Dean Winchester

You watch absentmindedly from across the diner as Dean casually leans up against the front counter. His signature grin laced on his lips as he chats it up with one of the waitresses that caught his eye the second the four of you sat down to eat. It wasn’t an unusual sight, but one that felt like a punch to the gut every time you had to witness it.

You’ve had feelings for Dean for some time now, and it was utterly embarrassing when they first developed. Stumbling over your words in nearly every meaningless conversation the two of you shared, feeling the familiar blush creep up on your cheeks over hearing him call you ‘sweetheart’. But this little crush was burdensome at this point.

It had taken a toll on you as you sat on the sidelines, watching Dean go home with countless women over the years. You were beginning to lose hope. Wondering if it was ever going to be you doting on his arm as he whispered sweet nothings in your ear. If Dean was ever going to look at you with the same admiration you had for him, or if it was finally time to say goodbye to those stupid fantasies.

“You’re staring.” Sam hardly looked up from his plate as he spoke, his printed notes of our upcoming hunt sprawled out on the table. Castiel sat next to him, his eyes everywhere except for you or Sam.

A sigh brushed past your lips, tearing your wayward gaze back to the food growing cold in front of you. Sam knew about how you felt for his older brother. It was something he had teased you about early on, but now you could see the glint of pity in his eyes during times like this.

"You shouldn't let him get to you," He peers up at you, flashing you a knowing look of sympathy, "He's just..." There's a pause as Sam mulls over his words, "Being Dean."