Chapter 1: Whiskey and a Wager
The rain had turned the bar's windows into a blurred watercolor of neon and darkness, that sickly orange glow bleeding through the glass like a wound that wouldn't heal. I wiped down the mahogany—if you could call the scarred, beer-stained slab of wood mahogany—and tried not to think about the stack of unpaid bills sitting on my kitchen table like a coiled snake.
Tuesday nights at The Rusty Nail were always slow. Slow enough that I could hear the drip of the faucet behind the bar, the low hum of the refrigerator, the way old Murray in the corner booth was breathing like he might not make it to closing time. The jukebox wheezed out something by The Replacements, all feedback and heartbreak, and I poured myself a finger of bourbon because there was no rule against drinking on the job when your boss was passed out in the office.
The bourbon burned going down. Good burn. The kind that reminded you you were alive.
I'd been tending bar at The Rusty Nail for two years now, ever since I'd realized that student loans were a trap designed by people who'd never had to choose between art supplies and groceries. The pay was shit, the customers were worse, but I got to keep my clothes on and I got to drink for free, which was more than I could say for most of the options available to a broke art student with ink-stained fingers and a chip on her shoulder the size of a boulder.
My hands moved on autopilot, wiping down glasses, restocking the well, checking the levels on the cheap vodka that tasted like regret and the cheap whiskey that tasted like regret with a hint of gasoline. I liked the rhythm of it. The predictability. The way the world narrowed to the space between the taps and the register, where nothing mattered except the next drink and the next customer and the next hour until closing.
The door opened, and the little bell above it jingled like a warning.
I didn't look up. I'd learned that lesson a long time ago—looking up meant inviting conversation, and conversation meant listening to drunk guys explain why their ex-girlfriend was crazy while they ordered another round on their credit card. But I heard the footsteps. Expensive shoes on sticky linoleum. The kind of footsteps that didn't belong in a place like this.
"You look like you're mixing that old fashioned with a grudge," a voice said, smooth as honey poured over gravel.
I looked up.
He was exactly the kind of guy I'd spent four years hating from a distance. Honey-blond hair that fell across his forehead in that effortless way that cost two hundred dollars to maintain. Green eyes that probably got him out of parking tickets and into bed with whoever he wanted. A coat that cost more than my entire wardrobe, more than my rent, more than the used kiln I'd been saving up for since sophomore year.
The coat was camel-colored. Cashmere, probably. The kind of thing you wore when you wanted people to know you had money without actually saying it.
"I'm mixing it with the same grudge I mix everything with," I said, setting the glass on the bar. "What do you want?"
He slid onto the stool like he owned it. Maybe he did. Maybe he owned the whole building and I just hadn't gotten the memo. He flashed a smile that was probably worth a thousand dollars on the open market, and I felt my jaw tighten.
"An old fashioned," he said. "And your name."
I dumped the drink I'd just made down the sink.
"That was a perfectly good old fashioned," he said.
"That was a perfectly terrible old fashioned," I corrected. "I was about to pour it out anyway. You just saved me the trouble of finding a reason."
I grabbed a fresh glass and started over. Bourbon. Sugar. Bitters. A twist of orange peel that I cut with more force than strictly necessary. The whole time, I could feel his eyes on me, tracking my movements like he was taking notes.
"You don't like me," he said.
"I don't know you."
"That's never stopped anyone before."
I slid the drink across the bar. It landed right in front of him, no spill, no wobble. I'd been doing this long enough that my aim was deadly.
"Drink your drink," I said. "Leave your money. Leave me alone."
He picked up the glass but didn't drink. Instead, he swirled the liquid around like he was examining it for imperfections. The bar's dim light caught the amber, made it glow like something precious.
"This is good," he said, sounding surprised. "Like, actually good. Not dive-bar good. Like, I-would-pay-twenty-dollars-for-this good."
"You wouldn't pay twenty dollars for anything in here."
"I might." He took a sip, and his eyebrows rose. "I definitely might."
I turned away, busying myself with the bottles behind the bar. Gin, vodka, rum, the cheap tequila that tasted like turpentine and bad decisions. My fingers found the label of the whiskey I used for old fashioneds—a mid-shelf bourbon that I'd argued with my boss about for three weeks before he'd caved—and I traced the letters without really seeing them.
"What's your name?" he asked again.
"What's it to you?"
"Curiosity."
"Curiosity killed the cat."
"And satisfaction brought it back." He leaned forward, elbows on the bar, and I caught a whiff of something that wasn't cologne. Something cleaner. Soap, maybe, or the expensive version of the same thing. "I'm Theo. Theo Vanderweil."
I knew the name. Everyone knew the name. Vanderweil Hall was the ugliest building on campus, all glass and steel and the kind of architectural arrogance that came from a family with a building named after them. The Vanderweils had donated so much money to the university that they'd probably gotten their own parking spaces. Probably their own zip code.
"Maya," I said, before I could stop myself. "And before you ask, no. I don't want to hear about your thesis. I don't want to hear about how you're slumming it for research. I don't want to hear about how fascinating you find the working class or how your family doesn't understand you or how you're just like me, really, underneath all the privilege. I've heard it before."
He blinked. For a second, he actually looked thrown.
"That's..." He paused. "That's not what I was going to say."
"Sure it wasn't."
"I was going to say that this is the best old fashioned I've had in years, and I was wondering if you'd teach me how to make it."
I snorted. "Why would you need to know how to make it? You can just pay someone to make it for you."
"That's fair." He took another sip, slower this time. "But I'm trying to learn things I can't buy."
"Like what?"
"Like how to talk to people who don't want anything from me."
I grabbed a rag and started wiping down the bar, even though it was already clean. The motion gave me something to do with my hands, something to focus on besides the way his green eyes were watching me like I was a puzzle he was trying to solve.
"Everyone wants something from you," I said. "You just don't like the price tag when it's not cash."
"That's cynical."
"I'm a bartender. Cynical is in the job description."
He laughed. It was a real laugh, not the polite one I'd expected, and it caught me off guard. I glanced at him before I could help myself, and he was smiling at me like I'd said something genuinely funny instead of just bitter.
"Okay," he said. "Okay, I deserved that."
"You did."
"I did." He set his glass down and reached into his coat. I braced myself for the credit card, the black Amex, the thing that would prove my point about who he was and what he wanted. Instead, he pulled out a crisp hundred-dollar bill and laid it on the bar.
"What's this?" I asked.
"A proposition."
"I'm not a prostitute."
"It's not that kind of proposition." He held up his hands, palms out. "I need a fake girlfriend."
I stared at him.
"I'm serious," he said. "My sister's getting married next month. Big wedding. Whole family's going to be there. And my mother has been trying to set me up with the daughter of some business partner for the last six months, and if I show up alone, I'm going to spend the entire weekend being paraded around like a prize stallion at auction."
"That's terrible," I said. "Truly. My heart breaks."
"I'll pay you a thousand dollars."
I picked up the hundred and held it out to him. "I'm not interested."
"You didn't even let me finish."
"There's nothing to finish. I'm not playing pretend with you so you can avoid your mommy's matchmaking. I've got my own problems."
He didn't take the money. Instead, he just looked at me, and there was something in his expression that I couldn't quite read. Not desperation. Not pleading. Something closer to curiosity, like I was a puzzle piece that fit somewhere he hadn't expected.
"One weekend," he said. "That's it. You show up, you smile, you hold my hand, you pretend to be enchanted by my charm and good looks, and then you leave. A thousand dollars for two days of work. That's five hundred a day. Way more than you're making here."
"I make plenty."
"You make twelve dollars an hour plus tips. I've been watching you for the last forty-five minutes. You've served exactly two customers, and one of them was Old Murray over there, who's been nursing the same beer since I walked in."
I felt my face heat. Not embarrassment, exactly. Something closer to anger.
"You've been watching me?"
"Hard not to." He shrugged, and the movement made his coat shift, exposing the soft wool of his sweater underneath. Gray, probably cashmere. Definitely expensive. "You're the most interesting person in here."
"That's not saying much."
"It's saying something."
I put the hundred back on the bar and pushed it toward him. It sat there between us, a green rectangle of temptation, and I thought about the stack of bills on my kitchen table and the kiln I couldn't afford and the fact that my landlord had been leaving increasingly pointed voicemails about the rent.
"No," I said.
"Why not?"
"Because I don't do things like this."
"Things like what?"
"Pretend." I met his eyes, and I didn't look away. "I don't pretend to be something I'm not. I don't playact for money. I don't let people like you buy me."
The words hung in the air between us. I expected him to get defensive, to pull out the wounded pride that rich guys seemed to keep in their back pockets like a spare wallet. Instead, he just nodded slowly, like I'd said something that made sense to him.
"Okay," he said.
"Okay?"
"Okay." He picked up the hundred and put it back in his coat. "You're right. I shouldn't have asked."
I blinked. "That's it?"
"What did you expect?"
"I don't know." I grabbed my rag again, started wiping down the bar for the third time in ten minutes. "I expected you to argue. To tell me I was being unreasonable. To explain why a thousand dollars is a lot of money for someone like me."
"Someone like you?"
"Someone like me."
He was quiet for a moment. The jukebox had shifted to something slower, something with more soul, and I could hear the rain picking up outside. Old Murray coughed in his booth. The refrigerator hummed.
"You're right," he said. "A thousand dollars is a lot of money for someone like you. And that's exactly why I shouldn't have asked. I wasn't thinking about you. I was thinking about what I needed. And that's..." He trailed off, shaking his head. "That's the whole problem, isn't it?"
"I don't know what your problem is."
"Neither do I." He finished his drink and set the glass down, neat and precise. "But this is the first honest conversation I've had in weeks, and I'd like to have another one. Not for a thousand dollars. Not for a fake girlfriend. Just... another conversation."
I should have said no. I should have told him to get out of my bar and go back to whatever country club he'd crawled out of. I should have protected myself, protected the carefully constructed walls I'd spent years building.
Instead, I grabbed two glasses and poured two fingers of the good bourbon.
"Another conversation," I said, sliding one across the bar. "But you're paying for the drinks."
His smile was slow and warm and dangerous in a way I didn't want to examine too closely.
"I'll drink to that," he said.
We talked until closing time.
I didn't mean to. I meant to pour him one drink, suffer through ten minutes of small talk, and then kick him out with the rest of the stragglers. But somewhere between the second round and the third, the conversation shifted into something I wasn't expecting.
He told me about his sister, who was marrying a guy named Marcus who'd once tried to sail across the Atlantic and had to be rescued by the Coast Guard three days in. He told me about his mother, who had opinions about everything and expressed them frequently and loudly. He told me about his father, who'd made a fortune in real estate and had never quite forgiven his son for choosing economics over business.
I told him about sculpture. About the way clay felt under my fingers, the way you could shape it into anything if you knew what you were doing. About the kiln I'd been saving up for, the studio I dreamed of opening, the quiet that came when I was working with my hands.
"That's what I want," he said, somewhere around midnight. "That thing you have. That thing where you know what you want."
I laughed. "I don't know what I want. I just know I'd rather be broke doing something I love than rich doing something I hate."
"That's the same thing."
"No, it's not." I topped off his glass, even though I should have cut him off two drinks ago. "Knowing what you don't want is easy. Knowing what you do want—that's the hard part."
He was quiet for a moment, watching me. The bar light was dim, flickering occasionally when the old wiring gave out, and in the shadows his face looked softer. Less like a trust-fund prince and more like a guy who was just as lost as the rest of us.
"Can I ask you something?" he said.
"You just did."
"Something else."
"Knock yourself out."
He leaned forward, elbows on the bar, and I caught that clean scent again. Soap and something else. Something that made me want to lean closer, even though I knew better.
"Why did you say no?" he asked. "I mean, really. It's a thousand dollars for two days. You could buy that kiln. You could pay your rent. You could... I don't know. Whatever you wanted."
I considered the question. The bourbon made my thoughts loose and warm and honest, and I couldn't decide if that was a good thing or not.
"Because you don't actually want a fake girlfriend," I said. "You want someone to make you feel less alone at your sister's wedding. And that's not something you can pay for."
He didn't say anything. But something in his expression shifted, a wall coming down or a door opening, I couldn't tell which.
"You're probably right," he said.
"Probably?"
"Definitely." He finished his drink and stood up, grabbing his coat from the back of the stool. For a second, he looked like he was going to say something else. Then he just smiled, small and crooked and real. "Thanks for the drinks, Maya."
"That'll be twelve dollars."
He laughed and pulled out his wallet. This time, he paid with a card—no hundred-dollar bills, no grand gestures—and left a tip that was generous but not insulting.
"I'll see you around," he said.
"Probably not."
"Probably yes."
The door opened, letting in a gust of wet air and the smell of rain. Then it closed, and he was gone, and I was alone with the quiet and the flickering lights and the ghost of whatever had just happened.
I poured myself another drink and didn't think about his green eyes or the way he'd said my name or the fact that I'd told him things I didn't usually tell anyone.
At last call, I locked up and walked home barefoot, my heels dangling from my fingers. The rain had stopped, leaving the sidewalks slick and shining under the streetlamps. I liked the feel of cold concrete against my soles. Liked the way it grounded me, reminded me that I was real and solid and here.
I thought about Theo Vanderweil and his thousand-dollar coat and his thousand-dollar smile and the way he'd looked at me like I was something worth knowing.
I thought about the way he'd accepted my no and didn't try to change it.
I thought about the way his green eyes lingered on me when I said it, like he was memorizing the shape of my refusal.
I told myself it didn't mean anything.
I told myself I'd never see him again.
But somewhere deep in my chest, in the place where I kept my dreams of galleries and kilns and a life that didn't require scrubbing beer stains out of my clothes, I knew I was lying.
The real danger wasn't the lie he'd asked me to tell.
It was the way I wanted to hear him ask again.