Castiel first heard of Valentine's Day via a flyer, freshly printed and stapled to the notice board in the lobby of the motel Sam and Dean were staying in. It was cyan and pink, and punchy printed hearts encircled the caption: Surprise your loved one this Valentine's Day! The line below it read, Sheila's chocolate delights are sure to delight your special someone bargain prices range from $2-$9.50. The address and phone number of the chocolatier were listed in bright text at the bottom of the advertisement. Cas gingerly touched the pink lettering of the flyer, and a bit of the pink letter S rubbed off on his fingertips. The ink and paper smelled like gunmetal, and something else, too... something sharp and hot and indescribable. On a whim, Cas snatched the flyer from the bulletin board, and with a snap and a rush of cold February air, he was standing on the sidewalk in front of the chocolatier. The large front window had SHEILA'S SWEETS painted on in large, white letters, and below it was a cartoon of a cupid. Cas reached out and touched the cupid on the window a much cleaner, cuter-looking version of the cupid he knew. The window was frigid, and the paint of the cartoon and lettering flaked off in places. Cas wanted deeply, for some reason that he didn't know, to go inside. He wanted to get away from the cold eating away at him, try some of the foil-wrapped chocolate on the decorative trays inside the window, and most of all, he wanted to learn more. Valentine's Day. It was special; he knew that much. But it wasn't a holiday for lone wolves, Cas thought; it definitely wasn't for him. If only he had someone... but no. Cas forced himself to tear his thoughts away from the chocolate, the painted display, the pink confetti sprinkling the floor inside. He turned away, head down, and let himself get sucked into the cold.That was Castiel's first Valentine's Day, and it was spent alone.

Another 11 months rolled around, and as pink hearts and chocolates started appearing in store windows again, Castiel started to think again of Valentine's Day. He now knew much more about it than he had the year before. He'd read all of the sappy heart-shaped cards that were put on clearance starting February 15th, and even though they were incredibly cheesy and he had every reason to have aversions to the holiday, he still felt pangs every time he thought about it. Cas was alone, and he was tired of it. He wanted something more, and with one person in particular... He hated to admit, but recently he had been feeling increasingly drawn to Dean. Dean, his friend, who was always there for him. Dean who never gave up, who always was on Cas's side. Dean, with those green eyes, those soft lips that Cas longed to...NO. Cas slapped himself, trying to will away the blush creeping to his cheeks. This wasn't supposed to be happening to him. He was an angel! Strong, independent, keeping a clear head above everything else. Humans were supposed to be the messy ones, the weak ones, always falling over themselves in their simple beauty. Cas had always been the strong one.Cas would have been lying to himself if he said that he hadn't been attracted to Dean all along. Even as he was dragging him from the depths of hell, he sensed the bond between them. It was magnetic, and growing stronger every day. A week later, just a few days before the 14th, Cas found himself yet again in front of a chocolatier's, candy hearts and all. The differences between this one and Sheila's were few instead of a cupid, the window was painted with pink and white hearts, and this one was slightly smaller, the counter a little more shallow than the counter inside Sheila's. But that didn't matter. What mattered was that it was there, and that Cas was standing in front of it, cold and longing to step inside. And that was what he did, quickly and carefully. This was a delicate moment, and he couldn't afford to mess it up.Welcome to Coco's, said the freckly woman standing at the counter. Today's free sample is cheesecake swirl fudge. Can I help you? Cas swallowed, nervously pulling on his tie. What would you recommend for a valentine? The cashier smiled. Well, what does your special girl like?Actually, it's not a... never mind. Cas shook his head, blushing. He quickly grabbed the first thing he could and put it on the counter, head ducked away. He payed in awkward silence, mumbled a thank you to the cashier, and walked back out into the cold.Once he was far away from Coco's not to be seen, he ducked into an alley and pulled the plastic bag with the candy in it from his trench coat. Now he saw clearly what it was: a small, flat box covered in gold leaf. The lid read, Thinking of you, in decorative script. Cas didn't dare open it, but he hoped that, whatever kind of chocolate was inside, Dean would like it. Cas quickly shoved the box back into his coat and walked away into the cold.

On the morning of the 14th, Castiel woke up on the motel couch with his heart pounding. Today was the day... did he stil dare?Yes, he decided, he did. He was ready for this. Cas reached under the cushion for the gold box, his fingers fluttering nervously. Now was the time, while Dean was still asleep and they had the place to themselves Sam had gotten up early to do research on their current case in a nearby coffee shop. Quietly, Cas opened the door of Dean's room, box cradled in his left hand. But Dean was already up, it seemed, bent over an old book at the end of his bed. He looked up and saw Cas standing quietly at the doorway, and Cas knew that it was too late to back out now.Cas? Dean said hoarsley. He looked weary. Cas walked over to Dean's side quietly and sat down besides him. I have something for you, he said. A gift. He handed Dean the small box.Dean put down the book and took the gold box, puzzled, but then Cas saw the meaning dawn on his face. Dean turned to cas, and his eyes softened. Cas, I...Do you like it? Cas asked quietly.Dean nodded slowly, and then, somehow, Cas found himself poised with his face an inch away from Dean's. Slowly, quietly, with Dean's hand finding itself on the back of Cas's neck, they came together.That was Castiel's second Valentine's Day, and his first kiss with Dean. And it was beautiful.