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Dean Winchester’s not sure when, exactly, he fell for his best friend and roommate Lucifer Milton. He’s not sure if he could ever pinpoint it.
It could’ve been the first week of freshman year when Dean walked in on Lucifer wearing an AC/DC t-shirt and pinning up a Led Zeppelin poster. He apologized for the state of the room, but he just got the time to decorate. Dean helped him out.
It could’ve been when they were stuck in world history and Lucifer spent half the class correcting the professor because, as he put it, “History was a lot more gay and bloody than you would think.” The professor didn’t like Lucifer much, but there was nothing she could do about it.
It could have been the time when Lucifer sheepishly asked Dean if Dean could teach him how to do basic maintenance on cars so he wasn’t doling out money for a mechanic for the simple things.
It might’ve been sophomore year, when Dean hooked up with Lisa Braeden and she tried to accuse Dean of getting her pregnant and Lucifer stuck by him. It was Lucifer who insisted Dean requested a paternity test which ended up saving Dean’s ass. Lisa was furious and tried to get back at Lucifer by announcing that Lucifer was gay. At their somewhat conservative college, this would’ve created a big impact had it been anyone else but Lucifer. In retaliation, Lucifer created and sewed a giant pride flag onto the back of his denim jacket and was even more flamboyant with his personality. Lucifer got some shit for it, but Dean was there to protect his friend.
It could’ve been the second half of sophomore year, when Lucifer helped Dean with his advanced math classes because Dean was getting lost. It’s not that Dean wasn’t good at math- he was actually incredibly good at it. It was the whole ‘show your work’ philosophy that was getting Dean in trouble. Lucifer was patient and helped him through it, when he wasn’t busy furiously typing up things for his English class.
It might’ve been the first day of junior year, when Dean arrived at the dorms ready to begin his third year of college and was greeted to Lucifer handing him a pie he made from scratch. Dean was actually ready to fucking propose to Lucifer at that, as the pie was one of the best he ever ate.
Or maybe it was right before Christmas break, when Dean was worried that he wouldn’t be able to make it home for the holidays because money was tight. Dean knew Lucifer was rich- anyone who hadn’t been living under a rock would’ve known who Lucifer and his family were- but Lucifer never really flaunted it. Lucifer almost didn’t care about it. Dean could’ve cried when Lucifer handed him an envelope containing a couple thousand in cash, more than enough to drive home and see his family as well as buy them gifts. Dean used that money and his father’s connections to buy Lucifer his favorite bottle of whiskey as a late Christmas gift.
Whenever it happened, however it happened, Dean fell for his best friend and now in their senior years of college, on the verge of graduation, Dean felt lost as to what he should do.
Turned out, Lucifer knew what to do.
It was Lucifer who got the balls to ask Dean out on a date. It was Lucifer who initiated their first kiss in the front seat of Lucifer’s baby blue ‘64 Ford Mustang, tasting of mint flavored gum and bitter coffee and something that was uniquely Lucifer.
And that’s when Dean knew he was in deep for his best friend.
They rearranged their room, knowing they’d have to rearrange it back when they graduated. They shoved the two beds together to create one large bed and moved Dean’s desk next to Lucifer. They placed down one of the thickest throw rugs Dean’s ever seen onto the floor so Dean could work on engines in the safety of their dorm room and not be in the garages all night.
They were there for each other when their individual nightmares got to be too much- Dean’s former relationship with Alistair Picasso had fucked him over one too many times, and Lucifer still harbored nightmares from his first pride parade when some thugs beat the shit out of him and would have raped him had Michael not been there with some sort of unholy righteous older brother anger. They took comfort in each other, wrapped up in the knitted pride blanket that one of Lucifer’s younger brothers, Castiel, had made for him and murmuring soothing words.
Both were hesitant, yet determined when it came to sex. Dean’s past relationships had been hurried when it came to sex, the goal being fucking and getting fucked. With Lucifer, though, Dean found himself wanting to take his time. And Lucifer was more than okay with that.
It was no one’s surprise that Lucifer and Dean started dating, and both the Miltons and Winchesters met up at the college to surprise Dean and Lucifer, so they could meet the other’s families and get to know them. Dean had to resist the smirk when he saw his younger brother get starry-eyed at Michael Milton, who was on his way to becoming an attorney with the bar exam. Michael seemed rather taken with the younger man hanging onto his every word and helping him to study for it over Christmas break. Lucifer even admitted he’s never seen his older brother taken with another person like this before. John and Mary Winchester got along well with Chuck and Naomi Milton, and Adam seemed to enjoy spending time with Samandriel, Lucifer’s younger brother that was also Castiel’s twin. The three eleven year olds seemed to have a fun time together, but for some reason Adam and Samandriel seemed drawn to each other. Gabriel enjoyed hanging out with Dean and Lucifer, although Lucifer went to grab himself a drink when Gabriel and Dean began arguing about the TV show Dr. Sexy, MD , because of course they’d bond over that, as well as their mutual love for pranking their brothers. Dean’s fairly certain there were tears rolling down his face as Gabriel described removing all of Castiel’s clothes and pillows from his room and replacing them with watermelon flavored jelly beans; Gabriel nearly went mute with laughter when Dean recollected the time he filled Sam’s shampoo bottle with Nair.
All in all, being together for Christmas was one of the best gifts Dean had ever received. Lucifer got him a denim jacket with the bisexual pride flag sewn onto the back, so that they could have matching pride jackets, while Dean gave Lucifer some ancient book (okay, 16th century isn’t ancient, per se, but give Dean a little credit) that he had read their sophomore year in English and proceeded to never shut up about.
The rest of their senior year was passed with lots of study sessions in the dorms, watching movies with a bottle of whiskey and a bowl of popcorn in between them, and general panicking over what to do next. Lucifer decided that he wanted to get his Master’s degree and prepared for the GRE while Dean was frantically working on getting parts for a ‘junker’ his uncle Bobby had that he wanted to fix up online.
They got into fights, they didn’t always talk about how they were feeling. Both Lucifer and Dean had learned the ways of ‘conceal, don’t feel’ and it ended up with communication issues for the both of them. This was normal, as they had been roommates for four years, but now it pained Dean any time Lucifer decided he was going to sleep in the common area instead of their makeshift bed; and it didn’t soothe Lucifer’s aching pride when Dean had left without making enough breakfast for the two of them.
But they worked it out. They always did.
Lucifer was beyond thrilled when he was accepted to a top tier graduate school for English, and Dean had already decided he was going to move with him. Now that Sam was going to Stanford, moving to Berkeley didn’t seem that far off.
They moved, got a one bedroom studio apartment with no heat or air conditioning, but it was perfect because it was their’s. They divided up the bills and Dean found work in an auto shop, working on fancy cars driven by fancy, rich people while Lucifer became a children’s librarian. Once a month, they’d drive down to Stanford to check on Sam, although Sam was mostly good as he was attending Stanford on a full scholarship and was working in the college bookstore. He was dating a medical student named Tyson Brady, although Dean could tell by the set of Lucifer’s jaw that his own boyfriend did not approve. Dean didn’t like Sam’s boyfriend either, but simply informed Sam to be careful.
Their lives were busy between work, school, and paying the bills. They managed to live reasonably okay for living in California, where Dean’s fairly certain that the only reason prices were so high was because most everything in California was organic. Not having air conditioning was the worst, because the summers were sweltering, even more than in Kansas and the ancient AC unit Lucifer had installed barely cooled down their bedroom.
Sam broke up with Tyson Brady his sophomore year, not wanting to be associated with the drugs and whoring that his now ex was doing. Dean and Lucifer did their best to comfort Sam, who simply ducked his head down and worked on school.
They got visits from their parents. John and Mary came around on Easter; Chuck and Naomi around Christmas. Michael visited often, as he lived in the San Francisco Bay Area after passing the bar exam. Michael and Lucifer either loved each other or hated each other, it was a toss up as to what had happened. Normally, though, the brothers loved each other and Dean enjoyed having Michael around. He was a stuck up prick a lot of the time, but he enjoyed good food and that was good in Dean’s book.
No one was surprised when Lucifer proposed to Dean. They had all seen it coming.
Nor were they surprised when the two of them eloped in Las Vegas
All in all, Dean Winchester and Lucifer Milton were very, very happy together.
And it all started out as being roommates.
So while Dean didn’t remember when he fell in love with Lucifer, it didn’t matter.
Not when Lucifer felt the same way.