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The three times Dean asks Cas to marry him, and the one time he says yes. [ao3 link]

                                                   At Nine Years Old

The first time Dean asks Cas to marry him, it’s a Thursday.

They’re sitting on a playground swing set after school, kicking their feet to see who can go the highest. Cas thinks this contest is clearly unfair, because Dean’s not weighed down by an ugly trench coat that Mother makes him wear, even though it’s the middle of August and it’s a balmy eighty-five degrees outside. He’s practically sweating through it, and the exertion from kicking his legs doesn’t make it any easier.

“Can’t catch me, Cas!” Dean squeals from next to him as he arcs upward again, this time almost clearing the top of the swing set. “I’m gonna go allllllll the way over!”

“You can’t!” Cas yells back as he fruitlessly tries to pump his legs harder than before. “It’s impossible!”

“Nuh-uh!” Dean objects with a pout. “Benny says that his brother does it all the time!”

Cas grips the chains of the swing tighter when Dean flies upward, this time cresting above the swing set’s top and arching backwards. When he comes back down, the chains rattle and Dean flies by, mouth turned upward as he kicks his legs again to gain momentum.

“You’re gonna hurt yourself,” Cas calls out, toeing the ground to stop his movement. “Just give it up, Dean.”

“Nope!” Dean cries out when he passes by again.

“I bet you can’t even do it,” Cas mutters under his breath, which Dean catches as he flies by. After arcing up and almost making it over, Dean digs his heels into the grass to stop his ascent. Cas looks over at his friend and finds his lips upturned into a crafty smile, which can only mean one thing.

“You wanna bet?” Dean says as he gets up from the swing and walks in front of Cas.

Cas scoffs at Dean and crosses his arms. No, he doesn’t want to bet, because Dean probably will make it all the way around and Cas’ll be stuck doing his homework for a week, or he’ll have to ask Lisa Braeden if she likes Dean, or something else equally as annoying.

And yet, he can’t pass up an opportunity to prove Dean wrong.

“Fine,” Cas says, lips in a pout. “If you can’t get over in three tries, then you lose and owe me your snack packs for the rest of the week.”

Dean saunters backwards and grins widely, arms thrown out in an open gesture. “Fine, Cas. But if I win, then…,” he pauses for a moment, but then his eyes fly open and he begins jumping up and down. “Oh! Oh! If I win, then you’ve gotta marry me!”

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