Dean had finally succeeded in dragging Castiel shopping. Ever since the angel had fallen, Dean wanted to get him out of the house, even for an hour, especially since the clothes Cas had come with were getting really ratty. They walked into the Macy's in Kansas City and while Cas was looking at all the clothes, Dean found himself distracted by a 40s style fedora.
After Cas found some clothes he found appealing, he headed back to find Dean. Dean was trying on a fedora, and Cas walked up to him and asked, "Dean, could I try on the fedora?"
"No, Cas."
"Please, Dean, can I try on the hat?" Cas pleads slightly, with the help of his puppy dog eyes.
"Dammit, no, Cas." Dean was finding it hard to resist at this point, there was something about those blue eyes that made it hard to say no to the fallen angel. He took the hat off his head, with the intent of putting it back, but seeing how Cas followed it with his gaze, he twisted it around him a while, messing with Cas. Finally, he caved. "Goddamn it, Cas. You're too damn cute. You can have the hat." He put the hat on Cas's head, laughing.
Once he had the hat, Cas started skipping slightly, acting like a child in a candy store. For the first time since he'd fallen, he was genuinely smiling and laughing.