While You Were Sleeping – Part I:

Summary: Post Season 8 Finale. Off Canon/AU. Stefan gives Damon the cure, and sacrifices himself to save the town, but Bonnie wasn't able to wake Elena from her slumber and the Salvatore School is actually on the old Salvatore property not the boarding house. A human Damon has to navigate the rest of his life without Elena or his brother; thankfully Bonnie is there to set him back on course. We take a journey through the pivotal moments of their lives as they find that what they have been looking for has been in front of them the whole time.

Song Inspiration: Amen by Amber Run

…

And are those real angels in the magazines?
Oh, is there a heaven?
You'd know now you've been
Are those real stars that hang in the sky?
Or are they man-made, a trick of the light?

Amen, amen, amen

…

2044 – Present Day:

She was nervous. A trill of butterflies floated up into her throat as she stood in front of the door of the boarding house. When Elena woke up from her slumber, she expected to be surrounded by those she loved, that she'd be greeted by her friends, and brother, and Damon. She'd hoped that Bonnie cracked the code, as was able to break Kai's spell and find a loophole, but the absence of everyone led her to believe the worst. She was alive, because Bonnie wasn't. Who knew how much time had passed or where everyone happened to be, but if there was one thing that she was certain of, Damon would be here. His old Camaro was still parked out front.

She knocked three times, and waited.

…

2019 – Twenty-Five Years Ago:

Bonnie spotted him the second she walked in the door of the pub. The whole aura around him was melancholy, which she guessed was to be expected. Less than a month ago, Damon lost his brother, turned into a human, and was fated to spend the rest of that human life without Elena unless it meant the death of his best friend. He didn't have much to be happy about.

She slid into the stool beside him, leaning against the bar as she observed him with concern. "Everyone's been looking for you."

Damon scoffed a laugh. "Well, I haven't moved in…hours, so obviously they haven't been looking hard enough. Where else would I be?" he slurred, slamming back another shot.

"We were kind of hoping you'd come back to the boarding house. It's Elena's birthday. We're celebrating." They had done their best to keep her spirit alive by celebrating her birthday every year as if she was there with them, but this year Damon was hit with the reality that he could spent the rest of his life waiting to see her again.

"So am I." he grumbled, reaching to pour another shot. Bonnie grabbed the bottle before he could, and moved it away from him. "Hey!"

"This isn't healthy, Damon. First of all, you're human now; if you keep drinking like you did when you were a vampire, you'll burn a hole right through your liver. Second…this isn't what she'd want for you. You have to try and live your life without her." She explained softly, trying to reason with him, as she had done many times before. Bonnie seemed to be the only one he'd listen to.

"Oh yeah?" He turned to face her finally, his blue eyes hollow. "Is that what you're doing? Living your life without Enzo?" he spat out sardonically. "Because what it looks like is you're trying to distract yourself by using me as your little pet project."

"That's not what I'm doing." She shook her head.

"Oh it's not?" He glared. "All you've done is babysit me since Stefan died. You aren't even supposed to be here. What happened to Africa, Bonnie? What happened to getting the hell out of this town and doing something you want for once?" He was livid when she told him that she was going to put her trip abroad on hold for the year. Damon watched her put her life on hold for everyone else for far too long.

"Africa can wait."

"Why?"

"Because you need me, Damon. Because you're my best friend, and I'm not about to leave you here when you can barely keep your head above water." She exclaimed knowingly.

He sighed with a roll of his eyes. "I'm fine."

"No, you aren't." He didn't meet her gaze, so she turned his chin, forcing him to look at her. "I know you…just like you know me. You might be able to hide it from Ric and Caroline but you can't hide it from me. So, I'm here…even if you don't want me to be. Because we're all we got. Okay?" she raised her brows challengingly, and despite finding her incredibly insufferable in this moment…he found himself smiling.

"Okay." He shook his head with a roll of his eyes. "God, you just never give up on me, do you?" he added playfully.

"Nope!" She popped the 'p' and graced him with a beaming smile before getting serious. "I'll never give up on you, Damon. Even when you have." She hopped off the stool, pinning him with an expectant look. "You coming?"

Sometimes, Bonnie shook him to core with her words. She was so honest, so pure, that he felt blessed to consider her his friend; grateful to have someone so loyal fighting in his corner. Standing, Damon pulled his coat off the back of the stool, and nodded, following her out.

…

2020 – One Year Later:

Bonnie forced a smile to her face as the guy across from her blathered on and on, trying to impress her with his fancy tech company business. She had come to this bar for a little lighthearted fun; Damon's attempt at pulling her out of her funk, but now she felt trapped. She came to the bar to grab a couple drinks for them, and Rico Suave swooped in to buy them before she could stop him. Then she found herself roped into a conversation she couldn't get out of. She didn't want to be rude, but the guy wasn't letting her get a word in edgewise.

"It's just…" he continued on, running his tongue over his teeth arrogantly. "When you run a company as successful as mine, it's hard to find a moment to yourself, you know? Time is money."

Bonnie was about to respond, but right as she opened her mouth, a large hand landed on her shoulder, and suddenly Damon was standing beside her. "Hey beautiful. I was wondering where you got off to." He kissed her cheek affectionately, before letting his eyes land on the tech company guy. "This guy bothering you?"

"Um…" she started hesitantly.

The guy stood. "If you have a boyfriend, it's something you should probably lead with." He grumbled pushing passed them.

Bonnie sighed in relief. "Thank you. I was starting to think I was going to grow old at this bar." She finished the rest of her drink and pushed the other over to him.

"Knight in shining armour to the rescue." He commented, talking a deep pull on his drink. "You looked like you needed saving."

She nodded tiredly. "Yeah, starting to rethink the whole 'get out there and meet someone' plan. I just keep thinking, even if I do meet someone, will it even last? I mean, how do I even begin trying to explain my complicated life?" She shrugged, a resigned but flippant shrug. "I'm going to die alone."

Damon bumped shoulders with her. "Well, you got me until you do. Because let's face it…I don't think there is a single woman on this earth that can put up with me except you." He teased.

She snorted a laugh. "I barely put up with you. It's more out of obligation than anything." She teased back.

"What?!" He exclaimed, gaping at her in feigned shock. "And here I thought I was starting to wear you down. Come on…" he narrowed his eyes at her playfully. "Admit it. I'm growing on you, aren't I?"

"Yeah!" she plastered on a plastic smile. "Like a fungus or a tumor!" She loved this banter back and forth, and she knew Damon could take it and give it back just as good. This was how they showed they cared…and not many people understood that about their friendship.

He rolled his eyes indulgently. "Yeah, yeah…you joke, but I know you love me." He missed Bonnie's surprised glance as he chugged back the rest of his drink. He said it so nonchalantly, so confidently, she almost had to question if he was right. It's not like they ever said it out loud, but after everything they'd been through, she had to…right? "Come on, let's get out of here. The bourbon's better at home."

Bonnie followed him out silently, blinking as her mind wandered. Of course, she cared about him. He annoyed the hell out of her sometimes and there were days she seriously contemplated wringing his neck, but love – even in the friend aspect, was something she didn't take lightly. She'd had the same small group of friends her whole life, and it only got smaller as time went on. Was Damon a part of the few now? The fact that she'd spent the last two years sitting shotgun while they drove across the country on a 'Mystic Falls timeout' as he called it, told her he clearly made the cut. In fact, the more she thought about it, Damon was really the only person who made the cut. Sure, she was still friends with Caroline and Matt, but Caroline was a mother; she had a whole other life now that included PTA meetings and soccer practice and dance recitals. And Matt was Sheriff/Vampire hunter 2.0, leading the brigade against vampires in Mystic Falls.

Damon was her sounding board, her partner in crime…she chuckled internally as the joke occurred to her; the Clyde to her Bonnie…he was there, day in and day out. She glanced at him as he slipped into the driver's seat beside her, shooting her a half smirk as they drove away…yeah, she guessed she did love him in a way.

…

2021 – One Year Later:

"You're mad." He exclaimed, following her, hot on her heels as they weaved through the crowd of the bar.

"I'm not mad." She yelled back over the music.

Damon rolled his eyes, grabbing her arm just as they reached a clearing near the back door. "You can't lie to me Bonnie. I always know when you're lying." His eyes darted between hers. "What's this about?"

She rolled her shoulders in an awkward shrug, pulling out of his grasp. "It's nothing. It's just…it's late. I want to go home."

"We just got here." He balked at her, confused by her change in mood.

"Then you can stay with…whatever her name is." She gestured in the general direction of the dance floor.

He laughed. "You're kidding me. You're mad about that?"

"I said I'm not mad." She fired back in a sing-song tone and a plastic smile.

"Come on, Bon. So I kissed her, I didn't profess my love for her or anything. Tonight was supposed to be fun; a distraction! You were the one that said Elena wouldn't want me to sit around waiting for her." He exclaimed in confusion.

"I know! And I meant that. But look at her, Damon." She nodded over his shoulder at the girl sitting sipping her drink looking around for him, and he followed her gaze. "Long dark hair, big doe eyes…come on. Is she really a distraction?" Bonnie shot him a look he became very familiar with over the years. It always pulled the truth right out of him.

His shoulders slumped. "Okay, I never said it was a healthy distraction." They shared in a laugh before he continued. "You're right." His eyes narrowed observingly. "But that's not why you're mad."

"Okay fine!" she threw her arms up, letting them slap against her thighs. "I envy you, Damon! Because I wish that I could just throw caution to the wind and do what I want without feeling guilty about it. Because I can't just kiss some rando guy at a bar, or God forbid, have meaningless sex with some handsome stranger! I keep telling myself, 'Why not? Be reckless!' but I can't! And I wish that I could be more like you…" she finished on a vulnerable sigh.

Damon stared at her, stunned for a moment. "Bonnie…you don't want to be like me." He stepped closer to her. "In fact, I wish I could be more like you. You're strong. You don't settle for less than you deserve and you shouldn't." She smiled gratefully, ducking her head. "And for the record…I had no intention of going home with her." Bonnie glanced back up. "Don't look so surprised. We're a team!" he grinned, squeezing her shoulder as he pulled her in, tucking her into his side. "You'd think I'd leave you like that? Plus…my standards are pretty high; I wouldn't be caught dead walking out of here without the prettiest girl on my arm." He teased with a smirk, holding out his arm for her.

She allowed herself a laugh as she looked up at him. "Are you trying to cheer me up?"

"Is it working?"

"Yes." She admitted after a beat, linking her arm with his.

They headed towards the door. "Good. But I mean it. No one in here holds a candle to you." He glanced around. "And I do believe I'm getting death stares from a mean looking biker guy wishing he were me, so we should probably get out of here." He laughed nervously.

Bonnie tossed her head back with a good-natured chuckle. "The infamous Damon Salvatore afraid of a biker? Never thought I'd see the day." She'd seen the guy earlier; trying to eye fuck her from across the room as if it were enough to make her come to him. He was attractive, in a buffed, fully tatted-Sons of Anarchy kind of way…but that was definitely not her thing.

He held up a finger. "Now, hold on. Vampire Damon would have probably ripped his eyeballs from his skull. But this current – very human version of Damon has the common sense not to poke the bear…however, I am resisting the urge to rub it in." He looked her up and down, biting his lip contemplatively.

She canted her head, reeling back. "Oh yeah, how so?"

He leaned down, his lips resting by her ear. "Don't slap me, okay." She could here the teasing in his tone, but was confused about what he was talking about until she felt his hands slowly coast down her sides, and slip over her hips.

His nose nuzzled her jawline, and she felt her eyes flutter closed. It sent a shiver down her spine and he smelled like cologne and bourbon. It had been a long time since she'd been touched this way, and she got so lost in it, she nearly forgot who was holding her. A shaky sigh escaped, and it was enough to snap her out of it. "Ookay…" She breathed with a laugh, resting her palm flat on his chest. "I think you made your point." She whispered, letting her hooded eyes slid to catch the guy that had been eying her all night grab his beer, and walk away with one last glare in their direction.

"Have I?" Came his whispered reply.

She swallowed thickly. "Mhm." When he pulled back, he looked down at her with a self-satisfied smirk. "I think you enjoyed torturing that guy a little too much."

He flashed his eyes at her. "Maybe." He held out his arm for her. "Shall we?"

Bonnie linked her arm through his again, eying him warily. She wondered if he even noticed the effect he had on her or if it went completely over his head. If he did notice…he didn't comment on it.

…

2021 – Eight Months Later:

He watched silently from the kitchen as Bonnie laughed as the guy with his arms around her whispered in her ear. Who the hell was this guy? And why hadn't she told Damon about him?

"Girls please! Um, hello? Damon…I could really use your help here?" Caroline gestured to the kids running around as she was cooking. "Ugh, I could kill Ric! Who works on Christmas?!" She thew her hands up in frustration, before wiping them on her apron.

Damon reached down, and scooped Josie into his arms as she ran past him, resting her on his hip. "The dean of a supernatural school for rugrats like this one." He bopped Josie's nose with his finger making her giggle. "Mystical chaos doesn't stop just because it's Christmas, Care." He grabbed a cookie off the baking sheet before she could stop him. "You should know that better than anyone." He shoved the cookie in his mouth, giving Caroline pointed look.

Lizzie pulled on his pant leg. "What's a rugrat, Uncle Damon?"

He looked down, standing Josie down beside her sister. "Rambunctious little kids that don't listen to their parents." He teased. "Why don't you girls go bug Aunt Bon, okay." They started to run off, but he pulled Lizzie back and whispered to her. "Hey…get me the scoop on this guy. And don't go easy on him." He and Lizzie had a special relationship; there was a mischievousness to her that he related with and she was happy to indulge him. She nodded with a little smirk and skipped off, following her sister.

Damon rose to his full height, and Caroline rolled her eyes with a little shake of her head. "Now I know where that mischievous streak comes from."

"What can I say, I'm curious!" he picked at more of the snacks she was preparing. "I mean, who is this guy?"

"His name is Reginald. I work with him down at the station." She started with a little shrug.

Damon's brows furrowed. "Reginald? What is he, a hundred years old?"

She rolled her eyes. "No but you are. It's a family name. He goes by Reggie." She moved around checking on the turkey in the oven. "And he's really sweet, and she likes him. So be nice."

"How long has this been going on?" he turned his gaze back to Bonnie, watching as the girls played with her.

"Not long. About a month, I guess. They met at Friendsgiving dinner…which you would have known, had you shown up." She shot him a pointed raise of her brow.

"I told you, Care…I don't do Friendsgiving. I have a very specific tradition on Thanksgiving. I get drunk by myself in a crypt and talk to my dead brother." He stated with a forced grin.

The vampire sighed, turning to him with sad eyes. "I miss him too, Damon. We all do. You don't have to miss him alone." She squeezed his arm affectionately. They had grown much closer in the last couple years. He was godfather to her kids, and the only one she could lean on when it came to her pain in losing Stefan. He was the only one that she felt she could break in front of; because as a mother, she spent so much time trying to be strong for them, she barely had the time to hold herself together.

Damon offered her a grateful smile, but the moment passed and he deflected. "How could she like him already; she barely knows him! And what does he know about her? Obviously not that she's a witch, or that she spent four months in a 1994 prison world or even that her last boyfriend was a hundred- and forty-year-old vampire that died tragically in her arms." He hissed in a heated whisper before continuing on a ranting ramble. "He probably doesn't even know that she hates cilantro; like really hates it with a passion. Or that she knows all the lines in 'The Bodyguard' by heart, or that the smell of jasmine reminders her of her Grams. She can't possibly be falling for that guy." He finished with a shake of his head.

Caroline's eyes widened before a bubble of laughter slipped out. She covered her mouth with both hands. "Oh my God. Oh my God!"

Damon frowned, bewildered her by her reaction. "What?"

She turned, busying herself again with cooking in a frantic need for distraction. "Nothing! Absolutely nothing. You're right! Not a lot of people know those things about Bonnie…" her eyes finally met his again. "Just you."

He eyed her wearily, swallowing and shifting his weight. "What are you getting at, Caroline?"

"I'm just saying it's a hard standard to measure up to." She concluded, planting both palms on the kitchen island. "Damon, do you-" She cut herself off and straightened forcing a smile on her face as Bonnie walked in with Reggie in tow. "Hey! I hope the girls weren't too much for you guys."

Bonnie graced them with a smile. "Not at all. We set them up with some games in the living room." Her eyes swung to Damon, who was sizing up her date with zero subtlety. "Damon…" she started nervously. "There's someone I want you to meet. This is Reggie. My boyfriend." She drawled out, shooting him a look that said, be nice.

Reggie grinned, holding out his had for him to shake. "Hey man, nice to meet you. I've heard a lot about you."

Damon's eyes narrowed as he left him hanging for a moment. Caroline was right, he seemed nice enough. He was attractive; lean, maybe a couple inches shorter than he was and his hair was a dirty blonde, cut short and clean shaven – not someone he imagined Bonnie would usually be attracted to. He squeezed his hand back, pulling his lips in a cheeky grin. "Wish I could say the same." He ignored the matching glares that Caroline and Bonnie landed on him. "But I guess it's better late than never. Excuse me." He slipped passed into Ric's office where he knew the good bourbon was, and as he walked away, he could here the chatter in the kitchen.

"Well, that went worse than I thought it was going to." Reggie chuckled nervously.

"Honestly…that's exactly how I expected it to go." Bonnie said on a sigh. "Don't take it personally, he's just…being Damon." She tried to explain, squeezing his hand. "I'll be right back." She followed Damon out leaving Caroline and Reggie alone.

There was a moment of awkward silence before he finally spoke up. "Did they…use to date or something?"

Caroline laughed out loud. "No! Definitely not. It's just…their friendship is sort of…complex."

"How so?" he asked curiously, but with genuine interest.

The blonde bit down on her lips as she picked her next words carefully. "It's kind of a long story, and not really mine to tell, but they sort of went through hell and back together, and since then they've always looked out for each other."

Bonnie leaned on the door to the office crossing her arms, seeing Damon looking out the window at the snow falling with a drink in his hand. "You know, you could have just tried to be nice. I mean, not that I'm surprised, really. That's just classic Damon." She said deadpanned.

He didn't turn around as he brought the glass to his lips. "Why didn't you tell me about him, Bonnie?"

She rolled her eyes as she pushed off the wall, stepping further into the office. "Can you blame me? Every guy that I even think about dating you rip apart before I can even get to know him." He turned around to face her finally. "I'm trying to get on with my life, Damon…I can't keep loving a ghost forever, but how am I supposed to move on when you scare them off before I get the chance!" She exclaimed throwing her arms in the air.

He blinked in confusion. "What are you talking about?"

"I'm talking about Ethan, and Jackson…Lawrence?" she listed them off, raising her brows at him challengingly. All guys she was just starting to like when Damon swooped in a ran them off. He may not be a vampire, but he was still intimidating. "God! You talked me out of dating him before you even met him. Why? Why are none of them good enough for you?" She demanded.

"Because none of them are good enough for you!" he fired back heatedly, causing her to reel back. "Can you really be happy with someone like him, Bonnie? Without him knowing who you are, or what you've been through? What you're capable of? People like him aren't from our world, Bon. They don't understand, and they never will…can you really live like that? Holding back a part of who you are?" He asked her seriously, his eyes darting back and forth between hers as he waited for her to answer.

She was stunned into silence for a moment, her mouth dropping open. "What other choice do I have?" she said in a sad strained voice. "I've done the big epic love thing Damon, so have you…and we both know all too well how that ends." She shrugged helplessly, and she could see him deflate and drop his head in agreement. "So maybe, this is it." She stepped forward wringing her hands. "Maybe I don't get to have that again, and yeah, I hate that I can't be honest with him, and every time something comes up, I'll have to lie, but what's the alternative? Tell him the truth and watch him run away scared or end up dead because just knowing about the supernatural is enough to put him in danger?"

Damon rolled his eyes skyward. "If he runs away scared, he doesn't deserve you anyway. You should be with someone who challenges you, who is going to stand by your side and fight with you when things get tough. Who's not going to bail when you're looking death in the face." He pointed towards the kitchen across the house. "Is he that guy, Bonnie?" he demanded of her passionately.

Suddenly she felt panicked, and the air escaped her lungs as she struggled collect her thoughts. No. The voice in her head answered immediately. Blinking, she turned her head away, wrapping her arms around herself. "I should get back."

"Bon…" he tried to call her back as she left the office, but she didn't look back.

…

AN: Happy New Year everyone! I'm back with a longer song story that I have been working on for some time now. I didn't realize how developed this story was going to be until I found myself 30+ pages in after 2 days lol. So, these chapters will be longer than usual, and it will be a multi-part series.

Hope you enjoy this one. Please let me know what you think! - Vanessa