How Do You Love Someone

Chapter Sixteen

Chapter Sixteen:

Days passed after the second trial, and Ryder was feeling more and more like shit. She felt so weak, but at the same time she felt that she could keep going. She had to for she had no choice. She had one more trial to do, and then it'll all be over.

Telling Sam what Jessica had said was a little hard for her to say, because she was always a sensitive subject for Sam. When she finally told him, she felt better and happier when she saw the look of pure happiness in his eyes.


"Sam what's wrong?" asked Ryder sitting on the bed in their motel room. Dean hearing that looked up from cleaning his guns. Jenna was in the shower.

Sam shook his head. "I don't understand." He looked her in the eyes. "Why would Jessica be in Hell to begin with? She was a good person, and I would've expected her to be in Heaven when she died."

Ryder wanted to kick herself for not mentioning that. She had asked that very same question, but it had slipped her mind when she passed out. She cleared her throat. "I know why." Dean and Sam looked at her waiting for her to answer. She didn't like the information she was given when she asked that herself. They deserve to know. She took a deep breath.

(Flashback:)

Ryder's head slumped to the ground in relief, and the emotions were too much and she let go. The reaper still holding her. Minutes went by and they were both still laying there, but Ryder was feeling better and stopped crying. The reaper helped her to her feet.

"I must be going now. Stay here and wait for your family to come back." He turned to walk away, when he felt her grab his arm. He looked at her, and she looked so sad.

"What's wrong?" He normally didn't care about the well being of humans, but for some reason he felt genuine concern for this woman. Dammit, I'm going soft, he said to himself.

"Why was she in Hell?" she asked quietly. She was so tired, and all she wanted to do was sleep, but this had been bothering her ever since she saw Jessica in the cell.

The reaper sighed. "Jessica Moore was in Hell, because she knew Sam. Azazel not only had her killed because she was getting in the way of Sam's destiny, but he also made sure she wouldn't be taken to Heaven. It would be the ultimate punishment for Sam for going astray."

Ryder looked at him, "How do you know that?"

He looked away. "Because I'm the one that reaped her." He looked back at her, and he no longer saw sadness in her eyes, but anger.

Ryder yanked her hand back not wanting to touch him. "You took an innocent soul to Hell because of who she knew?!" She didn't wait for an answer, and punched him in the face. Since he wasn't expecting it, he went down. She was breathing hard, and it took all her strength and will power to force down her anger. She wasn't going to let it out. No, I'm in control. It doesn't control me!

He rose to his feet, and walked away. "Good luck Ryder." He called back.

(End Flashback)

Sam felt so terrible. It was bad enough that she was killed because of him, it was even worse to know she was taken to Hell because of him. He wanted to be alone, so he grabbed the car keys and left.

Dean and Ryder watched as he left the room. Dean felt so bad for his brother, and wanted to console him but what do you say to that? How do you comfort someone in this situation?


Time went by, and Jenna was wondering when Ryder would do the third trial. If she really thought about it, the third trial would be a lot easier than the other two. All they had to do was find some demon, and cure it. Easy. So what was she waiting for?

Jenna may be a blonde, but she wasn't stupid. She's been noticing that her and Ryder's relationship hadn't been the same. Not since the siren. Maybe Ryder hasn't forgiven her like she said she did. She really didn't mean any of the things she said. It's not like she could do anything about it now. There were more important things to deal with than their relationship.

Moving on to a new motel, a flutter of wings were heard by the door. They all turned their attention to their visitor. Or in this case visitors. Castiel and Uriel. By the look on their faces, whatever they were going to say wouldn't be good.

"What do you want?" asked Dean very tired.

"We have captured Alastair." answered Castiel like it was enough.

Dean set his bags on the bed, "And?"

"We've come to his student. You happen to be the most qualified interrogator we've got." sneered Uriel.

Dean looked quickly at Castiel. They can't be thinking that, right? No way in hell was he going to do this. "No. No way. You can't ask me to do this, Cas. Not this."

Jenna remembered this, and this wasn't good. Ryder got up from the bed, standing in front of Lilith. She knew this episode, and she wasn't looking forward to this. In her opinion, this episode did so much damage to Dean that is wasn't even funny. This couldn't be happening!

Uriel walked swiftly to Dean, and just before he went to touch him, Ryder stood in front of Dean. "You're not taking him. Either you leave him alone, or your secret gets out."

Uriel was getting really fed up with this woman. He wasn't going to let some whore get in his way. He grabbed her shoulder, and threw her against the wall. As soon as she hit the wall, Uriel, Castiel and Dean were gone.


Jenna was in a full out panic mode. She remembered this episode and it wasn't one of her favorites. This wasn't going to do any good for Dean, and now he's gone! She prayed with all her might that this wouldn't happen, but it did. What good was it to know what would happen if she couldn't use her knowledge to help the man she loved? She had to do something, and she had to do it now!

Sam waited for his wife to come to, and all the while thinking of Dean. He loved his brother, and he thought the world of him, but he couldn't help think that ever since he came back from Hell, he wasn't like how he was before. He seemed more fragile. Sam felt angry with himself for even thinking of it, but he couldn't help but think that Dean wouldn't be able to do it. Dean wasn't the same man he was before, and maybe even a little soft. He hated to say it, but Dean was too weak. He needed help, and Sam could do that, but sadly he needed someone's help for it. Someone he promised he wouldn't see anymore.

Ryder was coming to, but she didn't open her eyes. She needed a moment to herself, and she wouldn't get it if she were to make it known she was awake. Okay, Dean is told to torture Alastair, but Uriel would mess it up. Sam goes to Ruby, drinks blood, and uses his power. She internally growled at the thought of that bitch! She didn't like it, but she also felt angry with Sam. He knows about his promise, but he'll still go. She opened her eyes, with one goal in mind: Get Dean back at any cost!


Sam had left the room saying he was going to the store, and pulled out his phone. Even though he didn't want to, he had to call her.

Jenna was pacing back and forth, thinking of what to do to get her husband back. Everything kept coming back to Castiel. He was getting closer to Dean, so he might be able to help. If she thought about it, he would definetly help if she were to tell him who was killing the angels.

Watching her husband leave the room brought so much disappointment to Ryder, and it hurt her. She loved Sam, she really did, but she was getting very angry with him. At this point, she couldn't stop him from going to Ruby, but she could stop him from interfering. She wasn't going to let him damage whatever self esteem Dean had.

Going back to the episode, Ryder had to take a few a deep breaths to get her anger under control. She didn't want to admit it, but she wasn't going to be able to control it forever. Jenna looked at her friend, and her heart skipped a beat. This was what she feared would happen. Jenna ran to Ryder and embraced her.

"Calm down, Ryder. It's going to be okay. We'll get Dean back." Jenna rubbed her back.

Ryder's body was shaking. "He's calling her," she said through clenched teeth.

"I know, I'm sorry, but we can't do anything about that right now. We need to help Dean."

Ten minutes went by, and Ryder was finally back to herself. Both girls weren't fooled that it went away. In all honesty, it was just a matter of time. They just hoped that it wouldn't happen anytime soon.


Sam came back into the room, and freaked out when he didn't see any of the girls. Did something happen? Were they kidnapped? He ran into the room, and checked the bathroom. Nothing. He looked around, and saw that a few of Jenna's and Ryder's things were gone. He felt like he could breathe again. If those things were gone, then that meant that the girls took them and left. But why? Why would they leave? He sighed. Maybe it was for the best. After all, Ruby was on her way. He wasn't in the mood to deal with Ryder yelling at Ruby.

An hour went by, and any thought of the girls and his daughter went out the window when he heard knocking. He opened it, and in came Ruby.

"Sam, I'm not exactly dying to tangle with angels again." She sat on the bed.

"I need you to find out where they took Dean." Sam wasn't up to wasting any more time. His brother needed him.

"Not sure I see the problem."

"He can't do it."

"Look, I get it. You don't want him going all torture master again."

"No. I mean, he can't do it. He can't get the job done. Something happened to him downstairs, Ruby. He's not what he used to be. He's not strong enough."

"And you are?"

"I will be." Sam ignored his wife's voice in his head telling him to stop.


Ryder carrying Lilith, walked alongside Jenna. She felt bad about not at least leaving a note for Sam, but this was important. If she stayed, she would have gone off at him for calling Ruby, then she probably would have killed her, and that wouldn't be good; at least not yet.

(Flashback:)

Ryder got herself under control. "We can't let it happen.''

Jenna sighed. "I know that, but what are we going to do?"

Without hesitation. "Call Castiel."

"What good is that going to do?"

Ryder would always think of Jenna as a friend, maybe not the best friend she was, but sometimes she really wanted to slap her. "The whole point of Dean torturing Alastair is to know who's killing the angels, right?" Jenna nodded still not getting it. "You know, just because you're a blonde doesn't mean you have to act like the stereotypical blonde." Jenna rolled her eyes. "We already know who's doing it. So, if we tell Castiel, they won't have any need for him."

She got to her feet and, "Castiel? We have information for you." Both girls waited for the angel to appear. "Come on Cas, you know you need this information."

A flutter of wings were heard, and in a blink of an eye Castiel was there. "What do you want?"

Jenna got to her feet. "We have the information you're trying to get Dean to get."

Castiel looked at them trying to determine if they were telling the truth. "What is it?"

Jenna opened her mouth to answer, but Ryder cut her off. "You're not getting anything from us, until you take us to Dean. Now."

Castiel stared at them for a moment, and in the end he nodded. Ryder picked up Lilith, and Castiel took them to Dean.

(End Flashback)


Ryder stood out of the conversation between Jenna and Castiel. This was Jenna's husband, so she would leave her to deal with it.

After hearing the whole thing, Castiel was furious. He remembered what Ryder told him all those months ago, but now it made sense. He told the girls not to stop Dean yet, until he dealt with Uriel. As soon as he left, Jenna ran into the room Dean was in with Alastair. What she saw before her didn't really do much for her; it's not she hadn't seen it before.

Dean, expecting Castiel, didn't turn to look to who came in the room. "What do you want Cas?"

"You're more pretty up close," Alastair said.

Hearing that, Dean turned around. "What the hell are you doing here?"

Jenna didn't answer him, instead looking at the tools Dean was using. Normally she would've felt sick, but she remembered this was the thing that did so much damage to the man she loved. She saw Ruby's knife laying on the table. She turned to look at Alastair and smiled.

She slowly walked up to him pulling away from Dean when he went to stop her. "You're the famous Alastair, right?" He grinned wickedly. "You know, when he was in Hell you hurt him so much." She caressed his face.

"And I enjoyed every minute of it."

She kept the smile on her face. Dean had no idea what the hell she was doing. "Jenna?"

"I'm sure you did. It made me sad every time I watched this on TV." She ignored their looks of confusion. "I told myself that if I was really here, I would kill you myself." Dean looked at the table and it was gone. She pulled out Ruby's knife.

Alastair smirked. "Sorry little girl, but that won't work on me."

Jenna's smiled like it meant nothing. "Maybe at one point, but you're not as strong as you were, are you?" Out of nowhere, she stabbed him in the heart. Orange light flickered throughout his body. "That's for Dean, you bastard." The light diminished, and she dropped the knife. Her smile faded, and she went to hug him which he gladly returned.


Sam came into the building, and he was confused at the lack of activity. He didn't hear or see anything. The warehouse was just empty. Wasn't Dean supposed to be here? Was he hurt?

He saw a door to a room somewhat open. Slowly pushing the door, he walked in. He turned on his flashlight, and seeing nothing but carts of tools and blood, he got a bad feeling. The light in the room went on, and he turned around to who did it. His heart picked up speed, "Ryder."

She crossed her arms. "Hello, Sam."

He didn't like her tone, nor did he like the blank expression she wore. "What are you doing here?"

Ryder walked up to him calmly. "The question is: what are you doing here?" She looked around. "Where's Ruby?" Sam gulped. She sighed. "I hate to do this Sam, but you leave me no choice." Okay, he really didn't like the sound of that.

"What do you mean?"

"You have a choice, it's either her or me." Sam's heart might as well have stopped. Did it really get that bad that it came to this? Was being with Ruby that bad that his wife would come to this decision? "If you choose her, we're done. If you choose me, no more Ruby. If you want help with Lilith, I'll help you. Trust me on this, please!" When he didn't speak, she took that as his answer. She turned to walk away, but stopped when arms wrapped around her.

Sam held her, and whispered in her ear, "I'll always choose you."


The next morning, Sam was taking care of Lilith while Dean and Jenna went to get breakfast. He looked as wife slept, and sighed. He hated that he put her through so much, and she still stayed with him. He didn't deserve her. He would've been broken if Ryder left him, but would it have been better for her if he didn't choose her?

Dean walked in, and put the food on the table. He looked at Ryder sleeping, "She's still not up?"

Sam shook his head, "She was really tired last night."

"Well too bad, food's here." He walked up to the bed, and shook her. "Ryder? Get up, we got breakfast." He shook her again, but she didn't wake. He frowned. "Ryder?" He shook her once more. Nothing. He touched her neck, and confirmed she was still alive. So why wasn't she waking?

Sam looked at Dean waking up Ryder, but something wasn't right. "Dean? What's wrong?"

Dean didn't turn away from her, "She's not waking up." Sam gave Lilith to Jenna, and went to his wife's side.

"Ryder? Baby, wake up." She didn't even stir.

Jenna didn't know what to do as she watched the boys try to wake up her best friend. Cas, something's wrong with Ryder.

A flutter of wings announced Castiel's arrival. "What's wrong?"

"It's Ryder. She's not waking up." Sam answered. "Is there anything you can do?"

Without answering, Castiel touched Ryder's forehead. He looked confused, and after a moment he pulled away. "Strange."

"What? What's wrong?"

"Physically she's fine, but-" He trailed off not knowing how to continue.

"But? But what?" asked Sam.

"It seems Ryder just went to sleep and didn't wake up."


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