Anna doesn’t get to spend a lot of time with her cousins. They live in another state and their school calendars don’t really line up with hers, so the only chance she gets to see them is for a few weeks in the summer. The first few days are always them catching up with each other, then hanging out by going to the pool, or watching movies, or sitting around the TV for hours on end while claiming to be bored but not actually doing anything to change that. You know, typical teenage summer stuff.
It’s during one of those outings to the theater that Anna meets Dean Winchester.
Now, Dean is an especially attractive young man. His face and his arms and those eyes, plus that voice. All of it was made to have girls fall madly in love with him. But still, Anna probably wouldn’t have given him more than a second glance— what’s the point of a long distance relationship when you’re in the tenth grade?— if it weren’t for her cousin Cas.
Cas, who’s normally so quiet and reserved, but who looks at Dean like the guy hung the moon. His eyes sparkle with affection when Dean ditches his friends to come over and say hi. His smile is huge and genuine and ecstatic in a way Anna hasn’t seen since they were little kids opening presents on Christmas morning. And it’s not like Dean seems unaffected either; he blushes when Cas compliments him and seems to find every opportunity possible to crowd into Cas’ space.
Anna’s mission for the next few weeks is clear: get Dean and Cas together.
She tries to be subtle at first. She finds ways for Dean to join them when they do things, then casually disappears to go to the bathroom or make a phone call or something. But the two are so dense that neither takes advantage of the opportunities she presents them with. There are only a few days left before her flight back to Vermont, and damn if she’s leaving without some sort of success. Desperate times call for desperate measures, and Anna goes all out.
Sitting at Castiel’s desk, she grabs some of his stationary and writes the most over the top love confession she can think of, full of poetry and a few pop culture references she thinks Dean will like. Then she carefully signs it, licks the seal, and writes out Dean’s address. Once it’s ready to go, she slips it into her pocket.
“Cas,” she says sweetly as she peeks into the living room. “You wanna walk the dog with me? I wanna mail some postcards to friends back home.”
“Sure,” he answers as he turns off the TV and goes to get his shoes. “There’s a mailbox a few blocks over.”
As they walk, Anna gets Cas talking about school. It’s one of the topics he’ll go on and on about, and she wants him distracted. By the time they stop at he mailbox, Cas is in the middle of going over his college prospects while the dog sniffs the blue box.
“Uh huh.” Anna nods, pulling out some lipstick. “Put this on, please. Tell me about KU’s programs.”
Cas keeps talking, not even pausing long enough to wonder why his cousin just asked him to put on lipstick.
“That sounds like a good place to go to school. Any scholarship opportunities?” Anna asks, taking the lipstick back and holding out the letter to Dean. “Could you kiss this? Right here?”
Again, Cas does as he’s told while answering the question. It isn’t until she’s dropped the letter safely into the mailbox that Castiel frowns. “Why did you have me kiss that letter?”
“Don’t worry about it.” She offers him a tissue to clean off his lips.
Never one to make waves, Castiel shrugs it off and now starts asking Anna if she’s made any plans for college yet as they continue their walk through the neighborhood. For the next few days, Anna’s on edge, wondering if and when anything with Dean will happen. With her flight coming up, she just prays she gets to see it happen before she leaves.
As if to grant her wish, the day before she’s set to leave, the doorbell rings. Anna thinks nothing of it - they ordered Chinese food, after all - so she stays where she is and lets Cas get the door. It takes longer than it should, so Anna decides to go investigate and offer to help carry everything.
“You really didn’t write this?”
Oh shit! Anna sneaks closer, staying out of sight and doing her best not to be heard.
There’s an awkward silence.
“I didn’t write it,” Castiel says, “but I agree with everything that’s there. Your eyes are breathtaking, and I am entranced by your unending kindness, your loyalty and even the protective way you look out for Sam is incredibly endearing.”
Anna’s going to have to tease her cousin about that, because that’s just too sappy.
“… Yeah? Cuz I was really excited when I got this letter, and it was a huge disappointment to find out you didn’t write it?”
“Would it make you feel better if I sent you another one? One I actually wrote?”
“I would definitely like that.”
Anna tiptoes away, not wanting to eavesdrop on them kissing or being any more lovey-dovey because she can’t handle that. But still, she is very proud of her handiwork and fully expects Cas to make her maid of honor at their wedding.
(Spoiler: He does. Anna delights in telling the story of how they got together, and Dean and Cas always indulge her.)
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