Oh yes, definitely! Sam is stuck with a brother who loves to flirt, there’s no question. This should show up in the future, once I get a good flirting setup (being ace, I’m not the best at the flirt, that’s for sure).
Sam would be stuck in there, grumbling the entire time. He can only do so much from a pocket if there’s a girl around Dean, after all. Can’t let her figure out he’s got a pint-sized brother squirreled away after all.
I might not have done any flirting (yet!), but a buddy of mine, neonthebright, actually wrote a fic based on Brothers Apart, and here’s a little passage of Sam stuck with his flirtatious brother:
The girl at the front desk didn’t look to be any older than Dean. That was a stroke of good luck. He put on his most winning smile and sauntered up to the desk, leaning an elbow on it casually. “Hey there, miss,” he greeted her amicably. In his pocket, Sam put his hand over his face with a sigh. You’re here to work, not flirt, Dean, he thought, though he knew he would probably never talk that habit out of his brother.
She smiled slowly, the look of someone caught off guard. His smile had definitely disarmed her. Still got it, Dean thought. “Hello, sir. How can I help you? Are you here to visit someone, or are you a new volunteer?” She almost sounded hopeful.
“Visiting,” Dean answered. “I’m looking for Belinda Walters. Can ya tell me where her room is?”
If you want to read more, check out the fic! It takes place right after the First Interlude:
AO3 Fanfiction Deviantart