The very first thought that came to mind was that she’d screwed this up, made it worse by mentioning Jessica. He’d been so eager for the conversation at first and as he’d talked, Ruby had seen the change in him. He was annoyed at her, for mentioning the woman he’d loved before her. For daring to compare them probably. She’d known it had been a mistake to ever do it. To tell him any of this. The avoiding had been going perfectly well until he’d cornered her, and once he had. Once he’d outright told her to tell him what was annoying her, she’d found that as usual he was hard to say no to. Here he was, sitting in front of her, watching her. Probably judging her for being an awful person. For comparing herself to Jessica. He was going to end it, tell her he couldn’t believe she’d been so heartless. Tell her that since it had been Azazel that had killed her that it was her fault too. Every horrible scenario ran through Ruby’s mind wildly, Dean and Bobby helping him end her, or worse still, send her back. Telling him they’d help him through loosing her and he should have known better than to ever love a demon in the first place. None of those scenarios were likely, because she knew Sam did love her, but maybe he was seeing it now. Maybe he was seeing that she truly wasn’t good enough. She never would be.
You’re not Jess. You could never be Jessica
Never going to be near what she was. Ruby heard the words and let out what could only have been a strangled sob as he told her just how superior Jessica Moore was to her. He was going to marry her, he was going to spend his life with her. It wasn’t something she could ever measure up to. And it stung at her in a way that she couldn’t imagine he could understand. So she’d dealt with it by avoidance. Again something she probably wouldn’t have done. She’d have talked it out with him while planning weddings and babies and...Ugh she was a horrible person. She wasn’t even a person, not really, and here she was jealous of a dead girl who had a part of her boyfriend that she couldn’t touch. “I can’t can I, I can’t be that for you. I can’t give you the normal life, the wedding, the kids, the house and career and...” She tilted her head as he spoke, listening to him talk about the freedom he’d had at Stanford, getting away from John. Hiding from the horrible reality for a normal life with Jessica. She noted how tense he was as he spoke and all it did was leave her more confused than anything. What did he mean he didn’t want it?. Of course he did. He’d had it before it was taken away from him. Of course he wanted it. “It’s all you wanted. That’s why you lost it, cause...it didn’t fit the...y’know, the plan. He said you needed to return to what you were. And that’s why I’m horrible...that's why I’m not good enough because that’s why you have me isn’t it. Because that life you wanted got ripped away and I’m...I’m everything you should hate”. He went on to tell her she meant a lot to him, that he didn’t need her to be human, and Ruby, she didn’t get it. Didn’t understand how that was possible because of course he did. Of course he wanted human.
“I know you love me” she said simply. And she did. If nothing else, she knew that. “I love you too”. She might have thought he was settling, thought he was deluding himself, but she knew how he felt about her. He showed her often enough. “You do so much, every day to prove that you love me. But at the same time I wonder if I’m dragging you down y’know. Down into the dark. And you say you’re happier in the dark, But you were happy with her, in the light. How can that change...You were normal. Content. I want you to have everything you deserve Sam.” He really was saying everything she wanted to hear, every single thing to make her remember he loved her, he could feel everything she was and he loved it in spite of the darkness, the past, the fact she’d betrayed him so awfully with her lies. The fact she couldn’t get past her opinion on Azazel. He still loved her with all that.