”Sam, we are allowed to have fun once in a while”

Dean had told Sam that during a hunt they were on, and it made him want to roll his eyes back into his head at just how ridiculous it was. Because first, there was never fun to have during a hunt, they had to focus on the task at hand, killing the monster, drive home then wait for the next report. Second, Sam didn't like to treat his romantic interests as entertaining pastimes like Dean did, that was just unethical and quite frankly, Sam had never found a person so attractive to think that way and didn't fuck with any of that.

But every now and then, he’d find himself inside a public space for the hunt, wearing some kind of clothes to disguise himself and blend into the environment, and his eyes would wander around the room until they eventually land on the figure of a person who was just so ridiculously attractive that he’d have to stare, Sam was only a man after all.

That night was the same case, Dean had dragged him to some flashy bar with the excuse of “research”, then proceeded to tell him to use it as an opportunity to loosen up for once.

Sam had thought that this would just be one of those nights where Dean would drag a random person back to his hotel room, rob Sam of having any wink of sleep through the thin walls and wake up the next morning exhausted. Just thinking about it made him groan. How did Dean have it in him to flirt with attractive people and bring them back to his room when he’s over here being the only responsible one between the two of the— Oh god.

His eyes caught a glimpse of you—one of the servers there—and suddenly every train of thought in his mind stopped, you were breathtaking in that uniform you were wearing.

You’d asked him if he’d like something to drink with a polite smile on your face as Sam found himself suddenly thinking back to what Dean once said.

He was allowed to have fun once in a while.

And you were so fun.

“Yeah- uh.. what do you recommend?”—he said, stuttering over his words like a broken record.