Sam and Caitlin
"There's a part of me that would." Sam nodded. He sighed. "But it's complicated. There's a lot of...factors, I guess." He wasn't sure he wanted to go back to the current timeline. He really didn't want to go back at all. Except he wanted to go back to the life where he and Dean were united, shoulder to shoulder against the world. That very much was not the case in Madison Valley.
Sam knew he'd been distant. He hadn't reached out to Dean for a while. It was awkward, with Dean still living with Sara, after she broke up with Sam. It was easier to avoid them both, even if it wasn't right. Sam sighed, and drew his focus back to the woman in front of him.