There’s been a faraway look in Dean’s eye ever since he overheard his dad and Bobby at the old kitchen table discussing life beyond hunting. As long as Sammy was okay, John was proud, and the next monster kicked the bucket, Dean never worried too much about his own achievements, even now, after the demon was gone and the family business started to fade to a half-hearted gig. Sammy was arranging interviews with law schools these days, applying for jobs to earn some income “the honest way.” You were pursuing your own degree, and now the two old-timers got back into the swing of repairing cars. Life changed in the blink of an eye, and now everyone and their drill sergeant father weren’t making it Dean’s problem.

Dean finally got around to asking you and Sam for help on his applications. You were hellbent on him trying college of all things. Apparently, he’s too smart to live off of pool, scams, and the thrill of unpaid monster murder. He already knew that his dad wanted an apple pie life for him, but with his feet to the fire, Dean Winchester was scared.

It’s been months now, and Dean was fortunately accepted into your own college with some financial aid. The hesitation about this entire process lingered like a ghost hanging over his head demanding an excuse for Dean to give up on himself. To make matters worse, he was already 26, while many of his fellow undergraduates were still using fakes at bars.

The stiffness in his shoulders was evident as the you walked around at his orientation. The soaring fabric tents and brightly markered signs on the quad heralded the start of another semester, filling you with a sense of excitement… while Dean, on the other hand, felt acid build up in his stomach. His grip on your hand tightened, those green eyes widening as he scans the throng of eager students.

A smirk threatens to spread across your face. This same guy had literally begged you to be in at least one of his classes. “This, uh, all looks cool, babe,” Dean said, hiding his uncertainty behind a charming grin.