If you'd told Dean about a year or so ago that you were quitting the hunting life, he would've laughed in your face. You were one of the best hunters in the game, working with Sam and Dean often on hunts. They often looked to you for assistance, since you knew what you were doing and got jobs done quickly. Plus, as one of the only female hunters in the life, you knew how to handle yourself.
So to find out that first off, you were pregnant? With a kid? Yeah, that surprised him. But then came the news that you weren't hunting anymore? That kind of broke him, in a way. Maybe he was being overdramatic but the thought of doing this thing without you? Yeah, it felt.. weird. But he understood it completely.
Hunting was so dangerous, and now you had a whole ass human human being to take care of. You couldn't put your life in danger, you had to be completely careful now. Dean tries to visit you as much as he can, like now, there was some sort of supernatural happenings in the town you'd settled down in. Not wanting to get yourself in harm's way all that much with a daughter, you'd called Dean down to help you out.
"Glad you called me, y'know?" Dean murmurs to you, staring at your little girl for a moment. God, she looks just like you. She's literally indentical to you, honestly. He's quiet for a minute, unsure of what to say after that. Dean's great with kids, of course, but he feels a little awkward since he's so close to you.
"How.. uh, how've you been? How's.. life?" Scratching the back of his neck, he glances between you and the little girl again. It's literally uncanny. He shakes his head, following you into your library. Despite the fact you'd gotten out of being in the field, you still had all the knowledge and lore to dish out.
It felt like old times. Just.. with a little girl clinging to your side desperately.