And good God, under starry skies we are lost
And into the breach we got tossed
And the water's coming in fast
And oh my love remind me, what was it that I said?
I can't help but pull the earth around me, to make my bed
And oh my love remind me, what was it that I did?
Did I drink too much?
Am I losing touch?
Did I build this ship to wreck?
-Florence and the Machine
Dean always entered every giveaway he saw. Even for stuff he didn’t want. A fake name and his phone number in a jar by the cash register, an online entry form, it didn’t matter. He liked the gamble, the possibility, even if the best thing he’d ever gotten was a set of kitchen knives, some of which had been repurposed into hunting weapons. Which is how he found himself here, begging his brother to be his plus-one on a holiday cruise that seemed too good to be true.
“You said you’d go with me!”
Sam looked up from his laptop, staring at Dean with mild annoyance from his position on the bed. He gestured to his foot, wrapped with an ice pack and propped up on pillows. “That was before my ankle fell through the floor of a building. Sorry if I don’t enjoy the idea of navigating a cruise ship hobbling around and in pain.”
“Christmas in the Caribbean, Sammy! What could be more restful than that?”
Dean felt desperation sinking in. “Ship leaves tomorrow, man.”
“So take Jack with you. I’m sure that would be a learning experience.”
“Absolutely not,” Dean said. “I’d look like some kind of creepy sugar daddy. And I’m not spending my vacation babysitting the kid.”
Sam sighed. “What about Cas?”
“Ha ha, very funny.”
“What’s funny?” asked Cas from the doorway.
Dean jumped. “What have I said about sneaking up like that?”
Cas rolled his eyes. “Good for vampires, bad for Winchesters.”
“Remember that cruise we told you about, Cas?” Sam said, a smug grin on his face as Dean's protest died on arrival. “Well, after what happened last night, I can’t really go. So Dean has an extra ticket. You interested?”
Cas nodded. “A cruise sounds enjoyable.”
Dean rubbed his forehead with exasperation. “It’s a couples cruise, buddy.”
“Then why did you want to take Sam?”
Dean didn’t really have a good answer to that. “I’d.... I’d hate to miss our trademark Winchester Christmas.”
“Beer and bad TV movies?” Sam laughed. “We can do that any time, Dean. Go on the cruise. Take pictures so I can live vicariously.”
He looked between Sam and Cas, helplessly outvoted. “I thought...Sam and I would just board the ship, pretending to be a couple, but I’d actually spend six days scoring with desperate housewives and cute activities directors.”
Cas squinted at him. “I’m not sure I enjoy the ethical implications of you inserting yourself into broken marriages, but there’s no reason the two of us couldn’t board together and then separate.”
Dean took a deep breath, then slowly nodded. “Sure. That could work.”