A/N: No Cas this chapter, just awkward attempts to talk about feelings. Enjoy.
Disclaimer: Not mine.
Dean shifted in his seat again, still fidgeting with the pen in his hands. He had sighed three times in the past minute, and couldn't keep from glancing over at Bobby every few seconds.
It was starting to get distracting, and Bobby had work to do.
"Well, spit it out," he commanded, fixing Dean with a look that told him he wasn't getting out of the conversation easily.
Dean thought about denying that there was a problem and escaping to his room, but that would leave the issue unresolved for even longer. He couldn't keep ignoring it and hoping for an answer to fall in his lap.
"I need some advice," he said, finally managing to put the pen down and sit still. "There's this... person at school that I like, but they're not the kind of person I usually go for."
Bobby stared at him for a long moment. Dean picked up his soda, tapping nervously at the can.
"You idjit," Bobby said, shaking his head in disbelief. "You got your panties in a bunch over that? Ask the poor boy out! God knows he's waited long enough for it."
Dean choked on his drink. "You knew?"
Bobby shrugged. "Wasn't like you were being subtle about it," he said, shooting Dean a glance that conveyed in great detail just how dim he thought the teen was being. "The two of you are always makin' eyes at each other, and you talk about him all the damn time."
Dean winced a little, only just realising how obvious he had been.
"You're not mad?" He wasn't sure if he could handle it if Bobby hated him for this.
"I'm gonna be mad if you don't put that boy out of his misery and ask him out," Bobby said, huffing in feigned annoyance.
Dean just grinned, hearing the unspoken approval that he hadn't dared to hope for.
"And remember, if you're gonna have sex, don't do it somewhere I'm gonna walk in on you," Bobby added, practically cackling when Dean made disgusted noises and retreated from the office, face redder than Bobby had ever seen it before.