The three of you were in Baby, driving to Oregon on your first case since Sam had gotten his soul back. He didn't remember anything of the past year and a half, and had been asking you and Dean questions the whole ride. Which you didn't mind, until he asked Dean a particularly unsavory one.
"Did you go to Lisa's? Have a normal life?"
Sam asks, looking at Dean with wide, expectant eyes. You couldn't help the pang of hurt that coursed through you. That long year had been awful for you, with Dean leaving you out of the blue, having to pick up the pieces of yourself after basically losing both of them, trying to hunt alone and almost dying every other week…it was just bad. And now you and Dean were inseparable again, with him on the cusp of begging you to be his girlfriend. It still stung though. What had almost been permanent.
"Uh…yeah. I was with Lis for a while. Got dragged back into hunting though. I'm not mad about it."
Dean shrugs, looking through the rearview mirror at you to make sure you were okay. He knew it hurt. You'd talked about it to him before.
"Didn't feel right with her, y'know? I just felt like I was pretending to be some other guy."