"No, the cruelest you ever were to me wasn't then, Ruby. Not by a long shot." It was a bad experience, one that he only wished to re-live again in hopes of being able to save those people. But it wasn't the worst experience that Sam had endured with Ruby because of Ruby. "The worst thing that you ever did to me was lie. This whole time. And then you made me fall in love with you." Sam forced himself to look at her. It was a harder task than he had expected for it to be. "The worst thing you ever did to me was break my heart." Sam didn't say much more about it than that. He didn't want to push it. They were both running on high emotions lately and if he kept on he didn't know what good was possibly able to come of it. Besides, if he knew Ruby, she'd have something to say in response. She usually did. Sam turned his eyes from her once more, this time choosing to stand rather than sit. Sitting wasn't enough. He just couldn't get comfortable around her right now.
"Maybe she did torture you, but that wasn't what you told me had happened." Sam buried his hands in his pockets, emotions all conflicted and riled up on the inside. "I thought you were down there getting yourself ripped to pieces because of what you did for me - because you were one of the good guys. Lilith playing around with you sometimes...now don't get me wrong. It was probably more horrible than anything I could ever imagine. But it's nothing like the picture that you painted in my head." He hated the idea that Ruby had gotten hurt, but at the same time he wasn't much a fan of her having been with Lilith that entire time. Was that her motivation? Do what Lilith says, get outta Hell, find Sam, screw him over, end the world? Maybe it was meant to end the pain. Unfortunately, judging the way that things were between the two of them now, it hadn't. Not by a long shot.
"I am," Sam admitted, turning to face her. "I know it might not mean much to you now that I trashed that moment for you, but I am proud of you. That was a small step in the right direction, Ruby. You keep taking those steps and you'll find yourself getting closer to whatever it is that you're hoping to turn into. Every time you do something like that, simple as it was, you're gonna make me proud. I want you to remember that." It was motivation, maybe. But it was also the truth. He had realized as much after talking to Pike. Small steps, maybe for him, but they were big ones for her. And they always would be.
"I got a gun because my Dad didn't know what else to do about a scared kid," Sam said, shrugging. He wasn't so offended by it anymore. Which was kind of surprising, since the mere thought of the way that his father had raised Dean and himself used to be the most disgusting thing in the world that Sam could imagine. He didn't know how or when, but somewhere down the line his thoughts and feelings on the subject had changed. A lot of things had changed when it came to Sam Winchester's opinion of his father. It was a shame that John would never get to know how much. He looked down at his feet once more, a faint hint of amusement flickering across his face. Big, bad clowns. "Obviously, you've never seen that McDonald's advertisement before. You'd understand my position on this entirely." That said, Sam stepped forward, somewhat hesitantly. He didn't quite rejoin Ruby on the couch, but he did lean against the table beside it as casually as he could. "I think it's going to take some time. We're going to fight, probably. Maybe even over bigger and badder things than what we had to go through these past couple days. But yeah. I think if we both try and we both really just...hang on. We can do this."