[One and only Disclaimer: I do not own HP, SPN or any of their affiliates.]
Bar in Miami
Dean walks in to a quiet bar in Miami. He's giving himself a break - let Sam have some alone time with their Dad. He's twenty years old, he's got a fake ID, and he's got a bottle of SPF 30 in the trunk of the Impala that Sam and Dad are definitely not using further back upstate in Daphne.
The bar is tucked back a little ways off the Miami Strip - an old 1930's joint with smooth sloping corners, faded blue and white from the the sea air exposure. Inside the bar is damp, warm, and a smokey, not quite fruity cigar fug permeates narrow rooms with high ceilings and cement tile floors. The paint is chipped and peeling along the crown moldings that frame a ceiling painted with a night sky and gilt stars, and in the din of the room Dean can barely make out unintelligible cursive in Spanish running around the walls over cracked Havana tile.
The bar is mostly empty - middle of the week October isn't exactly peak tourist season, even in a place that's still a balmy 78F most nights this time of year. At the far end near the wall is a redhead leaning over the counter, thoughtfully swirling her melting ice and lime wedge around in a drained glass.
She's pretty - long red hair, she's wearing an earthy green top and shorts, brown leather sandals, and has a flowery blouse tied around her waist. She has the glow of a soft tan, and a light dusting of freckles on her bare shoulders. When she happens to look up and notice Dean she smiles, and her eyes - bright green that stand out more vividly against the backdrop of her hair and in the smokey atmosphere of the room - crinkle up just so in the corners and Dean knows that he's going to buy this woman a drink.
It's two hours later and Dean's told her the story about the one and only time Sam tried to do laundry at Bobby's - soap suds everywhere, none of it in the washing machine - and she's laughing so hard she's leaning her head against the edge of the bar. She's had her own funny stories to share with Dean, seven years of boarding school in Scotland in a castle begs a story or two - and if that accent isn't sexy he doesn't know what is. Dean's cheeks hurt from grinning. The two of them stand up to leave and the bartender smirks at their backs as the woman asks Dean back to her hotel. Dean's not looking for a serious connection, and neither is she - just a relaxing time with some good company.
Three days later when it's time to drive back up to meet with Sam and Dad, Dean wakes up to an empty bed. No hard feelings - a week on the beach with good company and no expectations was apparently what they both needed. There's a small copper pendant with her namesake embossed on both sides - a Lily, her name is Lily - on top of a folded piece of parchment. Dean smiles as he reads the note, before folding it back up to tuck away in his wallet later. The pendant he ties on to a strip of leather around his wrist that already has a small amulet Bobby gave him two years back. Dean showers, packs up his stuff and moves on with his life.