AN: Dean/Benny is the ship I wish the show had committed to. I adore them together so I'm having a go at writing a canon-compliant fix-it for them. Enjoy :)

The damnedest thing about Heaven is that he's still not happy. Don't get him wrong, he's not exactly sad either, but even with the alterations Jack made, reinventing Heaven as a better place, he still feels like there's something missing.

He thought in Heaven everyone was supposed to be content, and sitting here at the dinner table in his parents' house, with Sam beside him, he feels terrible for not being satisfied, because this is everything he claimed he ever wanted.

His parents are ridiculously in love, it's funny, and amazing, to see them both so loved up. When he knew them they both seemed too tough to be all giddy about it, but then again his dad did give up everything, centre their whole lives around the fact that he lost his wife. And as for his mom, well this is the first time she's been able to truly be herself, they are both hunters now, there are no secrets anymore.

And then there's Sammy, in life he was married, had a kid and everything, and now he's got Jess. She waited for him, the love of her life, and Sam reciprocates her feelings. Dean isn't exactly sure what that means about Sam's wife, but he supposes there are others in a similar situation, and maybe they'll find each other here in Heaven. He himself never found 'the one' while he was alive, so maybe that means there are still surprises in store for him, maybe someone is alone like he is, waiting, and they'll find each other eventually.

When they finish dinner, Winchester surprise which they don't need to eat, but want to eat and therefore can because Heaven is what you make it, he's standing beside his mom at the kitchen sink, helping with the dishes. Again, these dishes would literally wash themselves, but he likes the domesticity, and the easy moments with her, so here they are.

"Honey," she says, a little more motherly now that they are a complete family again. "What's wrong?"

He freezes, then looks into her sympathetic eyes, suddenly feeling doubly terrible that his discontentment is ruining Heaven for someone other than himself. And in that moment it starts to feel like a hunt, like the hard and demanding life he thought he was done with, he doesn't know if he can go back to feeling like that, he likes it here, the peace of it, how can he make this feeling go away?

"Dean," she says, taking the tea towel from him and drying her hands. "Talk to me. I'm a hunter and your mom, there's nothing I can't handle."

That makes him smile, a small sad one, he loves that even here in Heaven, even being allowed to be crazy in love, she still manages to be a total badass.

"Nothing," he sighs, because it's the truth. "There isn't anything really wrong."

She gives him a thoughtful look.

"Is it you're dad and me?"

"No," he rushes out, the last thing he wants is to ruin her happy ending.

"Let me finish," she says, gently touching his arm. "I mean seeing us together, seeing Sam and Jess, it must be lonely sometimes."

"No," he argues. "Being with you guys is all I've ever wanted."

"That's my selfless boy," she smiles. "But honey, this is Heaven. You don't have to settle anymore. If there was ever a place to have your happy ending, it's here."

He knows she's right, and he doesn't want to be the martyr anymore, he wants what the rest of his family has, except he realises in that moment that it's impossible, what, or rather who, he wants is beyond his reach even here. And because this is Heaven, because it's all about acceptance and peace, he finally just says it.

"He's gone, Mom. He's in the Empty now."

With that one statement he's just gone ahead and told his hunter mother that he's in love with a monster, a dude monster. She gives him a soft smile, no judgement, just sadness that he doesn't have what he wants, then she pulls him into a hug, which he wholeheartedly returns. Having a mom is so good.

"Talk to Bobby," she says softly into his ear. "He's alone at that cabin. You might find you guys have more in common than you think."

He pulls back to search her face, she knows something he doesn't, but she just touches his cheek and gives him another smile. "We're Winchesters, Dean. We always have to fight for what we want. It's who we are, and not even Heaven can change that."

xxx

One of the things he loves about Bobby is that he always has a beer in arms reach. Dean only has one foot on the porch and Bobby's already extending an hand to offer him a bottle. He happily accepts it and takes a seat beside his old friend. He actually became a bit like Bobby as he got older, grumpier and more of a loner. It was just easier like that. Still, they both care deeply about those closest to them, like each other for instance.

For a minute they just enjoy the peace and quiet, looking out at forest, and Baby parked in the drive, sipping their beer, sharing an easy camaraderie.

"What brings you out here?" Bobby quizzes eventually.

"Mom, actually. She said I should talk to you."

"About what?" the older hunter wonders.

One thing he does love about Heaven is that (most of) the anxiety is gone, so he can just say things like they are.

"I want to try getting someone out of the Empty. She said we might have that in common."

Bobby gives him a hard look, scrutinising, and yeah, he does understand this could take a minute to process.

"You're talking about a hunt," Bobby assesses. "Who do you wanna spring from there?"

And here's where he hopes his mom knows Bobby as well as she thinks she does.

"A vampire. I met him in Purgatory. He's a great guy, Bobby. I wouldn't ask if he wasn't important to me."

"Important how?"

"I think he might be my happy ending. Will you help?"

Bobby's silent for a minute, something about this has thrown him.

"I never thought..."

"That I'd fall in love with a dude?"

"No. Well, yeah. I mean kinda, though it's not exactly a complete surprise. What I mean is, I've thought about this, getting people outta the Empty, just never thought it could really happen."

"Since when?" Dean wonders. What monster does Bobby miss?

The older hunter picks at the label on his beer and mumbles.

"Since you told me what happened to Crowley."

Dean raises a brow because that sounds an awful lot like...

"He sacrificed himself for you boys," Bobby says to counter the thought. "I think he deserves better than being stuck there forever."

It's all a lot to take in, but Dean being Dean, he can't help himself.

"As far as I know, the Empty is peaceful. They just sleep. I'm getting Benny out for me."

Bobby gives him a sideways look, trying to be serious, but he cracks and gives into a wry smile.

"Shut up, idgit," he grumbles, giving Dean a playful shove, and Dean can't help grinning ear to ear.

"It's all good, Bobby," he laughs, cracking another beer and settling in. "We're both finally gonna get our happy endings."