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The thing is- Dean’s protectiveness of Sam doesn’t ebb as they grow older. It changes as they age, but whether they are six and two or sixty and fifty-six, Sam will always be his baby brother.
So when his relationship with Rowena is revealed, Dean’s protectiveness rears its head pretty fiercely- perhaps an overcompensation for Dean not seeing it in the first place. He’d noticed, of course, that something about Sam was…lighter. Happier, maybe, than he’d been in a while. Dean had chalked it up to a slowdown in cases and a break from their norm of warfare with heaven and hell- not boning the redheaded witch.
It's not that Dean doesn’t think Sam can’t make his own decisions- it’s just that in the romance department…Sam’s track record is far from stellar. And while Rowena was their ally these days, Dean wouldn’t exactly call her their friend and giving her any more of their hard-to-earn trust was harder than Dean would like to admit.
Rowena’s presence becomes more and more frequent around the bunker as the days turn to weeks turn to months. Dean becomes used to spotting her crimson curls disappearing back into Sam’s room in the early mornings, two steaming mugs in her hands before the door snaps shut behind her- grows annoyingly fond of the way her hair clogs the shower drains in the locker room, how he finds it on the couches in the library, on the counters in the kitchen.
Somehow, it isn’t until he’s texting Cas one night, half paying attention to where he’s walking, that he realizes how deep his brother has fallen. He’s lingering in the doorway of the library, leaning against the door jamb as he argues with the angel about crunchy and creamy peanut butter for the millionth time, when he looks up at the quiet murmuring he hears.
Sam and Rowena are curled up on one of the couches, the witch pressed against Sam’s side with her head on his shoulder- his brother’s got his arm around her shoulders, and then their fingers are twined together, palms pressed close. Their faces are close as they converse quietly, and Sam’s free hand touches her chin tenderly, thumb smoothing down the line of her jaw before touching her pulse gently.
When Sam draws her mouth to his, Dean feels like he’s intruding at how intimate it is; he turns back down the hall to the kitchen, feeling his phone vibrate with Cas’s response, and thinks maybe it was time he laid off on Sam for his choice in romantic partner.
_
Castiel had always found human relationships interesting. As an angel, he’d watched from afar as relationships and bonds were formed, as humans fought for love, sometimes to the death.
Here on earth, experiencing relationships of his own, Castiel still found them confusing. Dean tended to brag about his nights out, his ‘conquests’- though, as time passed, those nights grew less and less frequent. Sam, on the other hand…Sam was quiet about his private life, or what semblance of a private life he had, as entangled as they all were.
It surprises Castiel that Sam does not hide Rowena the way he had all his other romances.
She waltzes her way into the bunker when she comes to stay the night- kisses Sam without apology in front of them, holds his hand when they all sprawl in the library for movie nights. When Sam makes dinner, Rowena perches herself on the stool and teases him while he cooks- begs kisses off of him until he indulges her, smiling against her mouth as her nails tug lightly at the collar of his flannel shirt. Her favorite spot in the mornings before she’s fully awake is in Sam’s lap, tucked under his chin as he clicked away on his laptop, his chin resting on the top of her head.
Castiel finds it all…curious- finds them, in particular, curious. Finds the way they bicker and fight as they research and perform magic for cases infinitely interesting, given that every night they disappeared into their shared bedroom and locked the door and did not reappear until morning. Sam smiles when Rowena snarks at him, flushes happily when she teases him endlessly and tugs the ends of her crimson curls with a grin to rile her up until she’s grinning just as widely as he is.
Happiness shines from them both like radiant rays of light, warm and bright, and Castiel stands in their glow, out of the shadows for the first time in a long time.
_
Rowena and Sam fascinate Jack.
At first, he thought they hated each other- they were constantly fighting, arguing over research and sniping about spells and getting in each other’s personal space despite the fact that Rowena was an entire foot shorter than Sam. It wasn’t until Jack was up late one night, fixing himself a midnight snack, that he’d heard them- they’d been out together, apparently, returning with their hands skimming each other’s bodies and tumbling down the hall before shutting the door to Sam’s bedroom door firmly behind them.
Eventually, Jack learns that the barbs they throw at each other are a part of their love language- the same way that Dean’s soft, affectionate teasing of Castiel was part of theirs. There’s a tenderness to the darts they throw that softens the blows before they even land, and Jack likes watching the tennis matches between them, the volleys of their arguments across the tables in the library as Rowena suggests one spell while Sam counters with another.
He likes watching the little dimple appear in the corner of Sam’s mouth that means Rowena has won, or the wink the witch throws Sam when she concedes that he’s offered a suggestion that’s actually better than hers. Rowena is smaller than Sam physically, but her personality is so large she refuses to go unheard, making her presence loud and large.
(Jack likes it less at night, having the room beside them and supernatural hearing, however- invests in the best earplugs money can buy, and expensive headphones and a heavy metal playlist Dean makes for him. Sam only flushes a little when he sees Jack leaving his room in them, hears the loud music and understands he and Rowena hadn’t been as quiet as they thought. Jack just rolls his eyes at the taller man’s sheepish shrug and skips to the next song on the playlist as he heads to the kitchen, following the scent of Dean cooking bacon.)
_
Waking up from Heaven to find her sons- her babies- as grown men, grown hunters, at that- isn’t a cakewalk for Mary. But as time passes, she relearns her own children, relearns herself, and tries to find her place in a modern world.
The thing she finds strangest, though, is seeing her sons in love.
It’s not that she doesn’t enjoy it- she likes the soft flush of Sam’s cheeks, the little grin Dean gets. It’s just that when she’d pictured the two of them, in the very far future, bringing their future partners home, they’d been nice, normal girls from college. Not…not, well, an immortal centuries-old witch and a literal angel from heaven itself.
The first few times Rowena appears at the bunker, Mary doesn’t quite know what to make of her. She’s sharp and smart and funny, dressed impeccably and never a hair out of place- but Mary can’t help but wonder, warily, if Sam’s under some kind of spell, falling for this impressively powerful witch.
But the longer time goes on, the more Mary relaxes. Sam is so happy. His whole face lights up every time Rowena shows up, especially unexpectedly- the click of her heels on the steps has him hopping out of his seat to greet her, face spread wide in a grin, and then he’s tugging her into him, her small frame engulfed in his own in a tight embrace.
She observes her son whenever the witch is around- the way he’s happiest when Rowena is invading his space when he cooks, when he’s researching in the library, when he’s training on the mats. He’s wrapped around her slim, powerful fingers, and Mary is fairly certain there was no place else he’d rather be.
Much like Dean, and the angel, she muses, watching her eldest clink his beer against Castiel’s in the kitchen, the two of them closer than they needed to be as they shared a drink in the dim lighting of the bunker’s kitchen. She kept walking to her room, bemused smile curling her lips.
_
He is still unsure why, exactly, he is back- had just felt in inexplicable tug, and then, suddenly- he was back.
Hell was easy to reconquer, his minions quaking as he reestablished his mantel as King of Hell with barely a drop of blood on his designer suit. The throne barely feels any different as he sits upon it, though Crowley himself feels a far different demon than when he last gazed upon the fires of Hell.
He avoids Earth for a long time. Arriving back from the Empty to learn his mother was romantically involved with a Winchester, of all people…it left a sour taste in his mouth. She’d spent so long telling him he was weak for dealing with them, that his reign as king would be forgotten for his involvement with them, all to wind up in bed with one herself.
Rowena writes to him rather frequently, but he lets the letters collect in stacks, unread, for weeks. He has a rotation of demons tailing her, but they send reports that she spends most of her time in the Winchester’s bunker, holed up with her new boytoy, Sam Winchester, and the rest of the gang. It infuriates him, not knowing what she’s doing.
Eventually, the letters prove too taunting, and he opens the first one, reading the scrawling handwriting with curious eyes. It’s an apology- or at least, as much of an apology as his mother will ever be capable of. She asks to see him, or at least meet with her for lunch, and Crowley almost feels bad for ignoring the letter for so long.
The following letters are much the same, and when Crowley reaches the bottom of the stack, it’s a request for lunch that day, in an hour’s time. He wars with himself for a bit before eventually he finds himself in front of the bistro, staring through the window at a familiar mess of red curls, waiting for him.
“Hello, Mother,” he greets, sliding into the seat across from Rowena with finesse. The witch looks up at him, blinking in surprise from where she was setting her napkin across her lap.
“Fergus- I was beginning to think you’d never show up,” the smile she offers isn’t accusatory, merely pleased to see him, and Crowley frowns.
“You aren’t angry it’s taken so long?” he asks, and Rowena shakes her head- reaches across the table to curl slim fingers around his wrist and squeeze. He blinks stupidly at the small diamond that sits on the fourth finger of her left hand, and she flushes as she withdrew her hand. “You’re marrying him?”
“I love him,” she answers simply, folding her hands before her, and Crowley’s lips part to speak, but she beats him to it. “I know it seems insane to you. But you were gone for a long time. I’m different- as much as you may not want to believe it, Fergus. And Samuel…he makes me better. Makes me want to be better.”
Crowley’s brows furrow, and he studies her for a long moment as they’re brought food Rowena had obviously preordered- two Caesar salads, extra dressing on his.
“You remembered,” he said, and Rowena nodded, smile softening just so in the corners.
“I’m trying,” she says, and Crowley can’t help but feel something twinge just south of his breastbone. “I know I’ll never be perfect, but…I want things to be different than they were before.”
Crowley’s mouth twitched, and he speared a piece of chicken with his fork, allowing a half-smirk to curl his lips.
“Can I torture Sam? Just a little?” he asks, and Rowena rolled her eyes. “Call him Dad?”
“Just eat your food, Fergus.”