AN: This is the first time that it's more than one scene so here it goes:

Chicago I: Starts right after Elena calls Tyler after finishing her Katherine hair.

Chicago II: Elena's perspective of going to see Dean, right after Dean wakes up and realizes she's gone.

Chicago III: Ryan and Elena in the club, between Ryan calling Elena fearless and Elena telling him why she always outsmarts him.

Addendum: Outtakes

Excerpt from Ch. 18

Chicago I, II, & III

Illinois: June 2018

Chicago I

"You want Ryan to help you pretend to be Katherine?" Tyler asks for umpteenth time.

Elena rolls her eyes, watching herself in the mirror. "Yes, Tyler, I can't exactly go around compelling people like she would, and I'm definitely not going to bite anyone."

Staring at Katherine's reflection in her place she thinks of her dream back in Toledo, perfect antebellum curls and cherry lips smirking around fangs. This time Elena is the girl, not the reflection, but the effect is the same. All Elena has to do is curl her hair and put on a little smoky eye and suddenly she's a completely different person.

"You sure about that? 'Cause from what I remember from the locker room, you've got some teeth on you."

They both flinch.

Elena watches her face crumble in the mirror, and it's unquestionably her. Being reminded of someone could never make Katherine crumble like that.

Tyler is quiet on the other end of the line and Elena knows she has to salvage this.

"I can't imagine Matt Donovan telling any locker room about my teeth," she says lightly, watching herself barely manage to repress flinching when she says his name.

Tyler takes a deep breath, tries to match her tone.

"Of course he didn't. But it's not like he could hide the bitemarks."

Elena watches Katherine's face, praying it won't crumble into her own.

"This is surreal," she says, Katherine's face firmly in place.

Tyler laughs because it is, they're sitting here ribbing each other about Elena's past sex life with a guy whose death utterly destroyed both of them. Ordinarily neither of them can even say his name, but here they are, caught up in their memories of being teenagers. First loves, first times, sexual awakening and all the dirty, silly, and embarrassing parts of growing up. In reality it's only been a few years, but they both feel lifetimes away from those wild, curious teenagers.

"I could compel people for you?" Tyler offers finally.

Elena watches Katherine's face, the way her eyes roll, the decisive shake of her head and the derisive smirk. It's all perfectly in character, perfectly Katherine.

"You aren't friends with Katherine," Elena reminds him.

"You are," Tyler points out fruitlessly.

"You wouldn't help Katherine even if I asked you to," she replies.

Tyler sighs because he knows she's right. Elena is the only one who's on good terms with her doppelganger, the rest of them wouldn't give her a blood bag if she was desiccating.

"And there's no one else? It has to be Ryan?" he asks, reluctant to let the other hybrid out of his sight just yet.

"Katherine would think it was hilarious," Elena says more grimly than she means to.

"Yeah, she would." Tyler can't help but agree. Anything that plays into the their similarities is something that brings Katherine great amusement. It's more unbelievable that Katherine hasn't found Ryan already.

"The thing is, Elena," Tyler begins somewhat queasily. "Ryan is…volatile. He doesn't have great control, and he's definitely obsessed with you. This situation could get out of control very easily."

Elena chews on her lower lip. "It doesn't matter, it has to be him. Katherine wouldn't hang out with any of the other vampires or hybrids I know. Ryan is the best bet I can make right now."

She leans forward, checking her lipstick in the mirror. It's still perfectly, sinfully red, not at all smeared, her teeth sparkling white, it's well-worth the money she spent on it.

Tyler sighs. "All right, I guess Ryan's going to Chicago."

"Thank you, Ty, I owe you one, seriously," Elena says, relief flooding through her.

"I really don't think you do," Tyler replies seriously.

After they hang up, Elena looks at Katherine's reflection again. The memory of Matt had almost broken her open. He was Elena's friend, not Katherine. Katherine liked his blue eyes, that's it. Nothing about him or his death would break her heart.

So, Elena thinks about Matt until her eyes maintain that narrowed, calculated gaze Katherine is so well-known for. It's like pulling her own stitches out of an infected wound, but survival is the most important thing right now.

So, she practices, thinking of all the people she loves, specifically the ones she lost. Her mother, her father, Uncle John, Aunt Jenna, Matt – and Katherine tosses her curls impatiently, fixes her mascara.

Next, she thinks about Caroline and Bonnie, Jeremy and Sam, John Winchester. All still alive, but people Elena Gilbert would do anything for. Katherine fiddles her necklace petulantly.

Somehow Elena maintains her façade through all of it. Happy memories, brutal memories. Holding Jeremy as he woke up after Damon killed him. Her mom brushing her hair. Her dad teaching her how to ride a bike. Sharing ice cream with Aunt Jenna. Uncle John's last letter to her. Sleepovers and cheer camp with Caroline and Bonnie.

Even newer memories, Tyler helping her find that creepy farm to rescue the boys. Sam drunkenly declaring his love to his birthday cake. John Winchester holding her tight against his chest, heart thundering as he confronts the oldest vampires in the world for her. She is impervious to them all. Katherine's face stays firmly in place in her reflection. She looks bored, amused, annoyed, never distraught or happy or fond, never Elena.

Finally, with the lightest of breaths, she lets herself think of Dean. It's like a barrier has broken, it floods across her face with breathtaking speed, changing everything about her until she is raw and nakedly herself.

"Fuck," she whispers. She'll have to work on that.


Chicago II

There was a moment, in the alleyway, the weight of both men, the bartender and Ryan, nearly suffocating even as Ryan held most of their weight off her. The smell of blood thick in the air, the feeling of it seeping down her neck, staining her red dress redder, and she opened her eyes because she couldn't escape the idea that they weren't alone in that alleyway, the three of them.

There had been no one in sight, and then Ryan was pulling the bartender off her and compelling him and she handed him the paper towels that she stuffed into her clutch in the bathroom to staunch the bleeding. Ryan had looked at her with raw wanting with the smell of fresh blood on her skin but all she wanted was to be away from him.

She told him to make sure the bartender got home safely and before she knew it, she was picking the lock of the door of some motel room, the Impala in the parking spot behind her.

She didn't plan it, she just couldn't escape the feeling that someone was there in that alleyway, watching her play at being a monster, and she hated herself – hated being Katherine– so fiercely that the only place she knew to go was here. The only person she wanted to see was Dean.

It was a bad idea for so many reasons, starting with being Katherine and ending with it too. She wasn't supposed to be seeking out people Katherine wouldn't hang out with, and she'd said a horrible thing to Dean that she didn't even mean because she'd still been thinking like Katherine, not herself.

He'd forgiven her so quickly; it had been all too easy to fall asleep in his arms. It's much harder, extracting herself from his embrace, slipping back into Katherine's bloodstained dress and towering heels, hiding her scars beneath nylon, leaving his shirt folded at the end of the bed.

She barely remembers the decision to put it on in the first place, only that Katherine's dress and face had been unbearable to her in the bathroom mirror, and she had needed to see herself, needed to smell something else on her skin other than blood and expensive perfume.

She allows herself the indulgence of a kiss to his cheek, inhaling the scent of his skin that still clings to her from wearing his shirt and sleeping in his arms all night, wondering if it's always been this hard to leave him or maybe it's worse now that she has to leave herself too.

She finds her way back to Katherine's foreclosed mansion in the gray early morning light. She's not in the least bit surprised to find the club girl from last night on the couch, a bloodstain spreading from her throat. Thankfully, she's only sleeping, she discovers when she checks for a pulse.

Ryan is passed out naked in the king-sized bed in the master bedroom she claimed for herself. It's clearly an attempt to force her either into bed with him or to retreat to another bedroom and concede control.

She snorts. "Cute."

In the bathroom she finds a silver ice bucket – engraved with a wedding date dated only 11 months prior – perched next to the jacuzzi tub. She fills it with water and adds a little something she filched from the Impala's trunk on her way out.

She marches back into the bedroom, using the momentum from her movement to toss the contents of the silver ice bucket directly onto Ryan's sleeping figure. He wakes up screaming and cursing, smoke rising from his skin.

"What the fuck?"

Elena smiles at him, it's a lot easier to look at him when he doesn't look the least bit like Dean, lacking skin and all that.

"Vervaine," she says helpfully. "Now get the fuck out of my bed."

"Seriously? I'm helping you and this is how you treat me?" He glares at her as he climbs out of the bed unsteadily, making for the bathroom. "You've been nothing but mean to me since I got here. I'm sick of it."

"And you've been nothing but creepy. I asked you to compel people for me, leave a few bitemarks, not invade my privacy and make me uncomfortable," she retorts shortly.

He whirls around, glaring at her. "Well maybe that's the price for my help. Your bed and your-"

She cuts off what is sure to be an extraordinarily crude comment.

"No, there is no price. You're helping me because Tyler asked you to. Tyler who is helping you break your sire bond to Klaus." She smiles. "Klaus, who would hand me your still-beating heart if I told him I wanted it."

He flinches. "Everyone says you're the nice one."

She moves closer. "I'm not Elena right now," she reminds him.

Wariness creeps into his expression, but it's far too late.

She slams him into the bathroom door, his still raw skin making brutal contact. He lunges for her with supernatural speed, only to impale himself on an elaborately carved wooden hair pick she found in the bathroom, clutched in her fist like a dagger. It's just long enough that if he moves any closer to her, he will drive it into his own heart, rendering him unconscious and completely vulnerable to her.

She presses her forearm against his throat, holding the hair pin inside of him and angled towards his heart.

"Stay. Still," she enunciates. "And listen carefully."

He stays perfectly still, eyes wide with fear.

"I don't know if that girl asked to come home with you, but she will go home in perfect condition, do you understand me?"

He nods, disbelief clear in his eyes.

She bares her teeth, entirely human, but nonetheless threatening. "I am a hunter. I protect innocent girls like her from monsters like you. As long as we are here you are not going to bite anyone that I don't tell you to, got it?"

He nods again, jaw clenched.

She twists the hair pin still inside of him, watching him flinch in pain. Satisfied that she's made her point, she releases him, pulling the hair pin out.

She points it at the door. "Get the hell out of my room."

He goes, leaving a bloodstain in the shape of his shoulders on the bathroom door.

When he's gone, she peels herself out of the bloody dress and scratchy stockings and takes a shower hot enough to burn off three layers of skin.


Chicago III

"That's none of your business, and frankly this is the wrong place to bring it up. Do you not remember what we're supposed to be doing right now?"

He continues like she hasn't spoken.

"I really don't get it, you can have any guy you want; Klaus is practically panting after you, but you just keep everyone at arm's length and then look at him like…like he's the only thing that makes sense to you." He shakes his head. "I really don't get you."

"Reminding me that you stalked me isn't endearing you to me at all; and how I look at him is none of your business," she says flatly. "And he's not boring. Or strait-laced," she adds before she can stop herself. "Any more than I'm fearless or crazy."

"I'm a hybrid, I should be able to squish you like a bug, but you keep surprising me. You keep out-maneuvering me." He shakes his head. "Completely wasted on him."

She cocks her head to the side. "What you don't realize is that you're out of your depth."

He looks offended, but she plows on.

"You think I'll just hop into bed with you because you bear a passing resemblance to someone I care about, but you don't realize that that's not how it works."

The waitress comes then, bringing their drinks. Elena takes a delicate sip of her wine and is surprised to find herself continuing. It's like he's opened a sieve inside of her and she can't quite close it up again.

"You don't see that when Klaus is looking at me, he's comparing me to every other pretty Petrova who's passed through his bed. Maybe he likes what he sees, but he liked what he saw in them too. We're all the same to him. I just happen to be the one that gave him what he wants." She looks up at him, bitterness evident in her gaze. "I just happen to be the one willing to play by his rules."

She leans in, intense in a way Ryan is not prepared for.

"I don't want a lookalike," she says bluntly.

She cocks her head to the side, sweetly disarming, and attacks from another angle. "You wanna play with the big kids, but you don't even know the game. You don't understand that you're not a player, you're a toy."

She swirls the wine in her glass, deceptively casual.

"This is where you belong, in clubs, stalking party girls who will wake up the next day – or hell, maybe a few days if you're having a good enough time – with a sore throat and a gap in their memory that they'll blame on the alcohol. Give it a few years, some low-grade hunter will cut off your head in some back alley and go home with your mark after celebrating a job well done. The hunter will move on to the next job and the girl will never know that he – or she – saved her life. That's the job."

She shakes her head. "I am not wasted on anyone, Ryan. In another version of this story, you're just the monster of the week we finish off before going out for pizza and beer." She gives an exaggerated sigh of exasperation. "But you just had to play with the big kids."

He glares at her. "Klaus picked me."

She raises an eyebrow. "That's not how he tells it." She leans back, making herself comfortable against the plush leather. "He told me you begged him for it."

The corner of her jewel-colored mouth quirks in a way that twists his insides.

"Yeah, but he wouldn't have done it if he didn't think I was worthy-"

She cuts him off. "Don't flatter yourself. You look like Dean Winchester," she says this flatly, like it isn't something that makes her sick to her stomach. "That's the only special thing about you." She cocks her head to the side, sympathetic, almost. "You're a toy, a pawn. You exist to piss me off, to make John uncomfortable, to give Klaus some kind of an edge over us."

She leans forward onto her forearms, hands clasped, looking utterly fatal.

"You couldn't have survived Klaus' gift if it wasn't for me."

Ryan stares at her – at the girl whose blood gave him new life. "I know that."

"Do you?" She challenges. "Act like it."

He looks sufficiently cowed for a moment, but she isn't done.

"I was a pawn once too – albeit a much more valuable one than you could ever be – but I did something about it. I didn't squander every opportunity for leverage that I had."

He glares again. "I haven't squandered anything."

She cocks her head to the side. "Really? You think Tyler – the only person willing to help you – is gonna be thrilled to hear about how you've acted in the past two days? You think Klaus is just gonna be cool with it if he ever finds out that you stalked me?"

She takes a drink again, watching as the color drains from his face as the ramifications of his actions start to sink in.

AN: I recognize that I didn't need 1k words of Elena telling Ryan he sucks but...I really enjoyed writing it. Also Klaus telling Elena that she doesn't compare to any of the other doppelgangers makes more sense when you consider that he overheard her telling Ryan that that's all he sees when he looks at her.

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xoxo

-Pixie