to hold information back from Sam bit her in the ass once again when they came face to face with the demon inside of Tyson Brady, now the Horseman's stable boy. The sight of Brady alone caused Jessica to get physically ill, let alone his goading, and the conversation of why she would have let him continue to believe Azazel had killed her wasn't easy either.

Then, about six months after she and Sam were reunited, he made the difficult decision that he needed say yes to Lucifer and put a stop to the looming apocalypse. Sam was convinced in his strength to trap the devil back in the cage. This mission, was of course, was suicide for Sam and despite Jessica's pleas he insisted that he needed to put a stop to what his actions had started. A tearful Jess left the boys and Bobby while they're still planning out the attack after a tender night with Sam. She didn't say goodbye in person, rather she left a letter detailing her love for Sam and that she could not watch his death happen. She traveled to The Crossroads, a newly opened hunter bar in Smith Center, Kansas to meet up with Charlotte. Here she quickly befriended the co-owners Teddy Bristol and Cameron Ambrose, though Cam was always quick to say that Teddy was the true owner -- he had just put some of the money up. After a visit from Dean at the bar confirmed that Sam had pulled it off and that Lucifer, Michael, and Adam were locked in the cage with him. She encouraged him to go to Lisa, that she would be okay on her own. Cameron stayed with her to drink after he had closed down the bar that night, while nothing happened between them that night, it was the start of a budding friends with benefits relationship.

SEASON 6+

Jessica and Dean continued their sporadic contact throughout his time with Lisa, the two often communicating about potential ideas to spring Sam from the cage, but after a couple of months of dead ends it really started to feel like Sam's actions were truly final. Using her money from Charlotte and tips from sporadic nights of helping Cam and Teddy cover the bar, she continued to hunt. Every so often, she was in contact with Bobby, but he kept her at an arm's length after the resurrected Sam had started poking his head around. Bobby could tell something wasn't right with him, despite testing him in all of the ways he could imagine and Jessica had been through enough. About eight months after Sam had died, Jess had slept with Sidney Carmichael for the first time. What first was meant to be a one night stand developed into something more after her nightmares woke him up and how lost and alone she felt caused her to open up to him. She and Sidney hunted together some, but Jess also took cases of her own or helped out when any of the hunters she had met needed an extra pair of hands, always determined to add more information to her monster journal.

However, when she got the news from Dean that Sam was alive, she dropped everything to meet up with them. An excited Jessica was met with another reunion that didn't feel right. For a bit, he tried to play along, like he knew he ought to, but it wasn't more than a week or two before Jessica caught him making out with some girl outside of a bar while she was helping Dean with some research. Her abandonment of him in his last moments was an easy scapegoat, along with trying to keep her emotions hidden and not telling him about Brady. Not to mention, he had heard through the hunter grapevine of her less than platonic relationships. Without a soul, he hoped that the sting would keep her away from him so he would be unbridled to do whatever he pleased. It worked, of course, after Jessica had gotten some harsh words of her own in about not even trying to find her when he found himself alive again almost immediately. Jessica had forgiven him for that -- only for her mistakes (among other things) to be thrown back in her face. She returned to The Crossroads and Cam held her while she cried on the back porch, despite her protests of wanting to be left alone.

She remained hunting, bouncing between hunting partners. At this point in time, Jessica was an established hunter of her own. Her relationship with Sidney was a bit rocky because she had dropped everything so quickly to see Sam, but they rekindled a couple of times. Sam called Jess when he gets his soul back. Jess had already met with Dean, where he explained that it was best to not talk about Sam's time when he was soulless because he didn't remember any of it... and breaking down the wall to those memories would send him into a torturous tailspin with the memories of Lucifer and Michael in the cage. When she reunited with Sam this time, it felt very reminiscent of when she had met up with him after Ellen and Jo's death. A lot of emotions and still holding some things back from him -- but at least she knew it was really the Sam she loved. After this, she remains by Sam's side permanently, a little over two and a half years from the time she was resurrected. Jess keeps close contact with her hunter friends, especially Cam, Teddy, and Charlotte.

I may add further season information here later, but this is the primary footing of her rollercoaster ride before getting into a stable place with Sam.

[ripcrispyblonde]

Officially, I'm incorporating Jess’s Bella Swan moment is in the Season 4 resurrection arc. When she first meets Cameron Ambrose, bartender at The Crossroads. While she has money to get her own vehicle because of Charlotte Perrin’s generosity when she had helped Jess gain her footing in hunting, Cam insists Jess save her money for gas, weapons, motel rooms, food, etc down the line because he had come into possession of a newer truck when one of the hunting regulars had been killed on a case.

She is also given this truck in the Season 10 resurrection arc. While she is still freshly working cases with Azrael, Jess befriends Cam at the bar when she and Azzie go or when Azzie is away on angel duties. Driving a clunker she'd been able to take from a salvage yard, he decided to give her a more stable car.

It’s a 1983 GMC High Sierra Wideside still in great condition. She calls her Ladybug. Cam and Teddy help her keep the truck in good shape.

pov: jess having her bella swan moment™