Cutest Couple

It all started with a prank. An interesting and slightly rude prank. But a prank, nonetheless. However, once Dean Winchester actually meets this prank - a tall, raven-haired senior named Castiel Novak - he doesn't seem to mind. This interesting and slightly rude prank leads to a new club in school, a small fight, a few new friends, and a series of carefully planned dates with the object of this prank, Castiel Novak.

(fanart credit to those who actually did the art)

(possible trigger warning)