Caroline

"Five... Four... Three... Two... One! Happy New Year!" The entire party erupts all around the back yard at the Lockwood mansion, fireworks go off and kissing ensues. Laughing I turn to look at my boyfriend Tyler Lockwood the host of tonight's New Year's Eve party and I freeze. He's down on one knee, black velvet square box popped open with a square cut diamond sparkling in the center of the box. My breath hitches, oh God, oh shit! "Caroline Forbes, we've been dating since our Freshman year in high school, I knew it then and I know it now... I want you to be mine forever, I love you Care and we may be graduating high school in a few months and heading off to college, but I can't go another day without being able to look on your finger and seeing this ring. Please make me the happiest guy in the world and say yes to marrying me. I know it's sudden and in no way am I saying we have to get married next month or even next year... just say yes because I love you and want a life with you Caroline." Everyone around us is looking, oohing and ahhing, now all eyes are on me. Waiting for my answer, Tyler raises a brow as he thrusts the ring box upwards towards me and I release a breath and slap on smile. "Well of course I will! Yes Tyler! Yes, I'll marry you." Clapping and whistling ring out and then there's this cold weight on my left-hand, ring finger, looking down at the diamond I blink and smile but then I'm wrapped up in my boyfriend's, no fiancé's arms and he's kissing me.

I'm shaking to pieces; he chuckles leaning his head back. "Got kind of worried there for a minute and thought I was making an ass out of myself." A forced laugh bubbles up from my tightly closed throat. "Had to make you sweat it out for a second." A smirk comes across his face as he kisses me again, I'm still shaking and he runs his hands up and down my arms thinking he's warming me up, truth is I'm on fire and the shakes are from pure horror of what I've just agreed to. But this is what I've wanted forever right? To fall in love with my high school sweetheart, get engaged and married to him then after a career is established start a family? Yes, that's exactly what I wanted, but... do I really want it with Tyler? His mother Carol makes a beeline for us, she's all smiles and the Martini glass in her left hand sloshes over and pours down my back once I'm being crushed into her hug. "He's been waiting since Christmas to propose tonight, congratulations honey and welcome to the family." My throat is closing again, I simply nod at her and then she's downing what's left of her drink before going to her son. "I can't believe this! Care you're getting married!" Grinning I turn around looking at my best friend from childhood Elena Gilbert, her boyfriend and Tyler's best friend Matt Donovan has his hand wrapped around her slim waist. She pushes a strand of her long brown hair behind her ear and snatches me over and into a hug. "Breathe Care, just breathe." A nervous giggle escapes me, then I hold up my hand lamely. "It's a beautiful ring, he did good." She says offering a smile, she knows me well obviously and her look says, 'we will be talking in depth about this later'. Matt snorts peering over to catch a glimpse of my ring, "More like mama Lockwood did good, then again she'll only want the best for her family." Elena and I both laugh and smack Matt, but he's not wrong at all. Carol Lockwood is all about the Lockwood family name and having the best means being the best and yeah... it's exhausting being around her and now I just sealed myself as her future daughter in law.

Hands land on my waist I'm pulled back against a hard chest, then I feel lips on my neck. "Future Mrs. Lockwood, let's go celebrate elsewhere." Tyler breathes into my neck huskily and I feel my stomach drop. Turning my head, I stare into his brown almost black eyes, giving him a quick peck on the lips, then smile shyly. "I can't, before you get upset, I just want you to know I'm meeting Grams tonight... that's why I didn't bring my overnight bag. I'm going with her to Chicago tomorrow, well today... you know what I mean." Sheila Bennett aka Grams is the closest thing I have to family. She watched me as a child, had an awesome relationship with my mother since Shelia's daughter Abbey was my mom's best friend and then she became so much more to me when I was fifteen and my mom was taken by cancer. My dad out there somewhere in the world never bothered to come for me and I'm so thankful for it. Grams took me in and here I am two going on three years later doing better than ever thanks to that incredible woman. "Her family's bar and the apartment above it is being sold, I offered to go and help her get some old family heirlooms."

He sighs dropping his head to my shoulder but nods, "And when will you be back?" I turn around kissing him sweetly. "We'll be staying the night and coming back the next day, then we can celebrate." Shooting him a wink he grins pulling me in for a deeper kiss. Happy New Year to me, 2020 has started with surprises.

Once Tyler dropped me off at the house I now share with Grams, she instantly shot her head in my direction from her seat on the couch. She's always known when something's up with me, I simply held out my hand and she jerked her head in a nod once. Then she looked at my face and pulled me down to her wrapping me in her arms telling me that she knows my heart isn't fully in my relationship, that it's just become my normal life. That taking a day to be away from everyone and everything here in Mystic Falls, Virginia will do me some good. I need to clear my head and really think about what my heart wants, I could only nod feeling that tightness in my throat and chest again. After shooing me off to bed, I packed my overnight bag, shoes, makeup and curling iron then I fell into a restless sleep after a shower.


"Here we are." Grams announces pulling into an alleyway next to Bon's, her family's bar. Well now it's their old bar, it was once a Speakeasy back in the roaring twenties, one of my favorite eras. I'm a sucker for The Great Gatsby and was Daisy Buchanan this past Halloween even. The red brick stands out against the tanned chipped building that's next to, the sign that used to read the bar's name is a faded black and red with Script writing, the two story joint has no windows that I can see from the front or where Grams' Dodge Durango is parked at here on the side. It's beautiful though. "This place is amazing just from looking at it out here, are you sure you want to sell it off grams?" Shelia cuts the engine and leans back into her seat nodding. "It's time Caroline, it may have some good stories and weathered many storms, but it can't compete in this city any longer child." I hate that, this is a piece of history! In a time, where Mobster's ruled the streets of Chicago and alcohol was prohibited this place was a raving spot for the ones who defied the law. Where people from all different backgrounds came together to share their love of jazz music, liquor, dancing, gambling. Where women broke out of their homemaker ways and lived it up saying screw you to society. Of course, there's also the dirty deeds of the crime lords that would have their business done here. This is still freaking history! It's a huge part of Chicago's past and the city doesn't even want it as a historical piece! The insanity of that makes me crazy!

"Come on child, we've got work to do." Once we're out of the car, luggage in hand Grams opens a side door in the alley way, entering we are met with old dark wood stairs leading up to a door that's instantly on the left, the walls are a egg shell white that looks as if it's just been painted recently, looking up I realize that must be the apartment above us. Turning to my right I see a set of stained-glass double doors with a bright red 'B' in the center of each oval glass. That's obviously the bar area. I'm squealing on the inside, so many people in history have been in the place, real gangsters and well-known musicians and God what a time to have been alive back then!

We spend the day going through all the boxes that are in the apartment, it's a tiny, but cozy two-bedroom space but it's cute as can be. Grams and I look at old pictures, flyers and some bar memorabilia. She tears up at some of the pictures of her family and I fan girl out over everything that's from the Speakeasy which makes her laugh. Noticing a wedding picture, I pick up the dusty gold frame tracing the black and white photo, my fingertips leaving a trail as the dust is wiped away from the thin glass. Telling me it's her parents, I hand it over to Grams and sigh. Her hand covers mine then I'm offered her knowing smile, "I haven't seen you this colorful and cheery in a while... you needed this breather." Licking my lips, I nod then my gaze travels to the weight on my finger. "He's been a part of my life for so long now that it just felt like I had to say yes to Tyler." There I admitted that, and I know I won't be judged for the comment. "I know, that's your head talking... what does your heart say Caroline?" I open my mouth to speak, but her hand is in the air. "I have just what you need, stay here." With that she's off the couch and moving into the master bedroom, I look around the apartment from my seat on the old couch that's covered in a blue sheet, it's sans any pictures on the walls… hence all the boxes. And again, no windows.

"I got it." I look up at the tiny smirk on Shelia Bennett's face and move my curled blonde strands behind my ears. Opening the tarnished looking metal box, her hand dips into the soft blood red velvet inside pulling out a long silver chain with a matching silver heart shaped locket wrapped in what looks like red vines. It's the most simple and gorgeous piece of jewelry I've ever seen. "This has been in my family for generations, legend has it that it shows you what your heart desires. Now I don't know how true that is, but maybe just wearing it will help you figure out some things with that Tyler." I giggle, she's never been a fan of his and has never once tried to hide her distaste. She's blunt and unapologetic which I love about her even when I'm on the receiving end of her harsh truths, but I respect and appreciate it.

"Thanks Grams, really I need all the help I can get because my heart and head are in a battle and I'm stuck in the middle of it. I love Tyler, I do, but... anyway thanks." With a sly look on her face she nods and loops the necklace over my head, I pick up the heart studying it and I feel my heart skip a beat. "Well it's time for some shut eye, we've done a lot today and that drive wore me out." Placing a kiss to the top of my head Shelia then saunters into the master bedroom. After I've washed my face and brushed my teeth in the small space of the bathroom, I look out of the only window I've seen in here, with my eyes trained on the city skyline I press my forehead against the cold glass. "Sleep on it, Caroline, just sleep on it... all will be better in the morning." Once I'm in my lace boy shorts and a tight purple tank, I throw my hair up in a messy bun full of blonde curls and tuck into the full size bed with the space heater blasting heat at the bottom of the bed, clutching the locket in my hand I pray for sleep and clarity.


Rolling over I groan; the morning sun filters into the room and I tightly squeeze my eyes shut. I got the sleep I needed, sleeping better than I have in a while. Sighing my hand instantly goes to the necklace, sitting up in the bed yawning and stretching to the point of falling off the edge I tuck the necklace into my tank top. My feet hit the hardwood floor and I shiver; damn heater must've cut off in the middle of the night because it's freezing in here. With bleary eyes I remember Grams saying something yesterday about having coffee and breakfast in the bar, I rub my eyes still half asleep and blindly walk out of the apartment and down the stairs. Yawning again I pull my hair out of the bun I piled on top of my head last night feeling the strands hits my shoulders and back. With another yawn I push the double doors open. "Well Grams, that sleep was much needed just as your glorious coffee and bitching baked goods are, so fork em cause I'm hella hungry." I giggle smiling brightly while placing my hands on my hips, then my foggy eyes clear and I stand stock still. There are two mouths hanging open, two months that belong to two confused looking people that I've never met before. Well they're not the only one confused here! A girl that looks a lot like a younger version of Shelia and an extremely, mouth-watering guy with the best hair I've ever seen on a male paired with his swoon worthy jawline, full lips and mesmerizing green eyes.

"Who the hell are you? Where's Sheila?" My head cocks to the side as a brow of mine goes up. The guy leans back in his seat brows furrowed and a cocky smirk comes to his face as he points at me, "I'm sorry sweetheart, are you lost?" A smug look is now on his gorgeous face, but the way he talks is... well it's different. Guess it's a Chicago thing? "The name isn't sweetheart and no I'm not, are you two the new owners?" They both look at one another the girl and her hazel eyes flick back to me and they laugh. I force myself to contain the foot stomp I want to throw down as if I'm eight years old. "Are you okay miss? Do you need... help?" The girl asks as she steps closer to me, I eye her hair that's curled and pinned to her head, eyeing her straight olive green dress with fringes around the skirt hitting her knees then a quick glance at her brown short heeled dress shoes and cast off a frown. Shaking my head my throat clears then I look at the guy who's lounging back in a wooden chair, one arm draped across the empty one next to him... his black and white suit and dress shoes, they're odd just as her clothing is.

"Umm, help yes." I nod assertively. "I do, I need to know what's going on here and to find my guardian." I manage to say with my aggro voice, the girl shakes her head and smiles kindly at me and my hands drop from my hips. "We can help you if you let us, wont we Stefan?" Her eyes never leave mine and I hear him scoff a bit, Stefan. Interesting name and one I've only heard of once. "Were you hurt? Your... your state of undress..." My frown deepens as I look down at my tight purple tank and black lace boy shorts... oh... OH! "Oh, God no! No this, it's sleepwear. You know, a good comfy tank and some boy shorts? Perfect for bed, didn't know anyone would be here or I would've thrown on some jeans and bra." I laugh now and she looks as if she's blushing? I turn my head looking over at Stefan who looks... amused? "Are you a hooker? That a new line of clothing for you gals?" His voice has a playfulness to it, but he sounds seriously curious. However, I'm insulted.

Releasing a harsh breath, I grit my teeth and glare at the asshole, "No I'm not a hooker!" I throw my arms out wide for emphasis. "I'm a seventeen-year-old girl who drove up here from her hometown with her guardian to box up some things since she's selling her family's bar and apartment that's a hundred years old! All I want to know is where the hell Sheila Bennett is, get some damn coffee and get out of Chi-town! Okay?" I'm now breathing heavily, my blood pumping while liken my chest rising and falling and the guy coughs. "Bonnie, you need to get her out of here." I squint my eyes at him, but she grabs my arms and hauls me towards the door, however I plant my bare feet down on the black and white tiled floor. "No! No way! I'm not going anywhere, you know what? Let me find my damn phone and we can clear this up really quick, I don't who you two are but... wait your name is Bonnie?"

The girl nods, the guy growls? What? "And you said something about a Bennett and a hundred-year-old bar." She states and I nod blinking... what in the hell is going on? "Yeah, my guardian and this place, exactly as I said, hundred year old bar called Bon's." My eyes squint as I look at her, Bon's… Bonnie. Shaking my head, I continue, "The place was built in 1919 opened up as the first Speakeasy in 1920 on New Year's Day, yesterday on the first marked its hundred-year debut to the city of Chicago. All the crime bosses in here used to come down to Bon's and do their business, famous jazz singers and musicians came from getting their start here, prohibition era... Al Capone, and a few other big time Italian crime bosses ruled the city, dirty cops and so on. Flapper dresses and all that jazz? Ringing any bells now?" Her eyes are wide, she cuts them over my shoulder. The scrape of a chair can be heard then I feel a hot hand on my shoulder turning me around I'm now in the proximity of the Stefan guy. Wow, he's seriously the hottest guy I've ever seen even though he's a douche. Me and my stupid libido, focus Caroline. Tyler, engagement, Grams! Face palm mentally! A brooding frown now on Stefan's face, he stares into my eyes tilting his head a bit, "Who are you?"

I hope everyone enjoys this Stroline AU! Please read and review! :)