You’d known the Winchesters for a long time, and while you loved them both, your feelings for Dean were... different. Sam had caught on ages ago—he wasn’t blind. But Dean? Dean was as oblivious as ever, too busy flirting with every random waitress or girl at a bar to notice the way you looked at him. The three of you were unwinding at a bar after a successful hunt, laughing over lighthearted conversation—until the waitress arrived to take your orders. Dean, ever the charmer, flashed a grin and dropped one of his cheesy lines. Her giggle and the way she leaned closer made your smile fade.

“I need to go to the bathroom,” you mumbled, standing abruptly. You didn’t wait for a response before heading out, slipping outside into the night air.. Back at the table, Dean watched the waitress walk away, a small smirk tugging at his lips. “She’s a knockout, huh?” he remarked to Sam, raising his glass.

Sam shrugged, glancing from the waitress to his brother. “Yeah, sure… but what about Flora?” Dean’s brow furrowed. “What about her?”

“You don’t think she’s even a little attractive?” Sam asked, raising an eyebrow. Dean blinked, caught off guard. “I mean, yeah, of course she is. Why?” Sam chuckled, leaning back in his chair. “Really? That’s all you’ve got? Don’t tell me you’ve never thought about it.”

Dean narrowed his eyes. “What are you talking about?”

“C’mon, man. You’re always joking around with her, you listen to the same music, you’re always in her corner, always protective.” Sam shook his head with a knowing smirk. “Someone who doesn’t care wouldn’t look at her the way you do.”

Dean scoffed, but something in Sam’s words struck a chord. “What way?” he asked quietly. Sam just shrugged again, keeping his expression casual. “You should open your eyes a little. Someone who doesn’t like you wouldn’t look at you the way she does.”

Dean stared at him, the words settling in. He glanced out the window, catching sight of you outside, looking at the sky when a man walked up to you. After a minute Sam and Dean came outside.