It was never really smooth sailing, though. That was the problem. Not for Dean. It was much easier to have one-night stands with his life being what it was. He had almost no idea how Lisa had put up with him as long as she did.
He would've made a move then, too, right then... but Jo deserved better than that. Dean wasn't drunk--yet--but he was getting there fast. He'd like to at least remember sleeping with her for the first time.
He nodded. "I wonder if I ask that demon nicely if he'd just... go away. For a few days," he joked.