Six months earlier...
As Sam drove Angels Trans-Am, Ruby grinned at him from the passenger seat, "You know what sounds good? French fries. I'm starvin'. I just escaped Hell. I deserve a treat." At his silence she glared, "You know, a 'thank you' would be nice."
"Who asked for your help?"
"You have no idea what I've been through. When Lilith gets pissed, she gets creative. You want to hear about the corners of Hell I've seen, Sam?"
"No." His hands tightened on the wheel as his sister's face flashed in his head, "I don't."
"And the things I had to do to convince her I was sorry? That I could be trusted?"
"Well, this will definitely get you a fat Christmas bonus."
"Very funny. I'm a fugitive... For you, Sam. I took all of this risk to get back to you, so, yeah, I deserve a damn 'thank you.'"
"Who asked you to save me?"
"I'm just trying to help."
"Can you help me save Angel?"
"No." She eyed him, "Nothing I know of is powerful enough to do that."
Sam glared as he quickly pulled the car over, "Then I have no use for you."
"What?"
"Get out."
"Sam-"
He scoffed, turning to study her, "Whose body are you riding, Ruby?"
"What do you care?" She narrowed her eyes, "You've never asked me that before."
"I'm asking now."
After a thick stretch of silence she shrugged, "Some secretary."
"Let her go."
"Sam-"
His eyes never left hers, "Or I send you right back to Hell."
Later that night, at a hospital...
A woman laid in a coma on a hospital bed with the name 'Doe, Jane' on it.
"Alright." The doctor nodded to his nurse, "Pull it."
After the nurse pulled the plug the machines that were still attached to her began to beep rapidly as the woman died. Suddenly she sat up and gasped in a breath when Ruby entered her body.
Ruby looked between their shocked faces, "Who do I have to kill to get some French fries around here?"
Inside an abandoned house...
Sam, still looking run down, sat at a table quietly cleaning Angel's AE. He was momentarily distracted by someone knocking on the door. Grabbing the shotgun, he slowly opened the door to reveal Ruby in her new body.
"Proof." She held up a piece of paper, "This body is 100% socially conscious. I recycle. Al Gore would be proud."
Sam studied the paper as she walked in, "You grabbed a coma patient?"
"You didn't want me to take a body with someone in it, and I made sure that the spirit was gone. Apartment was empty. You happy?"
Sam followed her through the house, "Why are you here?"
"I can't bring Angel back. But I can get you something else that you want."
"Huh, and, uh..." He looked at her boredly as he put the shotgun back on the table, "What's that?"
"Lilith."
Sam studied her and he knew exactly what she wanted him to do, "You want me to use my psychic whatever."
"Look, I know that it spooks you-"
"Skip the speech." He interrupted quickly, the chance at killing Lilith and getting revenge for his dead sister too much to pass up, "I'm ready. Let's go."
She gaped at him, not expecting him to agree so quickly, "Slow down there, cowboy."
"Just tell me what I have to do."
"Look, Lilith is one scary bitch." Ruby sat at the table, grabbing the open whiskey bottle and taking a drink, "When I was in the Pit, there was talk. She's cooking up something big. Apocalyptic big."
"So let's kill her."
"You want to go in there and half-ass it like before? We have the time to get it right. Let's get it right."
"Okay." He rolled his eyes as he finished off a different bottle of liquor he had, "What do you want from me?"
"Well, a little patience..." She motioned to the scattered beer and liquor bottles around, "And sobriety. Promise me that and I will teach you everything I know."
Back in the present...
Dean and Angel both sat quietly at the table as Sam recounted everything. Angel's eyes were glued to her clenched together hands as Dean stared at their little brother.
"So?" Dean pressed, "What'd she teach you?
Sam shook his head lightly, "Well, the first thing I learned..." He scoffed, "I'm a crappy student."
Six months earlier...
Sam tried exorcising a demon he and Ruby had tied to a chair under a devils trap, but couldn't. Very little black smoke came out of the demon's mouth. As fast as it was out it went right back in. Sam gripped his head in pain as the demon laughed.
Ruby quickly killed him with her knife, "Not funny."
After burying the body, they found themselves back in the abandoned house. Ruby studied the hunter as he popped a bunch of aspirin.
"Just give it time, Sam. It'll get better."
"What?" He turned around chuckling humourlessly before downing the pills with whiskey, "I need more practice?"
"I'm not talking about pulling demons. I know losing Angel was-"
"Hey!" Sam growled, holding up a finger and dismissing whatever she planned to say, "I don't want to talk about it." An angry scoff left him, "You know what? Where do you get off slapping me with that greeting-card, time-heals crap? What the hell do you know?"
"I used to be human. And I still remember what it feels like to lose someone." She shuffled closer to him to put a gentle hand on his shoulder, "I'm sorry."
"Don't." He brushed her off, "I can't."
"Sam, you're not alone."
Leaning down she quickly took him in for a passionate kiss before he could pull away from her. After a second thought thats exactly what he did. Standing, he walked away to put distance between them as he wiped his face.
"What the hell are you doing?"
"Sam, it's okay!"
"No!" He angrily sat on the dingy couch, "That is anything but okay!"
She frowned, "What's wrong?"
"What's wrong?" He scoffed, "Where do I start?"
"Is it because of the body?" As she walked over to him she shed her jacket before dropping between his legs, "Because I told you. It's all me inside of here." She grabbed his hands and put them under her shirt so he was touching her, "There is no one else. And it's nice inside this body, Sam. Soft and warm."
Sam took a deep breath, closing his eyes, but didn't pull away, "What are you doing?"
"Isn't it 'cause you're really scared to go there with a demon? Because it's wrong and it's bad and we shouldn't?"
Sam looked pained for a second as he strained to keep restraint. He broke that restraint a few seconds later and grabbed her hair to kiss her hard. Eventually the two of them were tearing the clothes off one another.
Back in the present...
"Okay, okay, okay." Angel grimaced and flung her hands up to stop him from talking, "We get it, Sam."
Dean held the same shocked and disgusted look, "Too much information, man."
"Hey, I told you guys I was coming clean."
"Yeah, but now I feel dirty." Dean looked over to Angel who was still staring at Sam with wide shocked eyes, "You feel dirty?"
"Like I need to scrub the first eight layers of skin off." She leaned forward, "So what we got is, aside from your gross brain-stabbing extracurriculars with a demon, a manipulative manipulative bitch who seduced you, played mind games and pulled out every stop in the Evil Bitch Handbook to get you to go full on Vader."
"Yeah, well..." Sam frowned, "There's more to the story."
"Just..." Dean motioned forward, "Skip the nudity, please."
"Pretty soon after... that, um..." He cleared his throat, "I put together some signs, omens."
"Saying what?"
"Lilith was in town." The two eldests eyes pierced Sams, "And I wanted to strike her first."
Five months earlier...
As Sam put his coat on and readied himself to leave, Ruby tried to stop him, "You're not ready yet."
"It's now or never."
"No, we got to wait until you get it right." She shook her head, "You haven't been too successful."
"Alright." He grabbed the knife from his bag, "I'll use this."
"Stop." She grabbed his hand, "You can't just fly in there reckless, Sam. We need you to take the bitch out."
"Oh..." He smiled, "I'll take her out all right."
"You get one shot, and you're it." She let him go, studying him, "You're the only one who can do it, Sam. So if she kills you first..." At his tense eyeroll she trailed off, glowering at him, as realization hit her, "You don't want to survive this."
He rolled his eyes, "Come on."
"It's a kamikaze attack. You want to die fighting Lilith."
"That's stupid."
"No, it's the truth." She ran after him when he walked away, "Because if you kill her and you survive this, then you have to go on without your sister!" She moved to block the front door, "This isn't what Angel would've wanted. This isn't what she died for."
Sam's jaw tensed, "Get out of my way."
"No, Sam. This is suicide!"
She grunted when he pinned her up against the wall and pressed the knife up against her throat. Giving her one last look of warning he walked out the door.