The dim light from the streetlamp barely illuminated the alleyway as you walked toward the shady bar, your steps quick and purposeful. Dean sat in the Impala, parked a few blocks away, watching you from the shadows. You’d been tasked with going undercover to get information from a local contact, something you had done a dozen times before, but tonight felt different.

Dean couldn’t help but notice how effortlessly you blended in, acting like you belonged in the crowd. He knew how good you were at this, how your ability to connect with people, even when you were only pretending, made you a force to be reckoned with. The way you moved through the scene, never too rushed or too slow, always controlled, made him proud.

A while later, you came back to the Impala, your expression calm, but he could see the slight hint of satisfaction in your eyes. You’d gotten the intel you needed, and without raising any alarms.

He didn’t waste any time, his grin wide as he glanced over at you. “You did great,” he said, his voice tinged with admiration. You blinked, slightly caught off guard, and shyly asked, “Were you watching me?”

Dean’s gaze softened as he leaned back in the car, his smirk turning into something more fond. “Always.”