Title: I Wonder if He Knows
Author: Nobdyptclr
Disclaimer: Nope, still not mine
A/N: Just needed to get this out of my head. Sorry for any errors, no beta and a fried brain.
"I wonder if he knows how awkward he was," Sam thought, studying his brother as they drove away from the town. Angela and Lucas were already out of sight, and Dean seemed focused on the road, unaware of his brother's scrutiny. Sam smirked to himself. Imagine, the great womanizer and self-proclaimed chick-magnet getting tongue-tied when a woman kissed him. He almost laughed out loud, and quickly turned to look out the window so Dean wouldn't see his expression. This was a perfect weapon to add to his arsenal – a reminder of the awkward moment would embarrass Dean to no end. As he opened his mouth to start the teasing, a realization came to him, stopping him cold. Dean was always comfortable flirting with women – waitresses, bar tenders, strangers on the street. It was when he faced a single parent with a real life and responsibilities that he lost his ability. When it was fun and games, Dean had all the right lines and answers, but when it could possibly be something more he flinched away.
The smile fell away from Sam's face as he realized how lonely Dean's life must be. His brother didn't lack feminine companionship, but he couldn't ever remember Dean in a relationship that lasted more than a few days. They rarely stayed in one place long enough to form lasting bonds, and when the possibility did arise, Dean tended to shy away from it, claiming that it wasn't worth exposing anyone else to the danger that they faced every day.
Sam frowned and looked over at his brother. Dean had turned the radio up and was tapping his fingers on the steering wheel, oblivious to his little brother's thoughts. Sam made the uncomfortable realization that in the area of relationships his knowledge actually surpassed his big brother's. As he looked at Dean, he thought of Jess, picturing her in his head. For the first time the memory of her wasn't painful, and he felt gratitude for the time they'd had together.
Dean felt his brother's eyes on him and glanced over, concern on his face. "What's wrong, Sammy?"
Sam didn't bother to correct the name as he looked away. "Nothing. I'm fine." He looked out the window again, remembering the good times with Jess. Maybe it really was better to have loved and lost…