It looks like Dean is still messing with the magic doll, and perhaps those pin pricks are causing someone harm. Or maybe Rowena is behind it all, and Dean just realized they never should have teamed up with her.
Look, was it nice to drop our baggage? Yeah, maybe. Hell, probably. But it wasn't just the crap that got lost. I mean, it was everything. It was us, it was what we do, you know? All of it. So, that's what being happy looks like? I think I'll pass.