Every February 14th
What if you met that right person, the one who feels like home, when you were 16?
Dean Winchester moved around a lot. His dad would make him and Sammy pack up and leave every new place after only a few months, so he didn't see any point in trying to make friends. Until he met Castiel Novak. And suddenly everything seemed perfect.
What if you lost that person?
After finally working up the courage to ask Cas out, Dean's dad unintentionally chose then to drag him and Sammy out of their hotel room in the middle of the night, making Dean have to skip out on their date. He didn't even get the chance to call and explain why he didn't show. There was no way the guy didn't hate Dean for standing him up like that.
But what if you somehow managed to find them again?
Ten years later, and Dean still felt like a jerk for what he did to Cas, even if it hadn't been his fault. Every Valentine's Day, he'd feel the weight of his actions and hate himself for it. But then, into the bar where Dean was drinking away his sorrows, walked a familiar guy in a trench coat and dark messy hair, with the bluest eyes that ever existed.
And what if that was all it took?
Time Flies Like An Arrow