Pie

Every day when Castiel closes his bakery, he sees the same (probably) homeless man (always in dirty looking jeans and a black T-shirt) walk by the window, talking to himself. Cas feels bad for the man and one day he stops the man to give him free coffee and pie. It turns out that the "homeless guy" is Dean Winchester-who is walking to work at his job at the mechanic shop and usually talking to Sam via Bluetooth.

Prompt from a list from Destieldrabblesdaily