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Sam stifled the yawn as he unlocked the door. There were advantages to owning your own bookshop, especially when you had the privilege of not needing it for income. Sam and his partner Castiel were both diligent about being open when they said they would be. Their hours were somewhat short – 10 to 6, six days a week – but all their regulars knew that if they wanted to come in, they could call either man and one would be there at any time. Usually, Castiel handled the early morning appointments, but in this case the customer had specifically requested Sam.
That was unusual enough. Even weirder, the customer was Castiel’s older sister Anna. He’d thought Castiel had given her a key, the way he’d given one to Dean, along with the passwords for the computer systems and access to whatever they wanted. Why was Anna so determined that Sam be there for this?
Not that Sam was complaining about the chance to see Anna, of course. He didn’t quite believe Castiel that Anna was the one to insist he be the one to meet her at the store. Castiel, Dean, all of Sam’s friends, even Dean’s girlfriend Lisa and her son Ben, all of them were shipping Sam and Anna hard. Dean had even joked about shoving the two of them into a boat and then blocking the Suez Canal until they got their shit together, he shipped them so much.
Sam wouldn’t deny that he loved Anna, but he didn’t ship it. Anna could do so much better than him. She’d been recently medically retired from the Army and immediately settled into working for a nonprofit advocating for improved tracking and assistance for veterans, particularly those who had lifelong injuries or illnesses related to their service, trying to end the unfortunately high statistic of vets ending up homeless. In the year since her retirement, she’d already made herself indispensable. She was a real-life hero turned angel.
Sam, on the other hand, was a screwup. Ten quarters into his degree at Stanford, he’d ended up walking away to help his brother find their father, ending up in jail for larceny, graverobbing, assault, and the only reason the murder charge hadn’t stuck was because no one could prove whether it was Sam, Dean, or Jake who struck the fatal blow, and since Sam and Dean had been working against Jake, all of them ended up getting off on the technicality. The legal system didn’t exactly take into account that the guy they’d killed was a demon.
While in jail, he and Dean met Castiel, a volunteer who worked with the community college to provide classes for inmates to allow them to pursue education or job skills. Sam signed up for as many as he was allowed to, and when he got out, Castiel had a proposition for him. Despite Dean’s teasing about Castiel having a crush on him, what Castiel really meant was that he wanted Sam to help him run a bookstore. Sam had agreed immediately. Even with the very real chances that the bookstore would struggle and Sam would end up not making much money, it was a good job with a boss he didn’t have to hide his past from and he was explicitly told that one of the perks of the job was that he could order any book he wanted through the store and read on store time as long as he wasn’t ignoring customers who needed help. It certainly didn’t hurt that another perk was that he got to play with the store cats all day.
And then he met Anna. She was one of their first customers, and quickly developed a habit of coming in every day to read for an hour or so. She always bought the book she was reading before she started reading it, so even before he realized she was Castiel’s sister, Sam had no problem with her hanging out. The two of them eventually started talking, and before Sam could realize what was happening and put a stop to it, he’d gone and fallen in love with her.
He didn’t have long to wait for her this morning. She’d asked him to meet her there at sunrise, and just as the sun was coming up, he heard the knock on the door. “Hey. It’s good to see you. What brings you out here so early?”
Anna started to answer, but stopped before she’d gotten out more than a syllable. In her defense, this was because Toni had jumped onto her shoulder to purr at her. Anna grinned and reached a hand up to pet the cat. “Clearly, I came because I missed Toni here too much to stay away until this afternoon,” she joked, earning a huge grin from Sam as he ducked his head. Toni, on the other hand, seemed disgusted with that answer and hopped back down, stalking off with her tail held high.
“I think you offended her.” Sam turned away from watching Toni, noticing Anna’s smile fade a little. “Don’t worry, I’m sure she’ll have forgotten by the time you’ve found your book and come curl up with you like always.”
“I… didn’t come here for a book,” Anna stammered. “If it were a book, I wouldn’t have asked you specifically to be here. I wanted to talk to you, and I’ve been trying to do it for three days, and we keep getting interrupted by customers.”
“Oh. Um. Okay then.” Sam ran a hand through his hair, his mind running away with possibilities. Nothing made sense. She knew his history and why he was working with Castiel instead of following his dreams of becoming a lawyer. She would never interfere with Castiel’s business decisions, even if she thought he was doing a bad job. The idea of her arranging a special meeting to tell him she hated him was just ludicrous. A tiny voice that sounded like Dean tried to convince him that Anna wanted to confess her feelings for him, but that made even less sense. “What’s up?”
“I, uh… Sam, I… Castiel told me I should just tell you this and get it over with, but I’m kind of scared. You’re…” Anna paused as Sam reached out and took her hand, giving it an encouraging squeeze. “I know you’re happy with your life, that you don’t really feel like anything’s missing, but… is there any way you could find room for a girlfriend?”
Sam just stared at Anna. He had to be misunderstanding this. There was no way Anna was suggesting what he thought she was suggesting. Anna pinked up a bit. “Specifically, me, I mean. As your girlfriend. If you give me a chance, I know I can make you happy, make you not regret it, but… please, give me a chance to convince you to fall in love with me.”
No misinterpreting that. Sam burst into shocked laughter. “You brought me here at dawn to ask me to be your boyfriend?”
“I know, asking someone out at work is not good, but the circumstances here are a little different than most. There is no way Castiel would do anything to you for rejecting me, and short of me invading your home, this is where you’re most comfortable.” Anna’s blush deepened. “I’m sorry if I made you uncomfortable, but…”
“No, Anna, that’s not what I’m saying.” Sam reached out, brushing a tendril of red hair back behind Anna’s ear. It got her to look up at him. “I can’t give you a chance to make you fall in love with you, because I already did. That’s what I’m laughing at. I swear, you must be the only person who didn’t know that.”
“Castiel?” Anna whispered. “Dean?”
“Yep, which is probably why Castiel told you to talk to me,” Sam agreed. “Dean’s been trying to get me to talk to you, but I really didn’t think I had a chance with you. I was fine with loving you from afar, treating you as a sister since Castiel has all but adopted me as a brother, but if you really feel the same way, then I can definitely find room in my life for a girlfriend. For you as my girlfriend.” He paused to let that sink in. “May I kiss you?”
“Please.” Anna’s eyes fluttered closed, and Sam bent down to gently press his lips to hers. The kiss was short and sweet, but Sam didn’t want to push it too far. Not yet. “So, normally, this is coffee hour for me. Would you like to join me?”
“I would love that.” Anna slipped her arm through his. “Coffee shop or bring them back here?”
“Here. More private, until it’s time to open anyway, and more reliable wi-fi.” Anna’s giggles were well worth the joke.