She smiles when she sees you and lets out a whistle. “Look at you, babe!” You roll your eyes back at her playfully. “Yeah, yeah far removed from a school-approved outfit,” you say.

She pats your shoulder. “You look great, hon. Okay! You had your training session two days ago right? Do you have any questions?”

You lace your hands together in front of you surveying the bar. The Goldfinch is one of Chicago’s prime evening entertainment locations, quickly gaining popularity for its ability to strike a balance between the smooth luxury of a cigar club and the breeziness of a patio bar. Bottle service without the tacky sparklers or signage; just an employee there to chat with, keep the drinks flowing, and celebrate events with class. People came by for all sorts of things: birthday parties, work promotions, bachelorettes, and just casual time-pass.

You drew in a breath. “So, I’m a bottle girl… but not a bottle girl? I guess I just don’t know how this whole thing works.”

Becca chuckles at that as she grabs a rack of whiskey glasses and starts polishing them one at a time. “Think of it like, a full-time room reader and sales lady. Your whole goal is to get people to order just one more round of drinks or food that they normally wouldn’t have. If you see a birthday party, send over a glass of champagne for the birthday girl only. The rest of the guests will order a bottle. If you have a couple, send over a free dessert and they’ll order an extra drink. If someone’s drinking on their own, go see if they want someone to chat with. Flirt a little, get ‘em interested, and they might turn one drink after work into dinner.”

You nodded slowly. “But I’m not supposed to go home with anyone,” you say it as a statement. Becca’s eyes widen as she finishes the last whiskey glass and sets it down.

“Absolutely not, that’s actually like, the one no-no of working here. If a guy asks you to leave with him, you have to make it abundantly clear that you’re going out with him as yourself, after your shift is over, and you can’t accept any tips from him for the night. And absolutely no being seen outside of here with a man in your uniform. Boss is super particular; he doesn’t want people thinking this is a… like, sex house, or whatever.”

You nodded again, slowly. “Okay. I think i got it. And Becs?” She cocks her head, green eyes sparkling. “Thanks for getting me this job. Seriously.”

She smiles, pulling you in for a hug. “You’re gonna do great, hon.”

-

The first hour and a half of your shift go by fairly smoothly. You convince a bachelorette party to splurge on a bottle of dom instead of the house champagne, gushing over the bride-to-be’s ring and complimenting her friends’ outfits. You get a group of middle aged men to order black label after fawning over their company “going public,” whatever that means.

You settle into a rhythm, collecting tips and feeling slightly less out of your depth. You get a small break in between patrons and sit at the bar where Becca makes you a Moscow Mule. You sigh in relief when you take a sip, sharp and tangy notes of ginger and lime hitting your tongue. “Got another for ya,” Becca says, nodding towards one of the high tops in the corner, overlooking the busy city streets below. You follow her gaze to find a man, maybe a few years older than you, sitting by himself in a brown suit. He’s nursing a miller lite, surveying the city. You can tell he’s around the same age as you, maybe a little older as you slowly make your way towards him, taking in his perfectly imperfect brown hair, the small sun spots dotting the exposed skin on his neck.

“Hi,” you say, softly. He turns and looks at you, eyebrows raised slightly and a smile already crossing his features.

“Hello,” he says, expectant.

You sigh, gesturing towards his drink. “I just, uh, noticed you’re drinking maybe the safest option on our menu, and wanted to see if you’d be interested in trying a Chicago handshake? On the house.”

He breaks out into a full grin, eyes still reserved. His shoulders shrug up a little in surrender. “I’d say yes but I wouldn’t know what I was getting myself into.”

“Oh! Sorry, I shouldn’t have assumed you were local. It’s a shot of Malort and a tall can of Old Style. I’d do the shot with you, nobody should try malort for the first time on their own,” you giggle, which draws a small laugh out of him, too. He lifts his hand slightly.

“You know what, sure, when in Rome, right?”

You throw a wink his way as you write “Chi shake - OTH” in pink glitter on your notepad and turn away to the bar to get him his order.

You walk back with it a few moments later and set the shot glasses and beer in front of him, asking if it’s okay for you to take the empty chair across from him, which he offers up in a heartbeat.

You sit and cheers him, taking the shot and feeling the familiar allspice burn down your throat. You chase it with a sip of your mule, which you’re all too grateful to Becca for at the moment.

You watch as Steve tries his best to cover up how unpleasant he finds the liquor, his large gulps of old style giving him away and making you let out a quiet laugh. “I-I thought you were supposed to get me to order more stuff from the menu,” he says between small coughs and laughter.

You raise your hand in mock surrender. “You got me there. It’s my first night, actually.”

“Ah,” he says. “Well I’m probably a good first customer. I’m here for a work conference—advertising stuff. I live in Indianapolis.”

You lean in a little. “Really? Do they have you on the greatest hits tour this weekend? the bean, the riverwalk, all of that?”

Steve chuckles. “You’ve lived here a while haven’t you?”

You nod. “Since college. Moving here uh… moving here kinda saved my life.” You’re not sure why you’re offering up such a deep part of you to this stranger a few minutes after meeting him. You decide to chalk it up to the alcohol and maybe the way his eyes feel scarily like home. You shake your head microscopically. Definitely the alcohol. For a horrible moment you felt like you’ve said too much.

But instead of recoiling at the vulnerability, Steve just smiles again, corners of his eyes crinkling. “You sound like all my friends. We’re all from a little town in Indiana. They all moved to the east coast after, uh, after high school. I-I don’t know, I guess I just found it harder to leave. Indy’s as far as my head let me go, I guess.” He sips his beer.

You reach over and place a gentle hand on his forearm. The sun is almost fully set outside of the window, golden hues of streetlights mingling with the red of car brakes. He looks down at the touch, and leans into it ever so slightly. “I get that,” your voice is quiet. “Honestly… as much as I’ve loved living here, there’s not much keeping me anymore. My uh… ex dumped me like two months ago, and then I lost my job almost immediately after. So, I’m uh, staying with Becs,” you nod towards her at the bar, “until I can get back on my feet.”

Steve nods, “Yeah, I’ve got what you’d call an extremely sorrowful dating history, too.”

You smirk at him. “What; no wife or girlfriend waiting for you in Indy?” You’re not really sure where the boldness is coming from, but Steve’s arm is warm under your arm and he’s looking at you like you’re the only thing in the world, and nobody’s looked at you like that in a long time.

He mirrors your expression. “No, just a lofty apartment that’s too quiet at night. I don’t know, I’ve tried so hard to find the one, you know? But none of it’s worked out. When I was 20 I thought I’d be married and on kid number four by now,” he shrugs, finishing off his beer.

You tighten your grip on his arm a bit at that, nodding sympathetically. “I hear you. I thought I would be getting married this year, too,” your voice drops to a whisper and you have to look away from his intense gaze so you don’t cry.

Steve shifts under you and you go to move your hand off of his arm but he covers it with his much larger one before you can; palm warm against your skin. “Can I ask you a kind of crazy question?”

You tilt your head towards him.

“Do you.. would you wanna get out of here? Go for a drive? You can show me the best sights Chicago has to see by nighttime,” the look on Steve’s face is one of pure hope.

You nod. “Yeah, but… there’s some conditions first.”

Steve agrees to wait until the end of your shift, nursing a beer for the remaining two hours until you finally emerge from behind the bar, dressed in your normal clothes; a pair of denim shorts and a tank top, backpack thrown over a shoulder. He holds his arm out for you to take, tipping his head a bit dramatically as you giggle and loop your hand through the crook of his elbow. You catch Becs’ eye as you’re leaving and expect some type of judgement from her, but she just smirks and winks and mouths be safe like this was her plan all along.

Steve leads you to his car, a maroon BMW in impeccable shape for its year make. He ducks his head when you compliment it and opens the door for you before rounding the hood to the drivers’ side. “So, any specific requests for what you wanna see?” You ask, looking over at him in the dark interior. You feel shy; the intimacy of the car and how it smells like Steve hitting you all at once.

“Where can I get a good view of the skyline?” He asks. You smile. “I know just the place.”

-

On the drive, Steve tells you about his closest friends from high school. “Wait, let me get this straight,” you say, eyes bright and a playful smile on your face. “Your closest friends are your ex-girlfriend, the girl you had a crush on after her that turned out to not swing your way, and the guy who beat you up in an alley, who’s dating your ex girlfriend?”

“I wouldn’t say he beat me up, exactly,” Steve argues.

You laugh, high pitched. “That’s what you choose to focus on?”

Steve raises his hands in mock surrender. “Okay, you got me. It got… complicated for a bit there but, we’ve just ah- been through a lot together.” His voice softens on that last sentence and your heart swells for him.

You nod. “I get it, Becca’s my best friend but I’d be lying if I said we didn’t have our moments, too.”

He throws you a look of appreciation, for getting it, before focusing back on the road.

“Okay, turn right over here, and then park anywhere in this lot,” you say. Steve follows your directions, expertly parallel parking which you compliment. He blushes again, it reaches the tips of his ears and makes heat bloom low in your belly at the effect you have on him.

You lead him a ways away from the entrance and down the concrete steps, by the lake. You gesture out to the entire Chicago skyline that’s glimmering back at the two of you. “Ta daaa,” you hum a little, which makes him chuckle and put an arm around you, squeezing gently. You still for a brief moment and he pulls away, shoving his hands into his pockets as the two of you walk a little closer to the concrete edge. “Sorry, sorry, I shouldn’t have—“

“No!” You interrupted, grimacing at your voice being louder than you wanted. “I mean, I didn’t take it as inappropriate or anything just um, I guess I’m a little out of practice, being down on my luck and all,” you shrugged, trying to play it off. Steve didn’t laugh with you or make a joke. He just looked at you with soft eyes that you could make out in the dim light of the trail, leaned closer and wrapped his arm back around you, allowing you to sink into his touch as you both looked out to the skyline.

“Hmm, which one’s your favorite?” He asked. You could feel the vibration of his voice through your body.

“My favorite building?”

“Mhm”

“Oh, it’s the one from adventures in babysitting,” you chuckled, pointing to it. “The diamond shaped one. It just draws my eye every time I look at the skyline.”

Steve hums next to you. “I love that movie,” he murmurs.

You turn slightly towards him in his hold. “Yeah?”

He nods, looking at the skyline for a moment before looking back at you. “So, if you had to say, completely objectively. Would this be a good spot to kiss a girl you met over drinks at some swanky bar a few hours ago?” His voice is lilting with the premise of a joke; something he can use as a cop out if he needs to, but his eyes give him away.

Normally, you’d say something snappy and end this right then and there, taking a taxi back to Becca’s and tucking in for the night with a pint of cookies and cream. Normally, you wouldn’t have stayed at Steve’s table that long or done a shot with him. But you’d been doing things normally for years and that had gotten you dumped, single, and out of a job you loved all before you turned 26.

Feeling a rush of confidence, you turn fully towards him, backing him to the edge of the concrete step behind him, wrapping your arms around his neck. “Yeah, I’d say it’s perfect, Steve,” you’re sure your smile is a little too eager, but you can’t find it in yourself to care because every one of your senses is filled with Steve as he presses himself closer and captures your lips with his. He tastes like beer and mint and something unique to him entirely. You whimper when he swipes his tongue across your bottom lip, which makes him smirk into the kiss. You open for him, letting his tongue meet yours and explore your mouth, drawing out more sweet sounds from you as you move one of your hands from the back of his neck to the inside of his jacket, pulling him impossibly closer. His fingers tighten their grip on your waist to reciprocate, kissing you again and again before he finally pulls away.

You both let out incredulous laughs as you rest your foreheads together, lost in the moment and each other.

“You know, maybe I was wrong,” you whisper.

Steve hums in questioning.

“Maybe my luck’s starting to change.

You feel him smile as he presses another kiss to your mouth, leaving you chasing his lips for more as he pulls away.

“Can I ask you another crazy question?” He says, mirroring his question from earlier in the evening.

You nod, looking into his eyes.

“Will you stay with me this week? I have a suite that’s too big and lonely for me to survive by myself.”

You scoff a little. “Wow, use that on every girl, do you?”

His brows furrow. “What? N-no! I swear. This isn’t some ploy to sleep with you. If I wanted that I would’ve just asked but—look, we’re both a little sad and life’s not being so kind, and we clearly like each other enough to make out with each other and reveal our reasons for heartbreak so… I figured we could do something a little crazy.”

You mull it over in your head before a smirk creeps up your lips. “I think you’re on to something, Harrington. But there’s rules,” you say, quoting your earlier exchange playfully back to him as you peel yourself away from him and grab his hand, leading the way back to his car.