Chapter Seven: Caught Between a Rock and a Hard Place

Bonnie and Sam crept around the perimeter of the main floor, and she used her magic to avoid detection while Sam stealth-killed the demons guards. The two of them worked their way closer to the voices, and Bonnie had to hold back her gasp when she saw Dean beaten and on his knees. The hitch in her voice was enough to draw Sam's attention and she desperately grabbed his arm to keep him from rushing forward.

"Sam…" she hissed. "There's too many of them."

"She has my brother, Bonnie!" he whispered back heatedly.

She nodded in understanding, eying Hope who was currently stalking her prey hungrily. "I know…but if we run in guns blazing, you both die. We need a distraction."

As if she conjured it herself, the door creaked open obscenely, drawing everyone's attention. "Is this the Horowitz bar mitzvah?" Damon announced loudly strolling in casually. "No? Hm." Bonnie smiled to herself at his antics.

Dean's brows furrowed looking around for an escape, and in the shadows of factory, he spotted his brother sneaking around to get closer and a part of him sighed in relief.

Lilith canted her head in annoyance. "I killed you."

"Well, that's the thing about vampires. We take a lickin' and keep on tickin'. Gonna need a bit more than a snapped neck to take me down." He looked her over. "My, how you've grown."

She huffed. "Drexel!" She yelled out. "Get over here!"

Damon pointed behind him. "Oh, was he your door man? Sorry, but he met the point end of this a few minutes ago." He held up the angel blade tucked up the sleeve of his jacket. "Him along with…all your other guard demons." He boasted cockily, flipping the blade between his fingers.

Lilith's eyes narrowed into thin black slits. "They were useless anyway. I have a bigger ace up my sleeve."

Damon smirked. "So do I."

A resounding thud echoed and swayed the building; the sound occurring again and again, louder and faster. Castiel, breaking the warding. They all staggered as the ground shook beneath them before the magical sigil's vanished in a flash.

"What the hell?" Lilith breathed.

Bonnie took the moment of distraction, and whispered a spell, painting Lilith into a Devil's Trap. She held out her hand, chanting as she did, bringing Hope to her knees clutching her head in pain; just long enough for Sam to secure the witch enabling chains on her wrists. She didn't miss Dean's bewildered glance in her direction.

"Bonnie?" Castiel appeared in front of him, eyes hard and determined. "Wait!" And without hesitation, his hand landed on Dean's shoulder, teleporting them out of there.

.

A second later, Dean found himself in the motel. "No! What the hell is Bonnie doing there?!" He yelled, pushing away from Castiel. "Send me back!"

"No." the angel grunted resolutely.

Dean rounded on him, furious. "Damnit Cas! We need to go back for them! She has no business being in this mess."

"Bonnie Bennett is a powerful witch. She can hold her own. My duty is to protect you, Dean." The Angel vowed strongly. "Let me heal your wounds."

Dean stepped back and kicked a chair across the room. "No! You go back and get them, Cas…or so help me God." He threated, glaring down at the angel with fury in his eyes. He blinked and Castiel was gone.

"It's over Lilith." Sam affirmed, gripping the demon blade tightly in his hand.

Damon crossed to Hope, lifting her effortlessly in his arms as she struggled weakly. "We need to get her out of here." He whispered warily.

"I'm not leaving Sam." Bonnie vowed firmly.

"This isn't our fight, Bon." He hissed in frustration.

She turned a hard glare to him. "I don't care. Go. Take her back to the school; we're right behind you." He zipped out of the factory, leaving the three of them behind.

Lilith's eyes narrowed at Sam with a cock of her head. "Is it?" The building shifted again; the foundation now compromised. Her eyes subtly darted to the crack in the floor…running through the barrier holding her hostage. She sucked back the smirk.

"You've lost your impossible beast, your hunters. You can't break the seal. We won." He stated vindicated, closing the distance between them, standing just outside the trap.

The laugh that left her mouth was haunting, and off-putting. "Oh Sammy…" she started condescendingly. "The good guys never win. You may have stopped this seal…but as we speak, another one breaks. I always have a plan b." She laughed again, manically and unhinged. Bonnie circled, fortifying the trap with her magic, but she got too close and Lilith snatched her by the throat holding her in the air. "You think you can out smart me little one? I am always one step ahead."

Sam lunched forward, stabbing her in the back, thrusting the demon blade as deep as it will go. "Hard to be one step ahead if you're dead."

She released Bonnie, gasping through the blood filling her mouth, but her laughter continued. "I did it…" She swayed dropping to her knees.

Sam glared down at her. "Did what?"

Lilith looked up at him, eyes wide in amazement. "The last seal."

Sam blinked in confusion. "What the hell are you talking about?"

The life was leaving her slowly and she spoke breathlessly. "It was always down to you and me Sammy. 'And it was written,'" she began to recite. "'When the first demon dies, the final seal shall be broken.'" And in punctuation, the ground beneath her cracked, and her blood seeped through. "He hath risen." She declared in her final breath.

The ground beneath the continued to crack and break, the building becoming unstable. Bonnie tugged on Sam's arm, as he stood there stunned in realization. "Sam, we got to go. Now."

"Lucifer…"

"I know…but this place is gonna come down." She glanced around them as the stairs collapsed. "Sam…" she begged.

Castiel appeared between them. "We have to go." With a hand on each of their shoulders he teleported them out of the crumbling building.

When they walked in, Dean shot to his feet, sighing in relief as they both looked unarmed. He wrapped his arms around his brother tightly, meeting Bonnie's eyes over his shoulder, shooting him an awkward wave. He pulled away from Sam. "Are you two okay?" His gaze lingered on her, waiting for her to nod in approval. "Lilith?"

"Dead." Castiel confirmed.

A ghost of a smile split his face. "Well, that's good right?"

Sam huffed. "Not exactly. Her death was the final seal."

"Lucifer is free. But's he's weak. He'll be searching for a vessel." Castiel advised solemnly. "I must return to heaven and warn the others. You know how to find me." He was gone a second later, leaving them alone.

Sam noticed the tension between his brother and Bonnie. "I'm gonna call Bobby." He slipped out the front door, leaving Dean and Bonnie in an awkward silence.

"Are you okay?" Was the first thing he asked, regarding her with worry. The back of his knuckles pushed the hair off her shoulder, exposing the finger-shaped bruises on her neck.

Bonnie smiled. "I'm fine. You, on the other hand…" she trailed off, gesturing to the deepening purple-blue bruise under his eye, the bloody gash on his hairline and the cut across his nose.

He shrugged it off. "Oh this…this is just another day at the office." He chuckled, cracking a smirk. "So…you're a witch. Didn't see that coming." Dean chuckled as he eased himself to sit on the edge of the bed gingerly, reaching back into his duffel for the first aid kit.

Bonnie sat next to him, taking the kit out of his hands and focused her trembling fingers on opening it to distract from what his proximity did to her. "I guess we're both full of surprises." She glanced up at him pointedly with a teasing tone. "It all makes sense now; why you left…the whole mysterious bad boy persona. Who knew, you were running around killing monsters and saving lives." She dabbed the cloth with alcohol, and began cleaning the blood from his face. It was incredibly hard to concentrate when he was looking right at her, studying her lips, and the colour of her eyes so intensely.

"It's the family business." He smirked. "Is that why I was so crazy about you? Some teenage love spell?" he joked, but there was a tinge of insecurity in the deep rumble of his voice.

Bonnie breathed a laugh, meeting his gaze. "No…I didn't even know I had powers then."

"How did you even get wrapped up in this life?" He tried not to wince when the alcohol penetrated his wound.

With a deep sigh, Bonnie explained. "My friend. Elena." Her lips quirked in a sad smile. "She fell in love with a vampire and well…chaos ensued." She joked.

"Naturally." He added, watching her reactions curiously. "Something tells me it didn't end well for her…did it?"

She averted her eyes. "No, it didn't."

"Nobody warns you how hard it is." Dean mused thoughtfully. "I mean, you think you know when you sign on for this what there is to lose but…you don't really know until you do." There was a heaviness in his tone that made her feel like the burden wasn't only hers to bare. "Who did you lose?" he asked softly. Dean knew the moment he saw her that she'd been changed by death. Not because she wore it on her face for all to see, but because she didn't. She hid it under a mask; wore it like armor, much like he did.

Bonnie's eyes misted. "My grams. My dad…a lot of friends." She swallowed, fighting to stop the tears that pooled. "The man I loved…" she released a shaky breath. "Never gets easier."

Dean frowned empathetically, catching the tear with the pad of his thumb. "No, it doesn't."

They separated quickly when Sam barged back in and Dean snapped a glare in his direction. He winced, realizing he just broke a moment. "Sorry…but the Sheriff called. Wants us to all meet at the school; figure out a game plan."

Bonnie shot to her feet, somehow both grateful and irritated at the interruption. "Right." She scratched her forehead nervously. "Yeah, okay." She didn't know if the nervousness was because the literal devil was loose, or because Dean and Damon would have to be in the same room, but either or both filled her with an uneasy feeling. "Let's go."

Dean knew that his conversation with Bonnie was far from over. She was able to fill them in on some of the backstory on the way over, but he still had a lot of unanswered questions rolling around in his head. There was a moment when he glanced in the rearview, observing her quietly while she ran her fingertips over the familiar leather of the backseat with a nostalgic smile. Then, as if she felt him, she glanced up and caught his gaze and he could have sworn he saw her blush. That was a great night. He winked at her, and he was certain he saw her cheeks flush.

When they pulled into the driveway, he was a little disappointed to see who was waiting for them, rather impatiently, and with hard blue eyes, leaning against the brick pillar by the front door.

Bonnie hopped out first, and Dean watched as Damon straightened when she walked up, running his hands over her shoulders, looking at her with concern. "We working with vampires now, Sam?" he grunted.

"He helped us, Dean. And the way Bonnie tells it, he does his part to keep this town safe. I think we at least owe the guy a chance." Sam shrugged, getting out.

Dean stayed in the car a moment longer, lip curled in distaste at how close they appeared to be. With another grunt, he got out, walking around the front of the impala.

Bonnie put some space between them, sucking in a deep breath to calm her nerves as Dean approached; standing tall, his hands shoved in his jacket pockets. "Guys, this is Damon."

The two of them stared each other down for a long moment, before the younger Winchester had to ease the tension. "I'm Sam. This is my brother Dean."

The vampire's eyes narrowed. "We've met."

Dean crossed his arms with a disbelieving scoff. "I think I'd remember that."

"Not if I didn't want you to." He barbed back with a lopsided grin.

Bonnie slapped his chest hard with the back of her hand, although her target remained completely unaffected. "Okay! We should get inside."

She was a few strides ahead with the vampire, and Dean followed cautiously with his brother. "I don't like him."

"Yeah, well he doesn't seem to like you either." He chuckled good naturedly, letting his gaze roam the walls full of historic art and supernatural relics.

Dean leaned closer to his brother, analysing the competition. "I mean look at this guy; the gaudy ring, the leather jacket, the v-neck…" he scoffed. "What a dick."

"This dick, can hear you, you know." Damon glanced back over his shoulder nonchalantly with a smug smirk. "Vampire hearing, remember?" They stopped at the end of the hall and he gestured for them to proceed into the parlor room. The mood at the school was somber. In addition to the Sheriff and Alaric, there was also a blonde, who the brothers found vaguely familiar.

Bonnie nodded at them in encouragement. "I just need a minute. Make yourself comfortable." When they walked down the steps and into the sunken room, Bonnie fixed him with a look.

"What?" he played innocent.

Her hip cocked out and she crossed her arms, all in one fluid movement. "I can feel the hostility. Play nice, okay."

He laughed. "Wha-I am!" he defended, not sounding genuine at all. "He was the one that called me a dick, why don't you tell him to play nice."

She pinned him with a deadpanned stare. "You are a hundred and eighty-one years old. Can you be above the 'he started it' defense, please?"

He leaned closer to her. "Sorry, I'm not exactly thrilled to suck up to your ex-boyfriend, Bonnie." He whispered heatedly.

She rolled her eyes. "I'm not asking you to. Just…be civil." She skipped down the stairs towards Caroline, who wrapped her up in a hug. "Hey. How's she doing?" the witch asked, shoving her hands in her back pockets.

"The same." Caroline sighed. "I had hoped that I could get through to her with this." She held up a journal. "Freya said she found it in Hope's old room, but she didn't go for it. Damon has her dosed up in the cellar." The blonde squeezed her hand. "Are you okay?"

"As good as I can be, all things considered. I have a lot to fill you in on." Bonnie sighed tiredly.

Caroline's eyes looked passed her to the two guys looking around the parlor, one pouring themselves a drink and the other perusing the bookshelf. "Who are Tall and Handsome over there?" she whispered with a flirty flash of her eyes.

Bonnie couldn't stop the indulgent eyeroll. It was just like Caroline to find the silver lining in a time like this. "Sam and Dean Winchester, remember them?"

"No way!" She exclaimed, slinking closer conspiringly. "Wasn't Dean, like the first guy you ever-?"

Bonnie hushed her embarrassedly. The words were barely heard by anyone around them, but to her, it sounded like her friend shouted it from the roof tops. "Seriously?" She hissed back, risking a glance back to see the brothers talking to Matt. "They're hunters." Caroline's back went up defensively. "Don't worry, they're on our side."

"What the hell happened to you?" Matt asked Dean curiously, on the other side of the room.

Dean forced a grin. "Well, I got used as a personal punching bag. I'd say, you should see the other guy but…she's dead."

Matt and Alaric's brows shot up in surprise. "Lilith's dead?" The Sheriff asked.

Sam nodded, albeit somberly. "Yeah…but we didn't stop her from breaking the final seal. Lucifer is free." He kept his gaze down, wearing the weight of his guilt heavy on his heart. His lips quirked when Dean squeezed his shoulder reassuringly. "But your friend…she's not under her control anymore." He added with a bit more optimism.

Alaric swallowed. "So what do we do now?"

"We kill Lucifer, that's what we do." Dean declared.

Damon scoffed, as he came down the steps. "Sure, no problem! I'm sure that'll be a walk in the park." He stated with a sarcastic grin.

Dean threw daggers his way. "You got any better ideas?"

"We are talking about Lucifer; Satan, the Prince of Darkness." He explained dramatically with a lazy roll of his eyes. "You're telling me a couple of hunters are enough to quake him in his boots? Please." Damon drawled cynically. He snatched another glass off the bar, pouring a full drink and tossing ¾ of it back.

The older Winchester's jaw tightened. "So what, you gank a couple demons and suddenly you think you know a thing or two about the hell we fight everyday." It was taking everything in him to keep his voice even, not wanting to ruffle feathers in this unfamiliar environment. But he was also unwilling to back down.

Damon's sauntered over, a hard glare in his eyes. "No, but I've got a few years on you, boy. And he's got, I don't know, a millennia more. I think you're out of your league."

"Guys!" Bonnie crossed the room quickly and stepped between them, a hand on each of their chests as they stalked towards each other. "We are all out of our league." She began to defuse. "But maybe if we do this together, we stand a chance." She felt them both deflate slightly at her touch. "Okay…"

They spent the next hour covering everything they knew, the weapons in their arsenal and what their options were.

"And we have Cas." Dean began, leaning forward and resting his elbows on his knees from his spot on the couch. "He's an angel, probably the closest match to Lucifer's power."

Sam mimicked his brother, rubbing his palms together. "What about your friend, Hope? I mean, she's a tribrid, she must be fairly powerful." He offered gently.

"She is!" Caroline confirmed. "But she couldn't care less about helping us; not without her humanity."

Dean nodded. "And how do we go about fixing that?"

"Torture, usually, or starvation." Damon piped up from his spot standing next to Bonnie. He swirled the booze in his glass casually. "Both of which we've tried."

Bonnie swung her eyes to Damon with a glare. "We need to trigger an emotion. Damon seems to think that pain and anger is the way to go-"

"Because it works." He interjected.

The witch ignored him and continued. "But I think her dad is the only way through to her. They were very close." She added regretfully.

Sam frowned. "Niklaus Mikaelson? The Hybrid, right? Isn't he dead?"

"Very." Damon tossed back the rest of his drink.

There was a tense moment while Dean thought hard, his brows furrowing, the wheel turning in his head. He shared a glance with his brother, and Sam nodded in silent agreement. "I think we can help with that." He voiced confidently.

"Time travel?" Alaric clarified, both doubtful and curious.

"Angels, as far as we know are the only ones capable of it." The younger Winchester began to explain.

"Hm. Back to the future rules?" Damon questioned; a brow quirked. He couldn't believe they were actually entertaining the thought of going back in time with two humans and an angel – it sounded like some unbearably tongue-in-cheek sitcom.

"No, what you do there doesn't change our present, but it's best to interact with as few people as possible." Sam responded seriously, as if it was a legitimate question to ask.

Caroline bit her lip apprehensively. "Have you done it?"

Dean's gaze swung to her. "I have. And it's a trip. Fair warning, go on an empty stomach."

"And Castiel will do this for us?" Bonnie asked worriedly.

He offered her a gentle, reassuring smile. "If it means stopping Lucifer, Cas will do anything. Plus, he owes me one or two." He finished with a lazy wink.

"Not everyone can go. But whoever does needs to be able to explain to Klaus what you're doing there. Someone he trusts." Sam put out to the group, observing how they all ended up looking to Caroline. "I assume that's you?"

Her eyes rolled, as she crossed her arms. "We hooked up once, like a hundred years ago." With a defeated sigh she caved. "But yeah, I suppose it is. What do I have to do?"

Sam went over the rules with her, while Dean prayed to Castiel. It wasn't long before he popped out of nowhere, catching the others completely off guard.

"Hello Dean."

Dean turned around his eyes landing on the Angel. "Cas…we have a shot at stopping Lucifer, but we need your help."

"Of course. What did you have in mind?"

Across the room, Bonnie watched Dean speaking with Castiel, unable to look away. The way he took charge and jumped into this fight headstrong and fearless was admirable and really attractive. She had to wonder what he'd been through for him to be so dauntless when facing evil. She remembered the flashes she saw during their kiss, and the pain she felt as if it was her own.

Damon slinked up beside her silently, making her jump when he spoke. "Are you cool with this?"

"With what?" she pulled her gaze away to face him.

"Caroline doing this…without you." He said knowingly. He knew Bonnie; he knew that she would do anything to protect her friends from danger, and having to sit this one out was probably killing her.

She released a huff. "She can handle it. And Sam is right. It needs to be someone that Klaus will trust. Caroline is the only one he'd listen to."

"And Dean?" Bonnie snapped her head to him. "You trust him?"

She could tell where this was going. "Yes. I know you don't like him-"

"Like isn't the word I'd use." He interjected bitterly.

"But he means well. And so does Sam." She continued over him. "They didn't have to help us, Damon. With Lilith or with Hope…but they did. Why can't you give them a chance to prove you wrong?" She tried to sway him gently.

His blinked, like the answer was obvious. "Because people like them get dead fast. And so do the people around them." He finished, meeting her eyes pointedly. There was a time that he would have included himself as one of those people. Back when he would shoot loose and from the hip, charging in guns blazing and the consequences were at someone else's expense. Too many times it had been someone he loved; Elena, his brother, Ric, Enzo…Bonnie. Done were the days where he would ever allow her death on his watch. "They are children running around playing hero in a game where they are rigged to lose. They might as well both be wearing an 'I'm with stupid' t-shirt." He snarked glibly. It was the only way he knew how to cover the very real concern he was feeling.

Bonnie of course saw right through it, and squeezed his arm warmly. "You're worried. I know, but you can't protect me from everything. And I believe in what they do. They save people's lives. Everyday. No thanks, no glory, no light at the end of the tunnel. So maybe to you it's stupid, but…I think the world needs people like them." She stated with a soft smile.

Damon was lost in thought for a moment, but when he saw her about to walk away, he zipped in front of her so she ran right back into his chest. "I agree." He swallowed, letting his eyes roam over her face, worry clear in the blue depths of his eyes. "I just don't want that person to be you. I can't lose you, Bon…but I can't stop you either." His lips curled in a crooked smirk. "God knows, you're as stubborn as a mule." It made her chuckle, and the smirk turned into a smile. His finger delicately pushed a strand of hair out of her face. "Just be careful, okay?" The words came out just above a whisper; only for her to hear.

Bonnie was sure he could hear her heart hammering in her chest. It was impossible to hide it when Damon showed such tenderness towards her. Many years ago, she wondered what Elena ever saw in someone she had known to be so callous, but this Damon…this Damon was easy to fall for. He'll make you want to bend your morals and throw caution to the wind and get swept away with the current; anything to have him keep looking at you like you were only woman on the planet. She nodded with an affectionate smile. "I will."

Sam and Castiel were talking now, but Dean couldn't help but tune them out. His mind was directed elsewhere, just passed them between their shoulders where Bonnie was having a hushed conversation in the corner of the room. He hated that it bothered him so much, seeing her with him, knowing he had a part of her she might never give to anyone else. It was clear on her face and his that there were some unresolved feelings there, and maybe if it were anyone else, Dean would have been able to just walk away, claim she was better off and say Adios as usual. But he couldn't.

"Dean?" Sam asked.

"Yeah." He answered back but his eyes never strayed.

His brother looked at him expectantly. "What do you think?"

"Sure." Dean clapped him on the shoulder. "Whatever you think is best." He slipped between them crossing the floor to Bonnie, ignoring when Damon rolled his eyes and turned away. "Hey Bonnie." He started keeping his eyes on her. "Can we talk?"

She sucked in a breath, shoving her hands in her back pockets nervously, risking a glance at the vampire, who was clearly bothered by the interruption. "Yeah, yeah of course." She led the way out towards the kitchen to the back porch, settling into the porch swing, her fingers gripping the wood on either side of her thighs. "This is more…private."

Damon can't hear us is what he gathered. Dean eased himself down beside her, releasing a heavy sigh as they both took a moment to enjoy the silence of the night. "You two are pretty close, huh." He questioned keeping his gaze on his hands, brushing his palms together. He really didn't want to know the answer, but the words came out anyway.

"We've been through a lot. He's been my best friend for a long time…my enemy before that. There was a time when Damon was my only friend." Where did she even begin to explain her relationship with one Damon Salvatore? They were friends, but they were also more than that. They hate each other sometimes, but loved the other anyway; constantly teetering on the edge of something or nothing. "But we aren't together, if that's what you're asking." She risked a glance back up at him.

He chuckled almost embarrassedly. "It was." He admitted honestly, shooting her a charming smile. "I'm not really known for being subtle." His brow furrowed and his tone became more serious. "Bon, when we kissed…" he turned his head to her nervously. "What happened? I mean, you ran out of there so fast…"

The question caught her by surprise, making her blink as she recalled the flashes that seemed to burn in her mind. She visibly cringed, hearing his screams echo in her head. "I had a vision. At least that's what I think it was. I saw you…in pain; being tortured." She swallowed, the feeling of it still fresh behind her eyes. "And a woman…she was on fire, on the ceiling." She whispered, watching as Dean seemed visibly shaken by her admission, running his hand over his mouth, before resting his fist against it; his knuckles white with tension. "What was that, Dean? Was that real?"

He nodded swallowing the emotions thickly. "Yeah. That was my mom." His voice cracked, and he cleared his throat. "That's how she died. Sam was just a baby."

Her heart clenched, and her hand went to his knee comfortingly, her body unconsciously sliding closer to his. "I'm sorry." She chose not to tell him about the end of her vision, of her in his mother's place. That would only worry him further. "What happened to her?"

He released a heavy sigh. "She made a deal with a demon. And when he came to collect, she tried to stop him. That's how my dad found her, and ever since he's been hunting down the thing that killed her. Until he died."

"And what happened to you?" she questioned softly. She felt him tense under her palm. "It's okay…" she promised with an encouraging but watery smile.

"I was in hell. Here, it was only about four months but there…" A deep frown pulled his brows. "It felt like eons. Every day, I was carved into, tested…they wanted to break me." He found that it was almost cathartic telling Bonnie the secrets he kept to himself. He'd always wanted to; to open up and let her in, show her the person he buried in humor under the tough guy exterior. But he knew he could never be selfish enough to pull her into this world. "Told me all I had to do to get off the rack was to torture souls, like I'd been tortured. And I held out…for thirty years, I fought it. But then one day…I just couldn't anymore. I gave in." A tear fell unchecked down his cheek, and Bonnie felt her eyes welling up at the pain in his voice. "And it's what started all of this." He looked at her then, his golden green eyes seeming brighter with the unshed tears brimming. "'The First Seal shall be broken when a righteous man sheds blood in Hell. As he breaks, so shall it break.' I started this. That's why I have to finish it." He concluded firmly, with resolve.

She recognized that determination; the feeling of being responsible for the pain caused to the people around you. The weight of the world on your shoulders and the guilt for the blood on your hands. "I'm here for you. This isn't something you have to deal with on your own."

He scoffed ironically. "I always have. I always felt like I had to carry this burden alone growing up, for Sam. To protect him. I never thought I'd be able to talk to someone about this, you know, to someone that would understand…" he let his eyes roam over her face with a tender smile. "You make it easy, somehow." His hand covered hers on his knee, bringing it to his lips to kiss her knuckles. "You mean a lot to me, Bonnie, you always did. I hope you know that."

Tears welled in her eyes. "I do. You mean a lot to me too, Dean. You know that feeling…" she averted her eyes sheepishly to watch his thumb caress the back of her hand. "When you feel like you're forgetting something, but you can't remember what?" She let out a shaky breath, meeting his penetrating gaze. "I've felt like that for a very long time. But seeing you again…I feel like I'm starting to remember." Her teeth worried her bottom lip.

Dean's eyes dropped to her perfectly pouting lips. She was so close. "And what's that?" He asked her in a raspy tone, that made her mouth run dry.

Just as she opened her mouth, the door opened, and Caroline popped her head out. "Hey guys…Sam is asking for you." Dean stood first, leaving Bonnie with a secret smile and letting her hand slip from his. Caroline waited until he went back inside. "Sorry, I didn't mean to interrupt." She uttered apologetically. "But if I didn't come out Damon would have." She added pointedly as Bonnie rose to stand in front of her. "Have you talked to him yet?"

The witch dropped her gaze to the wooden deck, shifting her feet anxiously. "No. One crisis at a time, okay?"

"Bonnie…" the blonde admonished. "He deserves to know."

"I know that. But, I can't…not right now." She knew doing so would open another can of worms that she wasn't prepared to face. "Look, when we get Hope back, I'll tell him. I promise." She changed the subject. "Are you ready for this?"

Caroline scoffed with a flick of her hair. "Oh, you mean going back in time to convince my dead hybrid lover to trigger the humanity of his out-of-control teenage tribrid? Oh yeah! Totally ready." She babbled sarcastically.

"How far back are you going?" She knew this wasn't an easy task for her friend. Despite everyone else's issue with him, Bonnie knew that Caroline had a soft spot for him in her heart, much like he did her.

"Um…the last time I saw him I guess." She breathed reminiscently. There was a lot she had wanted to say then that she wish she should have in retrospect. "Is it weird that I'm nervous?"

Bonnie shot her a reassuring smile, running her hand up and down her friend's arm soothingly. "Not at all. Just be careful, and bring our Hope back." They shared a tight hug before joining the rest of the group in the parlor room.

"Okay!" Caroline let her hands slap the side of her thighs. "Let's do this!"

AN: Alright! Next chapter is going to be fun to write. We're going back in time, sitting shotgun in a couple flashbacks and some more Damon and Dean confrontations! I'm really looking forward to shedding light on Bonnie and Dean's relationship back in high school. Also…any ideas on what Bonnie needs to tell Damon? Excited to hear what you think!

Vanessa