How Do You Love Someone

Chapter Fifteen

Chapter Fifteen:

Ryder couldn't do this anymore. She had to just do it no matter how stupid it was. Ever since the siren case, she felt a little distant from Jenna. Not that Jenna noticed, if anything she thought Ryder was just stressing about the trials. Which was true on some level, but knowing how she truly felt about her, kind of hurt Ryder deeply. They have been friends for three years, and to find out that her best friend really hated her cut deep.

Dean noticed the way Ryder was acting, and although she hid it well he saw right through it. He knew the signs, after all he's been doing it for years, and it just made him feel that much bad for her. He still loved Jenna, and that would never change, but to see the way her words hurt Ryder was hard to see.

Sam came into the motel room on the phone, and by the what he was saying, it seemed he was talking to Bobby.

"What's up?" Dean asked looking up from Sam's laptop.

Sam kissed his wife and daughter, and frowned a little when he saw that she wasn't looking too good. He heard the shower on, and figured that Jenna was in there. He sat at the table with Dean. "I just talked to Bobby. He found something in Wyoming." He takes the laptop from Dean, and starts typing. Dean makes a face, which Ryder giggles at. After a few minutes, he looks up at his brother. "It's a small town, and no one's died in about two weeks."

Dean looks at him, not getting the connection. "Is that a bad thing?"

Sam explains the cases to Dean, while Ryder plays with Lilith. She kept thinking to herself that she had to do it, that there was no more waiting. As much as she loved her family, and wanted nothing more than to be with them this was something that she had to do. In the end, it'll be okay. She just had to survive it first.

Jenna came out of the shower, and when she looked at Ryder she couldn't help but remember what she said to her. No matter how many times she told herself or was told that it was the siren talking and not her, she couldn't help but think maybe it was. She couldn't help but get the feeling that there was more to it than what she was told, but if no one was talking than maybe it's nothing. She shrugged her shoulders, oh well.

They all eventually packed up and started to hit the road to Wyoming. She didn't want to make it too obvious, but she didn't want to sit in the back with Jenna, so Sam offered to sit in the back with her and Lilith.

Coming to their new motel for the the case, Ryder wasn't paying too much attention to the case the boys were working on, only focusing on her mission: the second trial. She would be lying if she said she wasn't scared. She was. She was scared that she would fail, scared that she wouldn't be able to complete the trials. After this, one more and then it'll all be over.

The boys got dressed to go interview the man who was shot point blank, and when they left Ryder got dressed as well. She would need to leave as soon as they got back. She just didn't know how to tell them. Now that it was too late to stop her, they would have no choice but to let her go. As much as she didn't want to tell them about the second trial, she knew she had to. Sam was her husband, and that alone gave him the right to know everything she was doing. After all, this was important.

"Jenna?" Jenna looked at her from the TV, "Do you know what episode this is?"

"Yeah. This is where there aren't any reapers taking the dying." Jenna didn't know where this was going.

"Yeah, so I'm going to need you to watch Lilith for awhile. Make sure you protect her." Ryder ordered.


Ryder sighed. "It's time I did the second trial."

Jenna didn't know what to say for a few moments. "Do you know who you have to save?" They haven't talked much about the who they had to save in order to complete the trial.

Ryder shook her head. "No, but time's running out. If I wait to find out who I have to save, it'll be too late. Not to mention I still have one more trial to do."

She was right, and Jenna knew that. After some time just staring everywhere but each other, Jenna nods her head. "Okay, but you better come back. We all need you here." Jenna says with a sincere looking smile.

After thinking back to the siren, Ryder had a hard time believing her. She put on a smile that looked incredibly convincing. She had years of practice, and it never failed her. In the past, Jenna could see through all the false smiles and masks, but now she was just like everybody else. And in Ryder's book, that wasn't a good thing.

A couple hours later, and the door opened to Sam and Dean. They looked a little tired, and they began taking off their coats. Sam was taking off his jacket when he saw that Ryder was getting dressed.

"Going somewhere?" Sam asked throwing his jacket over a chair. Dean heard that and looked at Ryder as well.

Ryder took a deep breath. "I have to do the second trial now. Time's running out."

Sam was afraid of this. It had been awhile since the topic of the trials have been brought up. It had been several months since his wife had done the first trial.

"What is it?" asked Dean.

"I have to rescue an innocent soul and deliver them unto Heaven." Ryder was running out of clean shirts, so she grabbed one of Sam's button ups to put over her tank top.

"How are you going to rescue an innocent soul? From where?" asked Dean.

She wasn't ready for this part. "From Hell." Sam and Dean couldn't breathe at that point. "I have to go to Hell and save an innocent soul."

"Are you freaking kidding me?! You have to go Hell? That's insane!" Dean yelled. She was expecting that from him, after all just at the beginning of all this Dean had just come from there.

Sam shook his head, "No, you're not going to Hell." He couldn't believe this. Why would they make the trial going to Hell?

"I'm going. I have to do this, because no one else is going to." Before Dean could say anything, she put up her hand to silence him, "And I'm not letting you wait four years to try to do this." It's not like you'll do it anyway.

"It's dangerous, and you could get hurt." Why couldn't she understand?

Ryder finished tying up her boots, and put her hair up with her bandana. "I understand that, but this is important. If I don't do this, do you have any idea what damage leaving Hell open would cause the world? What it could cause you two?" She shook her head. "No, I'm not letting it happen!"

After twenty minutes of constant arguing, the boys finally gave in. Dean had offered to go with her since he'd been to Hell, but Ryder told him he was needed here; besides he spent forty years down there, no way was she going to let him go back. Sam would need him for the case anyway. She was given the knife to help her fight against anything she would come across.

Everyone drove her to an area for taxis, and a full thirty minutes passed before they found a reaper. The conversation had gone down similar to the show. The reaper knew who the Winchesters were, and surprisingly he knew who Ryder and Jenna were. According to him, they were building a reputation, and none of them knew if that was a good thing.

Before the reaper would take Ryder, she pulled Sam to the side. She kissed him as if it would be their last kiss. Sam didn't know why but he could feel the goodbye in the kiss, and he fought back the tears that wanted to be released.

"You better come back. Our daughter's going to need her mother." Ryder nodded not trusting her words. She turned her attention to Lilith in Jenna's arms.

Lilith reached for her mommy. She could see that her mommy was sad, and wanted her to feel better. Why was she so sad?

Ryder held her, and kissed her forehead. "I'll come back baby." She gave her to Sam, and hugged Dean and Jenna. She walked up to the reaper.

The reaper held out his hand to Ryder which she took. She pulled out the knife, and watched as she was taken to Purgatory. Somewhere she hoped that Dean and Sam would never have to go. The sight before them cleared up, and Ryder recognized it as Purgatory. Her heart was pounding so hard, and she was terrified.

"Okay, you have twenty four hours to do what you have to do and get back to this spot. If you're not here in that time, I'm gone." He pulled out a watch and gave it to her. He pointed to a direction in front of her, "Walk that way, and you'll come across a tree with a boulder in front of it. That's your way into Hell." With nothing else to say, he vanished.

Ryder put the watch on her wrist, and started walking mumbling about no one knowing how to say goodbye anymore.

Dean and Sam walked into the room followed by Pamela. Jenna looked up from feeding Lilith.

"You know this has to be a very stupid plan. You do realize that, right?" she asked sitting on the bed.

Dean rolled his eyes. "Yes, we know but we need to do it."

Pamela scoffs. "And which of you dumbasses came up with astral projection?" She looked at them waiting for one to fess up. When Dean raised his hand, "Of course."

Jenna may have been hanging out with Ryder too much, because she felt like she was picking up on her anger. Watching Pamela talk down at the boys especially her husband was seriously pissing her off. She bit her tongue, because she knew the boys needed her.

"This is crazy. Even more crazy since you two idiots don't know what you're doing."

Dean was really getting pissed off. "No, but you do."

"Yeah, I do. Guess what? I'm sick of being hauled back into your angel-demon crap." Dean gives her a look, and after a moment she gives in.

The boys laid on the beds, and as soon as she said the spell, the boys saw that they were in the spirit world.

Just before the boys left to go find the reapers, Jenna spoke out. "Dean, don't even think about feeling up Demi Moore."

Even though Dean and Sam knew she couldn't see them, it was still weird that Dean was just about to say that. Oh well.

Ryder walked carefully but quickly. Thinking about actually being in Purgatory, she realized that the Leviathans were still here. Castiel hadn't taken them yet. Dammit.

She checked her watch; she had been walking for four hours now. She kept thinking that maybe she went the wrong way. She caught sight of a few monster in front of her, and she wasn't in the mood for fighting, so she hid behind a tree. When they were far enough, she looked around for any more. Nothing. Ryder stepped out and saw the tree, finally!

She ran up to the tree and struggled to move the huge rock. "Oh my god, freaking Supernatural!" She pushed harder. "They make this look so easy." The rock finally toppled over, and she had to bend over to catch her breath.

She looked into the hole, and took a deep breath, and she was pulled in. Once inside, Ryder looked around, no one. She remembered what Sam did, but she needed the watch. She had to use something. That's it! She stuffed the knife into her waistband and pulled off her bandana. She tied it around a nail that was sticking out of the wall. It wouldn't stand out to alert anyone, but just enough for her to see it.

Ryder pulled out the knife, and began to walk. How would she be able to tell who was innocent, and who wasn't? The more she walked, the more sick she was becoming. The show seriously did not do this place justice. The place looked even more graphic than the show made it out to be. Blood was all over the walls and floors. The smell was disgusting, and the those few who were chained up to the wall looked beyond tortured. Even with Heaven the way it was, she would picked that over this any day.

She walked down hall after hall, and she came across so many damaged and guilty souls. No one seemed innocent. She was about to turn down another hall when she came to a cell. She felt drawn to it. She looked around, and walked up to it. She held the knife ready in case they decided to attack. She looked through the bars, and what she saw completely shocked her to her core. Peering closer to the occupant, she gasped.

The occupant turned around, and looked at her completely scared. This had to be trick, right?


Dean and Sam walked around watching people go about their daily lives never knowing that there were two ghosts walking around close by.

They came across Cole Griffith's home, and went inside. Convincing the boy that he was a ghost went a lot easier than they thought it would be. Sam felt really bad for the kid seeing his mother crying but could never speak to her. Must be lonely. Being close to someone you love yet could never be with them again.

Cole explained to them about the reaper that came for him, and all of a sudden they all see a reaper enter the home and head upstairs. As they walk up to the bottom of the steps they see a woman come downstairs. Realizing that Dean didn't recognize her, she leaned up to him closing the distance between them and kissed him. Dean may have liked that at one point, but now that he was married, he felt a little guilty. He hoped that Jenna wouldn't be too angry with him.

When they broke apart, Dean remembered who she was and instantly tensed up. "Tessa."

"You guys know each other?" asked Sam who was incredibly confused.

Dean explained the incident at the hospital a couple years ago when their dad died. He didn't really like thinking about that, because for one he almost died, and another it was a reminder of what his dad did for him.

It took awhile convincing Tessa not to take the kid, at least not yet. She wasn't all to interested in the affairs of hunters. All she wanted to do was do her job by trying to get the kid to come with her, and move on to the next person. She hated it when something got in the way of her job.

Cole wasn't to happy with being told that it wouldn't be a good idea for him to stay, and ran up to his room. Sam offered to go talk to him leaving Dean and Tessa downstairs.

"Heard you got married. Congratulations." said Tessa. Hearing her say that, it almost sounded like she actually meant it. Dean wasn't fooled.

Nonetheless. "Thanks."

"What's her name?" Tessa didn't really care about any of that, she just didn't like the awkward silence.


Sam comes back downstairs with Cole, and he has the kid tell Dean and Tessa about the black smoke that was at his funeral. Deciding that it was demons, the door burst open and the black smoke came in surrounding everyone. When it left, Tessa was gone.

Learning how to do what ghosts did was a lot harder than it looked. Cole didn't waste time making fun of them, taking every opportunity to show off. As soon as they got the basics down, the boys set off to the location the demons were.

Pamela sits at the table watching the TV, not bothering to start up a conversation with Jenna, which Jenna wasn't too angry about. Watching her on the show and being with her in person, she could see the difference. She was more of a bitch.

Jenna sat at the bed with Lilith, and out of nowhere both women hear a creaking noise somewhere in the room. Pamela quickly gets up, and Jenna holds onto Lilith not wanting her to be left alone. If she did that and Ryder ever found out, she would never hear the end of it.

Not seeing anything, both women relaxed. Not even realizing that a demon in the veil was already in the room.

Ryder stood there staring at Jessica feeling both very pissed and sad. Here she was with this woman's old boyfriend, and she was in Hell this whole time. That's not right! She was supposed to be in Heaven, not here. She sighed. Ryder opened the door, but not before making sure that there weren't any demons around to stop her.

She closed the door leaving it open enough not get locked in. Jessica watched as a woman walked up to her, and she pressed herself up against the wall. She had enough of people coming in here and torturing her. She just wanted it to stop.

"Jessica?" Ryder said gently. She could see the pure terror in the woman's eyes. "My name is Ryder, and I'm here to help you." She didn't want to scare the woman anymore than she already was.

Jessica shook her head, and slumped in the corner trying to make herself look small. She was so tired of hearing the demons come in here pretending to save her, and then having it ripped away from her.

Ryder bent down in front of the woman. She checked her watch, she groaned. She was running out time. Wandering around the halls trying to find someone to save took a lot of time. She had about eight hours to get back.

"I know Sam Winchester." Hearing Sam's name, Jessica looked up at her. She missed him so much, and wished that she could see again, and not the Sam Winchester the demons posed as.

Seeing the hint of happiness at the mention of her husband's name in her eyes, Ryder breathed a sigh of relief. "You don't belong here, and I'm here to take you to where you do belong." She stood up and held out her hand for Jessica to take.

Jessica looked at the offered hand, and she so desperately wanted to believe that what the woman said was true. She had been here for so long, and all she wanted was for the pain to end. She thought about it and came to the conclusion that even if she wasn't telling the truth and that it was all a lie, she wouldn't have anything to lose. She smiled and took her hand. She saw the woman smile at her and for the first time in so long, she felt something she thought she would never feel again: hope.

The demon came out of nowhere, and Pamela quickly runs to Sam. "...vis vis vis." The demon grabs her, and she kicks him getting out of his grip.

Although she wants to help Pamela, her top priority was Lilith. She runs to the bathroom and hides her in the bathtub. She checks the window to make sure the salt is in place. She closed the door, and poured salt in front of the door. She turned around and as she did the demon stabbed Pamela. She runs to her side helping her lay on the bed.

Sam wakes up and then exorcises the demon. He didn't really think about the fact that he promised that he was done with his powers to Ryder. Hopefully she'd understand that this was important.

Dean and Tessa went back to Cole's house. They both walk up to him and watch as he looked at his mother. The atmosphere in the room shifts; you can feel the sadness in the air. All Dean wanted at that moment was to go back to his brother and wife. He doesn't want to be there, because he knew what was to come.

Cole heard them behind him, and is so sad. He doesn't like seeing his mother upset. It pains him to constantly watch her cry. In a way, he wants to move on, but he doesn't want to leave his mother. What if she needed him? He turned to look at Dean and the Reaper.

"Tell your brother thanks...for nothing." He said miserably. He feels stupid for thinking that he could stay here with his mom.

Dean looks away in shame remembering what his brother said to the kid to get him to help them. It's even worse when he knows what would happen if the kid were to stay.

Tessa looks at Dean and feels a little bad that he's being talked down at for what his brother had to do. She sighs.

"Cole, look at your mother." He does, and frowns. "Do you see how unhappy she is? As long as she can feel you, she'll feel pain. She'll always be unhappy because she can't let go." Cole looks back at her.

Dean steps up. "You need to let her go, so both you and your mom can move on. You don't belong here anymore," Dean said sadly.

Deep down Cole knew they were right. Even though he loves his mom, he feels sad. Not that he died, of course he felt sad about that, but it was something else that he didn't know.

"What'll happen?"

Ryder and Jessica walked down the same path she came from. No one spoke, because no one knew what to say. What do you say to your husband's old girlfriend who has spent four years in Hell? What do you say to a stranger who came out of nowhere wanting to rescue you?

Recognizing the area, Ryder knew that they were getting close to the exit. Her blood was pumping, and all she wanted to do was get out of there. Not a place she wanted to be any longer than necessary, especially since she was still alive. She pointed to the exit, and Jessica was so full of hope that she was getting out, all she thought about was running to get the hell out of there.

Both were so focused on getting out, neither noticed two demons creeping up on them. Ryder noticed them too late, and was shoved up against the wall. She fell to the floor, and saw the other demon grab Jessica. She realized that Ruby's knife wasn't in her hand anymore, and saw it across the floor near the demon holding Jessica. Maybe that guy was right, maybe they should start putting their weapons on bungees.

The demon that shoved her, went to kick her, but she moved just in time. She rose to her feet quickly, and dove for the knife and stabbed the demon just in the nick of time. Killing the first demon was easy, trying to kill the demon that had his grip on Jessica was going to be a little tougher.

"Let her go!" She yelled holding the knife in a defensive posture. She didn't have time for this. They needed to get going.

The demon smirked. He didn't say anything only just backed up, pulling Jessica with him. Jessica was really terrified. She had spent so many years being tortured by these demons, and she was so close to getting out. She was already dead, and there was no way she was going to let the other woman get hurt because of her.

Jessica shook her head. "It's okay, go. Thank you for trying but it's not worth it." She was fighting back the tears that wanted freedom.

Ryder scoffed. What is up with the people in this show being so self sacrificing? "I'm not leaving without you." She turned to look at the demon.

"Listen to her. Walk away if you know what's good for you." He spat out.

"If you're so sure you can win, why don't you fight someone who can actually fight back? Or are you too chicken shit to fight?"

The demon threw Jessica to the floor. He stood in front of Ryder and the fight broke out. Well it wasn't much of a fight, the demon didn't know what he was doing. He got too cocky and that was his downfall. Ryder stabbed him in the chest. As soon as she killed him, a loud siren went off.

Ryder helped Jessica up, and they both looked up. "Okay, that wasn't in the show." Ryder said looking around. Jessica looked at her confused.

"Show?" Ryder waved her off.

"Nevermind. We have to go, now!" They ran for the exit, and just as they were pulled out, Ryder grabbed her bandana. They made their way out and began walking.

They walked for about an hour silently. Jessica really wanted answers, and she wasn't going anywhere until she got them. Not that she wasn't grateful for the woman helping her, she just needed to know what was going on. She stopped and crossed her arms.

Ryder looked back at her, "What's wrong?"

"Why did you save me? Who are you?"

Ryder checked her watch. Damn. They only had three more hours. She rubbed her forehead in frustration. "My name is Ryder Winchester, and I'm here to save you because I'm trying to close the gates of Hell forever." No time to beat around the bush.

Whatever Jessica was expecting her to say, that wasn't even close. Something she said caught her attention. "Winchester?"

"Look I'll explain everything, but we need to keep going." Jessica walked with her.

Ryder kept her word, and explained as much as she could leaving out of the show. Jessica was quiet throughout it all. At first it made no sense, but the more she listened the more it made some sense. Hearing about the trials freaked her out, but she had to give the girl some credit.

"So you married Sam?" Jessica was a little jealous, because when she was still alive all she did was imagine herself married to Sam. She loved him so much, but in the end she was glad that he found someone that made him happy. She was afraid that he wouldn't find someone.

"Yes, and it was the best thing I ever did." Ryder felt a little bad that Jessica was going to marry Sam, and here she was talking about her marrying him.

Jessica and Ryder stopped. They heard yelling off in the distance, and when they looked back they saw hundreds of monster running at them. Their hearts began pounding in their chest. Jessica was beyond scared.

Not wanting to waste anytime, Ryder pulled out the knife, cut her arm and had Jessica do the same. They held arms, and just before Ryder said the spell, Jessica looked at her.

"Ryder, I'm glad Sam has you." Ryder smiled a little and looked at the monsters getting that much closer. "Tell Sam, thank you. Despite me dying our time together was the best time of my life. Given the choice, I would've done it all over again." Ryder nodded that she would tell him. "Take care of the man we love." Ryder said the spell, and Jessica's soul went inside Ryder's arm.

Not standing there a moment longer, she ran off. Normally she would've stayed and fought, but there were two problems with that. One, she was running out of time, and two there were way too many. She may be a great fighter, but even she knew she wouldn't be able to take down that many.

Glancing behind her, she could see that she was being chased by vampires, shapeshifters, werewolves, and even some Leviathans. She must really be hated if monsters of different types were ganging up just to kill her. She checked her watch, and saw that she had three minutes left, and she wasn't close to the spot she had to be at, and worst of all she was getting tired.

Still running and her time almost out, she saw the reaper standing there waiting. She looked at her watch and she had twenty seconds left and by the looks of it the reaper was getting ready to leave.

"WAIT!" She yelled. The man looked up at her, and he was starting to fade. Checking her watch, she realized she had ten seconds left. She really didn't want to be left here. 8...She couldn't let Jessica down. 6...She had one more trial to do. 4...The monsters were getting closer. 2...She began to cry; she didn't want to die, not like this. Ryder jumped into the reapers arms, and they both fell to the ground. And by the looks of it they were back to the land of the living. Ryder's head slumped to the ground in relief, and the emotions were too much and she let go. The reaper still holding her.

Pamela sits on the edge of Dean's bed, one hand to the stab wound, leaning on the other.

"All we have to do is talk to Tessa and have her hold off on reaping you." Sam said.

Pamela smirks and shakes her head, "I think she's started up again." Sam looks at her confused, and looks at her hand. His eyes widen when he sees blood pouring out.

Dean takes a deep breath and sat up. Jenna moved to his side leaving Lilith on the bed. Dean looked at Pamela, and moved to her side. "What happened?"

Pamela looked around the room, and when her eyes land on Lilith she frowned. That's what that was.

"Pamela, I'm so sorry," mumbles Sam. "You don't deserve this."

"Yeah, you know what, I don't. I told you I didn't want anything to do with this!" Pamela starts coughing up blood. Jenna didn't know what to do. She was hoping that this would have been avoided. She thought about the episode that showed Pamela happy in Heaven. Maybe she was always meant to go.

"If it's any consolation, you're going to a better place," Jenna said.

Pamela looks up at her, "You're a terrible liar, but what the hell, right? Everybody's got to go sometime." Pamela looked at Sam. "Come here." Sam leaned in closer. Pamela whispers," I can feel what's inside of you, Sam. If you think you have good intentions, think again." She coughs again. She leaned back against the headboard, a trickle of blood coming out of her mouth, and is still.


Her head slides down.

"Pamela!" Dean yells. No matter if they didn't know her for very long, he still looked at her as a friend. Why did his friends have to keep dying? Dean looked at Sam, "What did she say to you?"

Sam looks away in shame. It was bad enough that he used his powers, it was worse when he was called on it. Did he really have to tell his wife? He scoffs, of course he did.

Sam, Dean, Jenna, and Lilith went to back to the place they last saw Ryder. As they were walking, Sam saw Ryder sitting against the wall. Sam ran up to her, and he saw that she was sleeping. By the looks of her face, she was badly worn out. He picked her up, and brought her back to the Impala.

Dean drove them back to the motel they stayed at. He looked in the rear view mirror, and saw his brother holding his wife. Whether it was for her comfort or his he didn't know. He felt really bad for her, since he had been to Hell, he could only imagine what she had to go through. He hoped that all the trouble she went to save someone, that she actually did it. He didn't want to think about her having to do all that again.

Pulling into the motel parking lot, Dean and Jenna got out. Jenna knew what her best friend had to do to complete the second trial, and she hated it. All of this, because of her love for the boys.

Ryder could feel the Impala stop, and although she didn't want to wake up she knew she had to. Jessica's soul was still with her. She had planned on releasing her when the reaper left, but she was too tired. Sam helped her out, and was pulling her to their room. Ryder got of his grip.

"You need to rest." Sam reasoned.

"I have to release her soul first." Ryder took out the knife, and cut her arm. It was a good thing no one was around to watch. Everyone gathered around her, and watched as the soul within her arm came out and slowly rose.

"Whose soul is that?" asked Sam still looking.

Everyone was captivated at the beauty of the soul. It was a beautiful ball of energy. "Jessica's." Ryder whispered.

A few tears dropped down Sam's face, and they all watched as her soul went to Heaven.

Ryder didn't care if the brothers heard her say the spell, because right now she just wanted to sleep. She whispered the spell nonetheless, and braced herself for the pain that shot through her arms. She fell to her knees crying out from the pain. It was even worse than the first time and lasted longer.

Sam held her and when she stopped crying out, he looked at her and saw that she passed out. Probably for the best, he thought. He carried her in, and placed her on the bed.

They all fell asleep, and the last thing that went through Ryder's mind was: one more trial.

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