Dean was out walking Roxy. He'd managed to sneak out while Sam was asleep, and Che was there to comfort him if he woke up suddenly. With all the to-do about Sam deaging, Roxy hadn't been walked as often, and it reflected in how bouncy and frolicky she was being. Dean waited patiently as she sniffed a streetlight, making sure to get it from every angle.
He noticed a figure coming down the street, still shadowed, and he nodded slightly toward it. Dogs made fast acquaintances.