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"Will You Marry Me?"

Summary:

His eyes wandered down to Sammy’s hand, and that was the chick flick of all chick flicks: imagining the curve of a small silver band gracing his little brother’s paw, the ultimate symbol of Sammy belonging to Dean, and Dean belonging to Sammy.

He was Dean Winchester, of course he jerked off, ring on his finger, Sammy on his mind.

Or: that one fic where Dean accidentally proposes to Sam.

Notes:

This piece is the first part of a little series following the fluffy retired lives of our beloved brotherhusbands, written for the fluffy july 2026 challenge.

prompt: day 7: happy tears / will you marry me

(See the end of the work for more notes.)

Chapter 1: Dean Winchester is not doing chick flicks

Chapter Text

There was one truth Dean had always been sticking to: Dean Winchester was not doing chick flicks. He was living for the moment. Moments filled with Sammy: his little brother placing little bites alongside his jaw. Or moments with Dean buried inside his brother, drawing the most wonderful gasps and whines from him.

These were good moments, not chick flicks moments. Blowing off steam, indulging in their own post-hunt madness, letting mutual understanding and need wash over them until they were lying curled up against each other, blissful satisfaction numbing their pain and forcing silence upon their spinning minds. That was the Winchester style, filed into something perfect throughout the many years of being brothers. Completely normal, regarding their completely abnormal lives, or?

In retrospect, the perfect facade started to crumble in Vegas. That one day when Dean expected another case (he was, in fact, not wrong about that), but the church door opened to his widely smiling brother, dressed up and astonishingly beautiful – for a weird second Dean thought that this was it: dreams he had never allowed himself to have coming true. A wonderful dreamily second of Sammy taking his hand and pulling him down the aisle up to the altar, where only a small little word, more a syllable, was expected from Dean. “Yes. YES!” his mind screamed.

He was just about to throw all his non-chick-flicks overboard to say it out loud “yes, yes, yes, of course I wanna be with you forever, as in together-together.” But then it hit him like a punch to the stomach: It was all about Becky and Sam and Sammy’s gorgeous smile was for her, not him. Then the case unfolded in front of him and it was the usual flow of getting Sammy back, saving Sammy, hunting things. No time to scold his own brain for its own weirdness.

However, the thought was planted. An evergrowing ugly pest squidging his insides, the Winchester style slowly dissolving to leave space for chick flicks, or rather: Hallmark movie flicks.

The case was solved, Sammy saved from crazy Becky. But the feeling in his guts stayed to overwhelm him whenever they passed a church. Sammy’s profile against the passenger side’s window was an ethereal sight, his dimpled smile easy to imagine with stained glass painted with religious symbols behind him. Lately it was getting way too difficult to concentrate on the road. Sammy had always been pretty, halo crowning his stupid hair, the kind of halo only Dean could see – but now it was not about primal needs and the chance to get off as much as he wanted. 

Now it was all about them, together. The unspoken promise Dean suddenly needed to hear, spoken in front of the altar – exclamation in front of God and every supernatural being out there. Together-together with Sammy. 

And then it was them, in that church, Sam in front of him, weakened, dying, and all Dean could think was ‘no, not like this’, because this was not what he meant when he daydreamed about stained glass and churches and promises and exclamations. “I made you a promise... in that church. You and me. Come whatever.”

But it was not enough, his hungry mind still not sated. 

“Your family, you do anything for them, don’t you?” Lily Markham asked when they were puzzling together the pieces to save the world from a group of Nachzehrers. 

“Absolutely, but not if it costs too much.” Dean replied, usual chuckle rolling from his tongue easily, but watching Sammy through baby’s window, smiling and flirting with the lady at the cash desk was almost too much. 

Family.

He pushed away the thoughts Winchester style, tried to unstare whenever he caught himself being stupidly glancing at Sammy, asking himself if they were already together-together, or if it was just meant to “clean the pipes”, as he had phrased it himself too many years ago when he convinced Sammy to “live a little and see how your big brother does it.”

Being alone in the bunker, retired hunter and everything, did not make it any better. 

You and me, come whatever. But was it really like that? Come whatever? 

His eyes wandered down to Sammy’s hand, and that was the chick flick of all chick flicks, imagining the curve of a small silver band gracing his little brother’s paw, the ultimate symbol of Sammy belonging to Dean, and Dean belonging to Sammy. That was what family meant, right? 

But then he remembered that no, marrying your brother was not the definition of family, not in Kansas and most possibly not elsewhere. 

Dean got all antsy, giving baby another full clean-up until her varnish glanced and Sammy gave him suspicious looks (to be honest, Sammy had all the rights to wonder, because the whole stare-clean-ritual happened in frequent cycles).

What was even the problem? Not that Sammy was not wanting him, his feral excitement when they did it in the bunker’s kitchen or on baby’s backseat or in the Dean cave or in the alley behind Lebanon’s diner (or wherever else, Dean had lost count years ago and he was not fastidious either) was sometimes quite overwhelming, even for Dean’s stamina (a fact Dean would never openly mention, of course). 

But Sammy did not want him like that, surely not. It was just a pleasant agreement. Blow off steam with your brother until you find someone and leave, this time forever.