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Once Upon Another Time - Sara Bareilles

He’s driving. He doesn’t know where yet–they haven’t had a lead in a while–he just doesn’t want to stop. The hum of his baby is soothing and as he looks to the passenger side to see Sammy sound asleep, he feels more at peace than he’s ever been.

It’s a strange feeling for Dean, peace. He’s been on the run for most of his life, afraid of looking back but worried about what’s to come. For Sam, mostly. He never stops worrying about Sam now. Even in his momentary serenity, there is still something nagging at the back of his mind. He often wonders what things would be like if he never stopped by Stanford to pick up his baby brother to help him find their dad. He wonders if maybe Sam would have been able to save Jessica. He wonders if they’d be happily married by now. He wonders if he would have been invited to the wedding. The guilt begins to push away his peace.

He’s tried his whole life to keep his family together and yet they all disappear. They all leave him. His mother, his father, Bobby and even Sammy at one point. And Ben and Lisa. The closest thing he had to a normal family life. And just being around him put them in danger. Because family is his greatest weakness. And the monsters and demons and angels know this all too well.

So he drives, his baby perfectly content to be cruising on the blacktop. And what makes her happy makes him happy.