A/N: I wasn't expecting to continue this particular story, but then bagelcat1 had to go and post a plot-bunny-ridden review on 'Table for Two' and here we are. Consider this a prequel to that fic, but both stories can stand alone (at least within my Saileen AU) just fine. Warnings for mild language, references to sex, and feels. Reviews are love and occasionally inspire more stories!

The blue felt on the ancient box is worn through on the corners, revealing the cheap cardboard underneath. The diamond is so filthy as to be opaque, and the setting is austere, so unlike the popular asymmetric flourishes adorning the rings safely stashed in the glass case beneath his fingers. Sam wishes he could do better for the woman he loves so dearly, but his full scholarship doesn't cover things like food and rent, nevermind extravagances like ornate diamond rings. His minimum-wage job at the bookstore barely covers the first two.

The jeweler examines the ring with an appraising eye. Sam shifts nervously, wanting to apologize for its appearance and apparent low quality. It's my grandmother's, he wants to say. My mother's mother. I know nothing about her beyond her name. That box has been carted across the country more times than I can count and has somehow survived being pawned off at least three times for ammo. I bought it back myself the last time with money I hustled from a poker player in Detroit. Dad doesn't know that I have it, and neither does Dean. It's the most valuable thing I own besides my laptop, and one of the last things I have from my estranged family.

But Sam doesn't say a word as the jeweler takes the ring to the back of the shop. It's a small place, tucked in the corner of a small strip mall not far from campus. The dust piling in the corners is probably older than Sam. The jeweler himself has the ageless quality of someone so deeply stuck in a rut that they haven't seen the sun in decades.

"It's a good stone," the greasy-haired man hands him back the ring. It sparkles in the dim light of the shop. "Do you need the band resized?"

"No, thanks," Sam twists the ring back and forth, playing with the light refraction and imagining it on Jessica's hand. Thankfully her slim fingers are a perfect match for his long-gone grandmother's. A resizing would mean another month of ramen and beans for dinner. Luckily the jeweler offered to clean it for free.

"Here." A small box is shoved in his direction. The velvet is a glossy new maroon, the silk inside shiny instead of threadbare. "On the house. Good luck son."

Sam bites back a reflexive "I'm not your son" and smiles instead. The ring isn't much, but at least it's clean and presentable now. Hopefully Jessica won't mind. He promises himself that once he graduates and gets a job as a lawyer, he'll buy her the biggest rock in the fanciest shop in California. She deserves it, after all.

The maroon velvet is charred black around the corners. It smells like smoke and burned dreams, and Sam can hardly bear to look at it. The ring inside is untouched, almost as clean as the day he put it inside. It was one of the few things he salvaged from their ruined apartment. The box had lived in the bottom of his duffel for a while, and then in a hidden corner in a storage facility filled with various hunting paraphernalia in Maine. When they moved the more valuable of equipment from there to the more secure Bunker, Sam had slipped the box into his pocket and then his cigar box of memories in his room. Dean doesn't know he has it. Sam almost wishes he didn't have it either.

"Sam?" He almost drops the soot-smudged box at the sound of his mother's voice. "What's that?" she asks with innocent curiosity.

He wants to hide it, to tell her that it's nothing. He wants to ask her why she came to his room and what's Dean up to and if she knows where Cas is and does Jack still want to go to high school in town this fall? But he doesn't. Just hands her the box and tries not to wince when the burned hinges creak open.

"Oh my," she gasps. "Is this my mother's?" He nods as she takes out the ring and admires how the diamond catches the light. It doesn't fit on her finger: it's far too small.

"What happened to the box?" she asks innocently. Sam swallows down the lump in his throat. It was a long time ago, he rationalizes. A lot of time and a lot of Hell has passed under the burning bridge since then. This is nothing.

"The fire," he can get out the words if he says them slow and softly. "The fire that killed Jessica."

"Like me," his mother understands instantly. "Oh honey, I'm so sorry." There are tears in her eyes as she pulls him into an awkward side-hug. Sam's eyes are too dry, and he blinks repeatedly to try to relieve the grittiness.

"I'm fine, Mom," he lies. She doesn't believe him, but gives him his space anway. He appreciates it.

"Any particular reason why you dug it up?" she asks carefully. Sam looks at the mess of memories strewn across his bedspread. It was an obvious deduction on his mother's part, but it still startles him. "If you don't want to talk about it, that's fine," his mother adds after a long moment.

Like the coward he is, Sam takes the easy way out.

"Could you tell me about her, your mother, I mean," he changes the subject. "I don't know much about her besides her name and some of the things Dean's told me about when the angels tossed him back in time."

"Of course," she replies, her eyes soft with compassion. They move to the lounge, where Dean finds them two hours later, still reminiscing.

Sam stares at the phone in his hand with the same trepidation typically reserved for live grenades. He can just imagine the conversation.

"Hi Dean, this is Sam," he'd introduce himself, as if Dean wouldn't recognize him.

"...Sammy?" his brother would say in that mix of hope and hurt that always cut him to the core.

"Yeah, man…" Sam would trail off, because none of the usual pleasantries would work with Dean. He couldn't ask 'how are you' because for all he knew Dean was in the middle of nowhere with his guts ripped out by some monster. Or was in the hospital after a ghost had broken his ribs again. Or was in some manky hotel room nursing a concussion or a hangover or both. He couldn't ask 'what have you been up to' for the same reason. Dean would know nothing about current politics or sports or anything that Sam spent days chatting with his new friends about. Dean's life was hunting, and Sam's life wasn't.

"You okay?" Dean would ask after a long moment of awkward silence. He'd ask, because that's what he always asked, because above all else, Dean had to take care of Sammy. But Sam wasn't Sammy anymore and hadn't been for a long time.

"I'm fine," he'd snap without meaning to. "I just…"

"You just wanted to what, huh? Can't help you with your calculus, college boy. You're on your own." Dean's voice would sound teasing, but the words would still cut like the knives in the trunk of the Impala.

"That's not why I called…" Sam would try, but it would be too late.

"Sammy?" Dad's voice would snap through the line.

"Yessir," Sam's mouth would answer before his brain could protest the instinct.

"Enough playing around. You come home. Right now. That's an order." There would be no give in that demand, no forgiveness and no mercy. Sam hates that particular tone with every fiber of his being.

"No," he'd snarl, because if he knew anything, he knew that he was never getting back into hunting.

"Then there's no point to this conversation." There would be a faint protest from Dean in the background, and then the line would go dead.

Sam knows that even if he did manage to get his brother on the line for more than a few stilted sentences, he'd do nothing but mock and tease and belittle him, because that's what big brothers like Dean did. Sam couldn't bear it. Not after so long, and certainly not after the bitter words they exchanged two years ago.

But at the same time, he can't imagine asking a girl to be his wife without first asking Dean how to do it. Dean taught him how to talk to girls in the first place, after all. He taught Sam how to flirt and how to kiss and how to get to second base and how not to make an idiot of himself if he was lucky enough to reach third and how to use protection on the outside chance that some nerd chick was dumb enough to give him a home run. Each of those lessons had been awkward to the extreme, full of unnecessarily graphic anecdotes and lots of appropriately grossed-out noises from Sam, but the gruff brotherly advice had proven invaluable.

Sam knows how to ask Jessica to marry him. He's at Stanford on a full scholarship: he's not an idiot. But the little brother part of him, the part that misses being called 'Sammy', wants to ask his big brother how to make what is arguably the most important decision of his life.

But Sam hasn't spoken with Dean in almost two years now, and their last conversation made it clear that Dean never wanted to speak with him again.

So Sam stares at the phone in his hand with the same trepidation typically reserved for live grenades until Jessica wraps her arms around him and kisses his temple and tells him to stop brooding because dinner is ready.

"So when are you going to get around to it?" Dean asks with his usual lack of antecedents. They're sitting in front of the TV, a bowl of popcorn between them. Eileen is with Jody and the rest of her girls getting their nails done. Sam doesn't really see the point of mani-pedi's when they're all hunters elbow-deep in monster gore most days, but it makes them happy and gives him some time with his brother, so he's not going to ask any questions.

"So when am I going to get around to what?" Sam replies before taking another swig of beer. The 1930's horror film in front of them is as grainy as it is cheesy, the overacted audio turned down to a low murmur in the background. Their TV sessions are never about what's on the screen anyway, never have been.

"Asking Eileen to marry you."

Sam almost chokes on his beer.

"Don't try and breathe the alcohol, dude, it never ends well," Dean says exasperatedly as Sam hacks and coughs. "So I take it that you weren't planning on making her an honest woman anytime soon?"

"Dean," Sam groans in the most annoying little-brother tone he knows. He so does not want to be having this conversation. Ever.

"Sammy," Dean returns in the most annoying big-brother tone he can.

"What, you're looking for a chick-flick moment? Great news: Hell just froze over!" Sam tries to use his brother's tried-and-true method of sarcasm and distraction. Dean raises an eyebrow, clearly seeing through his ploy.

"Fine, be that way," he huffs, snagging a piece of licorice. "But on the off-chance you get your head out of your ass, the formula is: nice dinner, private location, one knee, please."

Sam knows this, of course. He's not an idiot. He almost did it once before, which is why he's never doing it again. Dean takes in his uncomfortable posture in a glance.

"Sam," his voice is quiet, calming. Dean's patented 'big brother's gonna take care of you, everything is going to be fine' tone. Sam's blood pressure drops several points and his muscles unclench instinctively. "Eileen loves you, dude. And you love her. Everyone in this family wants you two to be happy. We're not going to…"

"Don't finish that sentence," Sam snaps more viciously than he intended. He wants to believe his brother's promise that nothing bad is going to happen to them. He really truly does. But he knows his history, and history will always repeat itself if you don't learn from past mistakes. Sam knows that he's not allowed to be happy. Not for long, anyway. When he does, the universe makes him pay for it in the blood of his family. He can't let that happen to Eileen. He just can't.

Dean means well, and Sam knows in his bones that he won't intentionally let him or Eileen come to harm, but he also knows that there is far too much dark and evil in the world. As much as he wants to believe the fairy tale, Dean can't protect them from everything. Sooner or later, the monsters will win. Sam isn't allowed to have the perfect life. Every time it does, it goes up in flames around him. What he has now is too damn close to perfect already. He walks in perpetual fear that any moment everything will come crashing down around his ears.

"I was going to say," Dean doesn't sound like he's upset by Sam's anger, only tired, "that we're not going to force you to do anything you don't want. If you like what you've got rolling, cool. But if you want something more, we'll support it."

Sam shoves some popcorn in his face to avoid having to respond. It turns into over-salty styrofoam by the time it reaches his tongue.

"Oh, and I happen to know from credible sources that Eileen likes low-profile silver rings with colored side stones. And that she'd like to get one from you."

Sam shoves more styrofoam into his mouth and stares at the grainy pixels on the TV like they hold the answers to the universe. Knowing Chuck, they just might.

"And I also happen to know of a hunter who daylights as a custom jeweler," Dean continues, "And I also happen to know that you hate this movie, and that you're purposely ignoring me. That's ok, man. This is scary stuff. Life is scary, especially ours. But wouldn't you rather be scared with someone you trust at your side?"

That makes Sam look over at his brother. But Dean is already walking out the door, promising to fetch more beer and candy.

"Hi, this is Sam Winchester, I'd like to make a reservation for two," he says. He makes sure to use his 'lawyer' voice, all confidence and smartly enunciated syllables. The waiter on the other end of the line takes his details. Making a reservation two weeks in advance is a little unusual, but not unheard of. Sam doesn't want to take any chances though. Two weeks from now, he'll have heard back from his interview. He'll have a future, a way to support them, a Plan. He can already see the house he's going to buy for her, all tall windows and white picket fences. It's a house that Dean would laugh himself silly over if he'd ever saw it. Which he won't. Because Sam is Normal now, and he's not going to risk Jessica by exposing her to that world, however indirectly.

"What was that, baby?" Jessica calls as the door slams behind her. Sam easily palms the phone and plasters an easy smile on his face. He's very good at lying to her, by now. But this lie, unlike the others, rests easy on his heart.

"Spoof call," he shrugs, placing the phone on the counter to free his hands to wrap around her waist. "How was work?"

The familiar smell of diner food lingers in her hair as she stretches onto tippy-toes to kiss him. "The milkshake machine broke again, but thankfully there weren't many people in today. Suzie let me leave early."

"Lucky me," Sam brushes a stray hair away from her face. She's so beautiful, and he loves her so much he can hardly stand it. She deserves better than Sam, with his lies and his history full of blood and monsters. But for some reason she wants him, and so he's going to do everything he can to deserve her love. He thinks of the red velvet box hidden behind the bedpost and smiles.

"You look like a man planning something," Jessica boops his nose.

I'm planning on making you my wife, he wants to say. "Just thinking about what we could do to use up all the extra hours this evening," he whispers seductively instead.

"Oh, I can think of lots of things we could do," Jessica kisses him again before leading the way to their bedroom.

Sam doesn't bother with reservations anymore. Their schedule is so unpredictable as to make the entire exercise pointless. Case in point: two weeks ago they were in Kaibito Arizona hunting a Natackas. Two days ago they were chopping off vamp heads in Omaha Nebraska. Two hours ago they'd just finished cleaning up from an unexpected salt'n'burn in Athol Kansas. Sam's basically given up on planning for the future at this point, but he definitely knows who he wants to spend it with. So, Chuck willing, two hours from now he'll be showing Eileen what's in the new green velour box he's been hiding in his sock drawer.

Sam doesn't really have a Plan for his life anymore. Staying alive and keeping his family together seem to be lofty goals most days. He's made his peace with that, mostly with Eileen's help. She helps him find and relish the joy of spontaneous moments. Just yesterday she'd drug him over to a random farmer's market and forced him to try raw rhubarb dipped in sugar. He'd never tasted anything like it, all sweet and sour and crunchy with an unexpected tang. Sort of like their life together, actually. It's something that he can't quite get enough of.

Eileen buys more rhubarb than he could reasonably eat in a month. And a homemade pie for Dean just because.

She knows the entire alphabet of his story: Azazel, Becky, the Cage, demon blood... And yet Eileen's still here, with him and the rest of his crazy family in the Bunker. He considers it a greater miracle than any one of his many resurrections. Sam keeps no secrets from her, the green velour box in his sock drawer being the singular exception to that rule. Eileen's not an idiot, and she knows that his trips with Dean to various car shows are a front for something else. But she trusts him, just like he trusts her. No questions are asked beyond what they want on their sandwiches as she packs them a lunch for the road.

Saving the world notwithstanding, he doesn't deserve her. If saving equated to ownership, he'd give her the world and it still wouldn't be enough, in his estimation.

"You look like a man planning something," Eileen signs from across the table. Sam looks up from his laptop, hoping his plans for the evening aren't as obvious as the advertisements for honeymoon getaways garishly flashing across his screen.

I'm going to make you my wife, if you'll have me, he wants to sign back. I'm scared shitless because I've never actually gone through with this before, and every time I've tried to take love seriously it ends in disaster. You've more than proven that you can take care of yourself, but I worry. The price of love is the fear of losing it, after all. But you've shown me that I can't let that fear keep me from enjoying what I can have in this moment. "I love you," he makes no sound, only moving his lips because of the sudden lump in his throat. She understands him perfectly anyway.

"That doesn't answer the question," she rolls her eyes in fond exasperation before turning back to her book. She's wearing one of his old sweatshirts, and the baggy sleeves hang loose around her wrists. Hopefully, a very special ring will adorn those slim fingers soon. Sam leans across the table and plants a kiss on her forehead. Eileen tips her head up to kiss him properly.

"Whatever it is you're planning, I hope it includes more of that," she gives him a wink.