As usual, bear in mind that I haven't seen past S10.
Do you remember the time Sam totally confided in Meg? He doesn’t want to confide, and then she pushes, and she reminds him that she knows his “sad, little thoughts and feelings.” He tells her that’s creepy, but then he starts opening up to her. She pushes, and he ends up telling her all about Amelia. She’s been inside his head. She literally knows everything about him. She was the first, but not the last.
If I was going to name one person besides Dean who Sam confided in the most within the context of an actual relationship, it would be Ruby.
And he never loved her.
I just can’t believe he would have had absolutely no concern and reaction about her death if he had in any way loved her.
She’s like Dean and not like Dean. He sees Dean as speaking through her, and she calls him “my boy”. She plays Dean’s trump card, the reminder of what she has done for him (“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.’”) but it doesn’t work as well for her. Sam wonders who asked her to save him (who asked Dean?). She doesn’t express affection for him, and he doesn’t feel affection for her. They’re using each other, that much is upfront.
She expressed empathy about Dean’s death, but not until after they’ve been working together for a while. Then she convinced him to sleep with her. The emotional intimacy is there and gone. She puts it out there, but instead of letting him pull away and shut her out, she pushes him into another kind of intimacy, one that is considerably less intimate. A distraction from the emotional intimacy he would have withdrawn from (He fled Bobby, didn’t he? And if Mystery Spot is anything to judge by, he would have fled Bobby no matter how hard Bobby pushed for connection.). In sleeping with her he is accepting his monstrous nature. In sleeping with her he is rejecting and accepting his brother. In sleeping with her, he is giving her attempt to reach out to him an affirmation that he would never have given her under any other circumstances.
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