Dean was not the one to do grand romantic gestures. He just wasn't raised that way. He was horrible at expressing how he felt verbally and always called moments when things would get emotional - chick flick moments - and was generally the worst boyfriend ever. Or at least that was his opinion.

That's why when he and Castiel had made it to their third anniversary with only one major blow up which had resulted in Cas leaving - Dean admits this was completely his fault, even though he wouldn't admit how much it killed him - Dean was surprised. He was even more surprised when his boyfriend topped off that night with a rooftop proposal.

As much as Dean hated a part of himself for admitting it, that proposal was perfect. They went to Castiel's family home in Illinois for Christmas this year since they had spent the previous two years at the Winchester's small home in Kansas. Their first night was full of laughter and good natured teasing from Cas' twin, Jimmy, and older brother's Michael, Luc, and Gabriel. There were games that were, what Cas says, wildly inappropriate to be playing with his fourteen year old niece, Claire, but Dean knows that truthfully he was embarrassed that she had better answers to Cards Against Humanity. There was a ton of food to enjoy as well, since Castiel's mother was used to cooking for a small army. When everyone finally had their fill and wandered off to their perspective sleeping quarters, Cas took Dean out onto the roof.

They sat there huddled under the heavy quilt, sharing slow and soft kisses, Cas telling Dean about growing up in the house with four older brothers - Jimmy was three minutes older than Cas - and a baby sister who was like his own personal baby doll. Dean would smile and stare at Cas, delighting in the way his bright blue eyes would dance with delight at a memory. The way the corner of his lip would curl upwards as he chuckled. Everything about this man beside him, Dean loved, craved, and knew he couldn't live without.

Often times Castiel had this very annoying habit of reading Dean so well that sometimes Dean swore he could read Dean's mind. That night was one of them, as all of the things he was just thinking, Cas voiced in his gruff, whiskey laced voice, asking Dean to spend the rest of his life with him.

Of course nothing was ever as simple as Dean just enjoying the moment, proudly declaring his love and shouting yes from the roof top as you see in the movies. Oh no, the worst part of that night was Dean never explicitly said yes. In hindsight, he didn't say no either. He simply pressed his lips to Castiel's hoping to convey everything he wanted but couldn't verbally say. While a part of him believed that Cas knew he wanted this as much as Castiel did, Dean just couldn't find his voice. Cas seemed to accept his response or lack thereof, after all he was the one to break from their kiss, his breaths coming in short pants as he smiled at Dean and slid the simple titanium band on.

That was December 24th. It is now mid-January. Dean still hadn't officially said yes to the proposal, nor had he started introducing Cas as his fiance. Maybe it wasn't often needed to make an introduction, but it was still noticeable to others like Dean's little brother Sam and even their friends Benny, Kevin, and Charlie.

That's when he got the idea to make it all up to Cas. Since he seemed to become mute or swallowed his tongue when it came to expressing how he felt, he needed a way to show Castiel that he loved him. He needed to make a grand gesture. He didn't want to do the cliche thing, like ad space in the paper, or even those corny valentines that the local news station scrolled along the bottom of the screen in the morning broadcast. No, he needed something more personal. More them.

Kevin had suggested the video montage, saying that it made sense because it was Dean's line of work that had caused them to meet. Charlie suggested the dinner, because what else says 'shout it from the roof tops' than saying it amongst your family, blood or not? Then there was the final piece of the puzzle, which was Sam's suggestion and no matter how much of a joke it was, it was so perfect for Cas, Dean had to do it.

To start his grand gesture off, he implemented the help of Castiel's family. His parents Chuck and Mari were more than happy to send him what he needed, with the stern promise that he'd return everything in the condition in which he received it.

"Those are priceless memories, honey. They're worth more to Chuck and I than the Holy Bible," Mari reminded him when he called her to let her know the package had arrived. He knew this was saying a lot, considering the three eldest Shurely-Novak children were named after archangels.

He quickly took the box of VHS tapes and DVDs to the basement of their small two bedroom home. They had converted this space to Dean's work area so that he would have the freedom to work from home if needed. Cas had suggested putting a light on the outside of the door so when Dean is working, Cas won't interrupt, potentially ruining any editing work he had been slaving over. At the time Dean didn't understand why the hell he would need it for video editing but now, Dean was grateful that Cas saw things differently.

Dean was in awe of the images that would flash on the screen. Videos of Castiel from the day he was born up until his twenty first birthday would flash up. Dean smiled at the infant bundled in a blue blanket staring wide eyed at the camera as Gabriel's high pitched toddler voice claims the bundle as Thing Two and his. The voice off screen, most likely doing the filming, tells Gabe that his brother's name is not Thing Two. Dean smiles fondly as Castiel's smaller self yawns, his little nose wrinkling and an eye squinting in protest. Dean can't help laugh because he sees that same image every Saturday morning.

More videos show Castiel at various piano recitals, cross country meets in high school, even one giving a speech as he helps promote a female classmate running for student body president. Each new video is copied with Dean's machine, slowly piecing his present together.

Charlie and Kevin are with him when he stumbles across a DVD simply labeled "Cas and the girls." The two are understandably confused but Dean explains that it is most likely of him and his little sister, maybe a few cousins.

He's not wrong. The first half of the DVD has videos of Cas being the brother Dean had heard about on the roof. Charlie gasps besides Dean as a four year old Cas tells the camera that the little bundle in pink is his baby and he'll protect her forever. She wasn't prepared for the squeak of his voice. Dean had two weeks to become accustomed to it and fall in love even more so.

There's another portion of the same video, now Cas and Anna are older, he has to be about six or seven and she, no more than three. Charlie makes a cooing noise and sighs as they watch Cas being the caring older brother, sitting on his knees on the couch as he does his sister's hair into a top knot. Anna turns in the video once he's done and places a loud kiss on her brother's cheek.

The next portion shows Castiel and Jimmy facing each other. They had to be in their early twenties as a blonde haired toddler sits in Jimmy's lap. It doesn't take long for Dean to realize the little girl is Claire as he watches her mimic Castiel's nervous tick of drumming his fingers on his knees. Castiel's voice, the one Charlie and Dean know, calls for Claire to come to him. The little girl crawls out of her dad's lap, pulling herself up. Once up she claps, chanting 'Cas' with each step. When she makes it to him, she falls in his lap, giggling as he makes noises as if he's eating her face while giving her kisses.

"He's good with his family," Charlie states and Dean just nods. That was reason number five that he loved Castiel.

Dean smiled in the mirror when Castiel's reflection came up behind him. He could tell by the look on his face, Cas was frustrated with his tie. The man wore them every Tuesday and Thursday, yet still couldn't seem to get the thin strips of fabric to lay right.

Dean washed the hair product off his hands and made sure to dry them thoroughly before pulling Castel closer to him by his belt loops.

"Why are you wearing a tie?" Dean asks him as he flips up the collar of Castiel's black shirt to make sure the tie is lying flat around his neck.

Castiel tilts his head and studies Dean's face with a small smile. "For two reasons. One, the waistcoat looks better with a tie," he explains before looking at Dean's hands that expertly tied the knot for him.

"And the other reason?"

Castiel hums as if lost in thought. "Because I know you have a kink that involves leading me by said tie and if I play my cards right, you use it to either tie me up, blindfold me or gag me."

Dean's eyebrows raise to his forehead. "You liked that?" he asks, referring to the gagging.

"Very much so, Dean."

Dean shook his head, hiding a small laugh. "It's always the quiet ones."

Castiel tilts his head again. "Did you not like having utter control, Dean?"

"I love it," he answers honestly, pulling Cas close enough that their hips touch. Dean smirks at Castiel's quickened breath, the spearmint of his toothpaste lingers in the air. "I just love hearing you come undone more."

Castiel made a needy noise before crashing his lips to Dean's in a hungry kiss that would have escalated further making them late for dinner had it not been for the insistent knock at the door.

Cas whined when Dean pulled away, making him chuckle. "The night is still young, Cas."

Dean left his pouting fiance to finish getting ready as he went to answer the door. Charlie stood there in a vintage red and black dress that made Dean's jaw drop. The tomboy-ish red head cleaned up nicely and in all the years that they had known each other Dean couldn't ever recall an occasion where she willingly wore a dress. Even while LARPing she wore pants.

"Can it, Winchester," she grumped handing Dean two boxes. "I know I can lead the ships home with these legs." She lifts the hem of her skirt slightly above the knee to show off her lack of a tan. "I think I'm the same color as Casper."

Dean laughed and shook his head. "No, Charlie. You look fantastic!"

She grinned and swung a bit from side to side. "Thanks, you think Joanna will like it?"

"She'll love it. These the final touches?" Dean asked before looking over his shoulder to make sure Castiel wasn't coming.

Charlie nodded. "Yep, the rose boutonniere and completed DVD. Kevin has the digital file at the hall minus your grand finale and Sam has the important box. He said he'll deliver the package when you get there before playback so you don't screw with the timeline."

"Oh, ha ha." Dean rolled his eyes, secretly thanking whatever God above that his baby brother knows how bad he could potentially screw up tonight.

"Is that what you're wearing?" Charlie asked eyeing his ensemble. He looked down at his dark washed jeans and powder blue pressed shirt.

"Well, kind of. I mean I still have to put my shoes on-" he started but Charlie huffed and pushed her way in.

"Yo, Cas! You decent in there?" she called out as she headed to their bedroom. Dean hurriedly placed the boxes and dvd on the coffee table before running after her.

Cas laughed and stepped into the hallway. Charlie let out an appreciative whistle as Dean bit his bottom lip.

"As you can see, I am in fact decent," Cas said slowly spinning in place so that she can see the full outfit. He had gone with his black jeans, charcoal pressed shirt with sleeves rolled up to the elbows, black waistcoat, and the deep red tie.

"Dang, Cas. If you weren't spoken for and I didn't play for the other team, I'd bang you."

Castiel threw his head back in laughter before hugging her tightly. "You look beautiful, m'lady."

Charlie beamed at his compliment. "Thanks, Cas. Now scoot, I need to help your man look presentable."

"I look fine," Dean grumbled and made his way to the bedroom. Luckily for him Charlie didn't torture him for too long. She suggested that he layer his look, allowing him to keep it somewhat casual but also seem dressed up.

Finally, they were on their way to the dinner Charlie had put together. A group of their friends and family were going to enjoy a Valentine's Day party at an Italian restaurant where Dean and Kevin would provide the entertainment. It wasn't anything too extravagant, or at least, that was how Dean was trying to play it off to Castiel. Really it was a surprise for Castiel, a way for Dean to make up for everything he couldn't say.

After some light teasing and nervousness, Dean was able to attach the single red rose to Cas' outfit. There may or may have not been a ton of giggles from both men and soft kisses. Cas even knew Dean well enough, to know that for Dean this was like giving Cas a dozen roses, even if it was a single blooming bud with an accent of black ribbon and a single black feather. For Cas, that single rose and feather meant more than all the flowers on Earth.

When they finally made their way into the restaurant it was clear that Charlie had outdone herself. Candles, bouquets of roses, even red glass stones were placed along the center of the long black tables as centerpieces. A menu card laid on the plates, wine glasses and red chairs placed in their spots for everyone to sit. Off to the side she had set it up like a photo booth, with props and what appeared to be a professional photographer. Dean pretended to speculate, knowing that it was in fact the photographer he had hired to record tonight's events.

The dance floor was small, but big enough that Dean was sure could fit at least four to five couples and to the corner of that, Kevin had set up the audio and visual equipment. Of course Castiel recognized the visual equipment and raised an eyebrow in question to Dean. Dean shrugged it off as needing it for the generic floor art on the dance floor. Thankfully, Cas accepted that and wandered off to where Charlie was, allowing Dean to take a deep breath.

"If you're worried he's gonna say no, I think that's too late, Jerk."

Dean couldn't help but smile at his much bigger baby brother. "I know, Sammy. I'm just worried he's not going to like all this," he explains with a tiny gesture to their surroundings.

Sam shook his head and handed Dean the black leather box, surprised that his brother didn't take the opportunity to call him a bitch, attesting to Dean's nerves. "You know him better than any of us. I'm sure you wouldn't have done all of this if you thought there was a slim chance that he didn't like it."

"What if he hates the movie?"

Sam scoffs into his beer then notices the slightly panicked look on Dean's face. "Are you kidding?"

"Does this look like my kidding face?"

"Dean," Sam puts a hand on his brother's shoulder. "I know this is hard for you to accept but Castiel loves you and I know you love him. You deserve to be happy, Dean. And honestly I think the happiest I have ever seen you is when Cas came into your life."

Dean nodded. "Yeah, it's going to be fine." Sam was pretty sure he was trying to convince himself.

Sam sighed, clearly seeing the fear in his brother's eyes. "Remember, you're doing this because Cas deserves to know, right?" Dean nods again. "This is your way of shouting it from the rooftops. Your words, remember?" Again Dean nods. "This is a really big step for you, but what you're doing tonight, is showing Cas that he's worth it."

Jo and Charlie laughed at the story that Castiel was telling them about work. He loved his job, working with the kids, and seeing the smiles on their faces when they learn something new. His brother Gabe often joked that Castiel brought his work home in the way he handled Dean. Gabe had once thought that Cas' fiancé was too arrogant and self-centered for his baby brother, but Castiel saw the real Dean, not the facade.

Charlie directed Cas to the tables were they sat and Jo picked his brain about the upcoming school play. She was the performing arts teacher at the same school Castiel taught his autistic spectrum class. They had shared ideas on how to incorporate his children as well as turn the Shakespeare play The Taming of The Shrew into something appropriate for junior high students.

"Enough shop talk," a voice Castiel instantly recognized as his twin brother Jimmy chimed in. Castiel was out of his seat and embraced his brother faster than anyone could blink. Jimmy, who was used to his compulsion to launch at people, just laughed and hugged him back.

Before Castiel could ask the question on his tongue, there was a tap on a microphone, getting everyone's attention to Dean in the center of the dance floor.

"Welcome, family and friends. And thank you for agreeing to spend this Valentine's with us," he said. "Before we dig in, I wanted to steal the spotlight and present something special to y'all, but first I need Cas to join me up here."

Everyone laughed and cheered as Dean motioned for Cas to come to him. Castiel was confused at the current change in events but allowed himself to be lured by Dean's call, as he would never refuse him.

"Trust me?" Dean asked Castiel once he reached him, grabbing his hand as if seeking comfort in it.

"Of course, Dean," he responded, his curiosity growing. Dean only responded with a soft, chaste kiss and squeeze of the hand before motioning to for Castiel to sit.

Once Cas was situated, Dean addressed everyone again. "So this is really for Cas, but I wanted you all to be here to witness this. Anyone that knows me, knows that when it comes to expressing my emotions, a cactus is better at it." There were a few chuckles heard, mainly from Dean's brother and Uncle Bobby. "And anyone that knows Cas' and my relationship, knows that he has the patience of a saint—maybe even an angel— when it comes to me." Castiel rolled his eyes at Dean but couldn't wipe the smile off his face, his hand absentmindedly brushing against the feather in his boutineer at the mention of the angel.

"So, Cas, I hope you enjoy and I'm sorry if I went too cheese ball on you." Dean stepped off to the side as the lights in the hall dimmed, the lights of the candles flickering, the shadows of the flames dancing along the surfaces. The wall in front of Castiel lit up, and suddenly Dean was being projected on the wall.

He was sitting in the basement studio, wearing his Dallas Cowboys hoodie and his reading glasses were perched on the top of his head. He fiddled around with something, muttering "sonovabitch" which made the room chuckle.

"Jesus, I hope this is recording," Dean muttered as he leaned back in his chair. He finally looked at the lense, a small smile on his face. "Hiya, Cas," he said to the camera with a small wave. Castiel's own hands clutched at his denim clad thighs to keep from waving back.

"So you're probably wondering what in the hell am I doing now? Well, not now," Dean chuckled in the recording and looked at his watch. "If I'm lucky, you're still burrowed in bed with Frodo enjoying your Saturday ritual of sleeping in until I bring you coffee." Video Dean's smile widened.

Cas smiles and shakes his head but tries to keep his eyes on to video.

"But what I mean is when you're watching this, you're probably wondering what is going on. Well see here's the thing, Cas. There's some things I have to tell you. Things that you need to hear, deserve to hear and for whatever reason, you've been okay with my piss poor attempts to show them instead. So this video, is a grand gesture," Dean chuckles darkly. "If I don't manage to piss you off and you leave, that is." He then groans and stands up. "Good job, Winchester," he mutters to the camera before the screen goes black and when it comes back into focus, the image changes.

Now Dean is sitting there in his green henley and their dwarf tabby, Frodo in his lap. He was scratching under her chin when he started to speak. "Sorry about that last segment. It was suggested that I take it out and start over," he lifted one shoulder to his ear in a half hearted shrug. "I didn't feel it would be authentic if I did that. So here we are. Take two," he smiled and looked at the camera. "Now you know why I do the editing and not the acting." Again chuckles were heard amongst their families and friends.

"So, as I said, you deserve the grand gesture. I didn't think a jumbotron message would work since I know you only watch sports because I do. And I can't write you a sonnet or anything like that since you're the literary major. So I figured I'd stick with what I know. Which left me with a few options that, if I pulled this off, I really can't say one of them." He paused to look down at the cat but Castiel didn't miss the quick flick of his tongue across his bottom lip or the bite on said lip. He knew exactly what Dean was thinking just then and he would have to agree. Dean was very talented behind closed doors.

Dean clears his throat and continues. "You won't let me get you a better car. So that leaves this." He smiles again. "I'll see you at the end."

The video transitions to a very young and tired Mari and Chuck holding two matching bundles. "Tell us about, Castiel," a female voice urges making Chuck smile wider before placing a kiss to the bundle's forehead.

"This little fighter," Chuck starts. "Is Castiel. When we found out that they were twins, we had toyed with giving him and Jimmy similar names."

"No, you were just being mean," Mari chides. "Don't let him fool you, Amara!"

Chuck laughs. "We almost lost him twice. Once in utero about three months ago when he rolled over his brother and got the cord stuck," Chuck explained pushing the blanket from the baby's face as it's fist lifts up. "And we almost lost him this morning."

"It's a miracle," the voice - Amara, Castiel's Aunt - says softly off camera. "That he just found the will to survive."

"Castiel is the name of the angel of Thursdays. Mari thought of it since he regained his breath in the wee hours of Thursday after the doctors were ready to pronounce him as a stillborn."

"He's our little angel," Mari agreed sleepily, smiling at her husband and son.

"Our little fighter," Chuck agrees, smiling down at baby Castiel.

"One of the reasons I fell in love with you, Cas," Dean's voice is heard over the video, now showing little Castiel looking at the direction of the camera as if he knew what was there regardless of what science says. "Is you never back down for a fight or give up. It's something you've apparently done since birth."

Castiel gasps and tries to find Dean in the faded light. Did he just say he loves him? Castiel wondered as his heart raced. He had longed to hear those words and even hearing them now, he thought he was dreaming. There was no way Dean would say that out loud with everyone here.

The video continues with various clips of a young Castiel playing with his siblings. While there were a few of them you could tell the older ones were tolerating their baby brother because they had to. There were also clips of the young boy caring for his twin when he had scabbed his knee after falling, of course of him doing Anna's hair, and having tea parties with Claire.

"I love the way you're patient, kind, compassionate and caring, even at a young age." Dean's voice is heard as various clips of an older Castiel flicker on. Videos of him volunteering with Habitat for Humanity in high school, protesting outside of a women's clinic against those that wanted it shut down. Giving an impassioned speech in his high school quad.

Recent images start to surface, ones that Castiel remembers but doesn't remember being photographed. He could clearly hear Dean laugh as Castiel throws a pillow out at him, trying to sound put out by Dean's antics, but the small smile on his lips hints that he's not mad at all. Another clip of the same smile when Castiel came home to find little Frodo meowing up at him from the back of the couch. Again the same smile as an obviously drunk Castiel hides his face in Dean's chest, as Dean laughs at the camera.

"I love your little smiles. The ones that seem so shy and unsure, but tell me you're happy in that moment. I love them as much as I love your full smile," Dean narrates as the clips shows various situations of Castiel laughing and smiling with friends and family. "You know the one. The one you hate. You say it's all gums, but what I see is the man I love genuinely happy with that wide smile. The way your nose crinkles and your eyes dance."

There it is again, Cas thinks. Letting the fact that Dean loves hims wrap him up like a warm soft blanket.

Suddenly the clips start to fade out, now alternating with pictures of them as well as single shots of Cas. Castiel bites his lip to keep from laughing at the song choice, knowing that Dean isn't the Staind fan between them. Castiel gasps at the last picture. It's from the night of their first kiss. Dean holding the lapel of Castiel's trench coat as Cas reaches for Dean's leather jacket. Castiel remembers that night so well that even though it was a little over three years ago, at times it still feels like yesterday.

"This song was playing in the bar when I finally got my head out of my ass," Dean chuckles, suddenly appearing from the shadows besides Castiel. "You'd tease me for months saying that this was our song."

"How did you get that?" He points at the picture, the memory forever caught in time.

"Sammy," Dean answers his emerald eyes never leaving Castiel's face.

"You're welcome!" Sam calls out, making everyone laugh. Dean fights the urge to flip him off, instead focusing on Cas.

"The song is our song though, Cas. Because all I want, all I ever wanted was you." He gets down on his knee and Castiel looks at him in confusion.

"Dean, I think we've done this already."

"You're right, you have. But I was an asshole and never verbally said yes." Dean explains with a shrug and sad smile.

"You never needed to, I knew," Castiel says simply.

Dean opens his palm to reveal the black leather box. "No, you deserve to know that I chose you. I chose us. I'm sorry, Cas. I'm sorry for never telling you that I need you. For never telling you how much you mean to me." He opens the box to show the ring inside, similar to the one Castiel had given him, titanium with beveled edges, but this one has one single diamond.

"Most of all, I'm sorry for just now telling you that I love you, Castiel. I'm not good at this but would you want to grow old with me? Maybe have some kids some day?"

"Oh, Dean," Cas breathes before launching himself at Dean, knocking the kneeling man onto his rear as his hands cradle his face. "Of course," he says against Dean's lips.

Dean smiles and wraps his arms around Cas, kissing him as a weight lifts off his shoulders now that Castiel knows how he truly feels, even if it took a chick flick moment to do it. Castiel sighs against Dean's mouth allowing for Dean to probe further and taste his fiance.

"Hey, love birds! Dial it down a notch or I'm getting the hose!" someone shouted, making Cas pull back and Dean growl.

"Happy Valentine's Day, Dean."

Their engagement didn't last long, they were married September eighteenth of that year in a small outdoor ceremony under the stars with their friends and family in attendance. They had chosen this date as it was the day they met and their lives were irrevocably changed.

While Dean still struggled with verbalizing his emotions, he never forgot to tell Castiel how much he loves him and needs him.

Even today, the day of their wedding, as the champagne bottles popped open for glass to be refilled to their brims, Dean does not hesitate to remind Castiel how much he loves him between every single kiss.


Special thanks to Linsadair for reading this over for me. Hope y'all have a happy Valentine's Day! :)