Dean had never been the biggest fan of Valentine's Day. It was a holiday for those "in love", where they spent insane amounts of money on each other and acted all cutsey. For people who weren't… it got pretty old pretty fast. Dean and Sam passed the day as kids with a movie on tv and some candy that they had splurged on. As they grew up, the older started getting girlfriends (even a boyfriend or two without telling his father) in february, just too hook up with them on Valentine's Day. The Winchesters would usually be gone with the wind soon after, sometimes only days later. That was one of the few perks of their dad's inability to get his shit together- no long term commitments, even if it got a little lonely sometimes.
After Sam went off to college, Dean finally settled down in Sioux Falls, near his surrogate father Bobby. For the first few V-Days, he had been too busy working in the mechanic's shop to even think about it. He didn't really mind; a lot of the guys had wives and kids to dote on. When Dean gained some seniority, he hung out with friends in various bars. Eventually, as it goes, everyone started pairing off and doing their own thing. Benny and Louise, Dean's only real girlfriend Lisa and some random dude, even Sammy started ditching the Valentine's Day call to hang out with his fiance, Jess. The only consistent person was Charlie, his best friend. They played wingperson to each other and tried to get the other laid. However, even she fell prey to a chick named Gilda when they entered their thirties. That left Dean alone for two whole years, two whole weeks devoted to drinking and drunken hookups. He was starting to think that he'd be alone forever.
This Valentine's Day, though, three years after Charlie ditched him, was different because of one person: Castiel Novak, a preschool teacher and Dean's boyfriend of nearly eleven months. They had a pretty cute story; at least, Dean thought so. Castiel and Jo worked together, and she sent him straight to Singer's autoshop to Ask for Winchester when he started having car troubles. The blonde was always trying to play matchmaker, having set up the mechanic and Lisa so long ago. Anyway, Dean took one at those ice blue eyes walking towards him and fell- hard. There were a couple of months of figuring out how to keep talking to Cas, but he finally manned up and asked him out. They had been happy since then.
So for once, the eldest Winchester had plans with his boyfriend like other people do. Not many people knew it, but Dean was a pretty big romantic,. though not a total sap. Unattached sex was great, but he loved holding hands and cuddling and actual dates. Because of this, he had the night planned. He would get home from work at about six and shower, since he'd be covered in grease. Then, he had already reserved a table at minerva's restaurant. Thank some higher power that Dean used to babysit the owner's kid, Krissy, and the guy let him in pretty much all the time. Everything would be going awesome until dessert, when a chocolate shake would come out with a ring on one of the straws.
Proposing was something that Dean had been thinking about for months. Hell, he'd wanted to do it since the first day that he had met Castiel. A month or two back, Charlie had went with Dean to Crowley's jewelry store to deal with the old grump for him. Crowley was pretty hated around Sioux Falls, but he had the best collection around. Charlie was good at dealing with people, so she was a huge godsend, distracting him so that Dean could focus. He had spent his entire Christmas bonus on the perfect ring, but it was worth it.
Okay… Maybe he was a total sap. Just maybe. He had never really imagined himself like this until he met his angel. Dean had always pictured himself being that awesome uncle to everyone else's kids, the single bachelor who treated all of them to whatever they wanted. He had been cool with that. Dean had even planned out a lot of his single future. He wanted to stay in Sioux Falls for a couple more years and try to get his associate's degree in mechanics. The older Winchester had always regretted not going to college, but he was trying to make up for it. Then, he was going to travel out to California to be with Sam, jess, and whatever kids they had popped out by then. That covered at least six or seven years, but after that? Dean wasn't entirely sure. He was considering going overseas for a while. But then he met cas, and all of that changed. He didn't know where he wanted to be anymore, but it didn't matter as long as he had Cas.
He got home later than he expected on that Valentine's Day, but as he knew that their table would be held indefinitely, he didn't really worry about it. Dean kissed Cas passionately and handed him a large bouquet. Cas's face flushed as red as the wrapped roses, and Dean excused himself to run up and take a shower to get all of the grease and sweat from his job off before he got caught up in his boyfriend. Once he was out, he threw on the singular suit that he had for special occasions (with all of his friends getting hitched, it was getting a lot of use) and a tie, straightening it as he walked. he was really excited to… Stay home.
Cas was all dressed up; god, he looked gorgeous. His raven black hair was all styled and man, he just killed the suit he was wearing. It put his partner to shame. It made Dean how on earth he had gotten so lucky. But there was one problem- Cas was fast was curled up on the couch, face smushed into the back cushion. It was pretty freaking adorable. Dean glanced at his watch and saw that it was only 7:15. Something must have really worn Cas out at school. he wasn't going to wake his boyfriend up, so he kneeled down and gently picked him up bridal style.
Dean headed up the stairs to their bedroom, feeling a nose nuzzling into his neck and grinning. He loved it when Cas was all touchy-feely. It was so endearing. Plus… Dean really liked waking up next to someone. He liked the arm thrown across his chest, the cheek rubbing his chest, their legs tangled up under the covers. Lisa had never been a cuddler when they were together- she tended to run hot under her skin and wanted sex all the time. But Cas was content to just snuggle.
He gently sat Castiel up on the bed, stipping him down to his underwear. Blue eyes blinked sleepily open while he was doing this, not fully awake. Suddenly, his face changed to a look of "oh shit".
"Dean, I'm sorry! I didn't mean to fall asleep. I just had a really long day. We were supposed to go out and-"
Dean cut him off. "It's okay, Cas. We can go out another day."
The other man nodded tiredly, mumbling another sorry.
"Get into bed. I'll be there in a minute," the green-eyed man smiled, starting to loosen his own tie. he got undressed before climbing into bed, where Cas was snuggled into the covers. Dean laid down, a warm body with an intoxicating scent wrapping around him. Just as he started to doze off, comfortable, he heard a sleepy voice from next to him.
"Yes," Cas mumbled into his neck.
"Yes? Yes to what?"
"I found the ring box in your sock drawer two weeks ago."