Chuck Bass X Reader: Late Night Conversations
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Masterlist
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Summary: Reader works in a shitty bar that Chuck ends up buying. Slow burn, slight romance, and nice! Chuck.
Warnings: mentions of multiple addictions, descriptions of shitty lives, alcohol consumption.
Word count: I'll get back to you...
A/n: Chuck has a special place in my heart. Yes, him and Blair will always be the perfect couple, but... what if they weren't? Also, aged up characters for this fic, everyone is 23+.
~
"What can I get you?" You asked as you turned to the new customer, a small smile plastered onto your face.
"Rum and coke please," the man answered, not looking up from his phone.
God you hated the clientele here, but fuck did they tip well when you wore a short skirt.
"Single or double?" You kept the same fake expression, though you knew he wasn't even looking at you.
"Single."
"You got it!" You said cheerfully, mustering all the excitement you could. You turned around and grabbed a single glass, adding ice before counting out a shot of house rum. You filled the glass with pepsi from the pop gun and tossed in a straw before handing it to the guest.
"Are you starting a tab or paying for that now?" You asked, leaning forward on the bar slightly to hear his response better. He was pretty quiet.
"Now, I have cash." The man pulled out a ten, grabbed his drink and sauntered off towards a group of men occupying the corner table.
"Thanks!" You called as he left. You rung in the drink and cashed it off, taking the change as your tip. You glanced around, checking beer and highball glasses to see if anyone needed a refill. You then looked for empty plates, spotting one and heading to it.
"Are we all finished with this?" You asked politely as you approached. They nodded yes and you took it out of the way, heading back to the kitchen. You made a left to the dishpit and smiled at TJ, your regular dishwasher.
"How's it going out there, (Y/n)?" He always made small talk when he had a second.
"Good! Got a few tables and a few sitting at the bar, can't complain," you replied, spinning on your heels to head back out. Your boots were heavy against the floor, your footsteps letting everyone know you were returning.
TJ was the only one left in the building other than you, and he would be finishing up soon, leading to the worst part of your night; working and closing the bar alone.
Only another forty-five minutes and you could do last call, it was getting late.
A man stood at the entrance to your bar, VLT ticket in hand, a nearly empty beer in the other.
"Can you cash this?" The man said gruffly, stepping out of the way to let you pass. You gently took the paper and scanned it, counting out two hundred and twenty-five dollars in front of him. "Is it still happy hour?"
"Right up until we close!" You answered, watching as he downed the last drop and put down the empty bottle. He handed you a five, and you grabbed him another, twisting it open with your sleeve. "Here you go!"
"Thanks," he said, heading back to the machine he had occupied for the past few hours.
Sometimes it was hard to watch people throw their lives away. You frequently saw alcoholism and gambling addictions, even drug addictions a lot of the time. You had lost count of how often you cleaned substances off the back of the toilet or found needles in the trash.
Downsides of working in a shitty dive bar.
You made a few more drinks and billed out some guests before you started your close, getting ready to do last call in a few minutes.
You tried to hide your displeasure as you heard someone new enter the bar, and you stood to face them with a smile.
You knew you made a face when you saw him. You usually had control over your expressions with a practiced eased, but he was just so beautiful, you faltered for a moment.
You hadn't dated anyone for a very long time, not since your high school sweetheart cheated on you. You no longer had trust for men.
But something about him was... different. The way he dressed, the way he carried himself. He was not to be ignored.
You snapped yourself out of your thoughts when you realized you'd been staring for too long.
"How are you doing tonight, honey?" You chirped, your smile real this time as you heard his voice.
"I'm just wonderful, how about you?"
"Funny, I'm pretty wonderful myself. What can I get you tonight?" You almost forgot to add, "oh, and I'm doing last call soon as well, we close in twenty!"
"No problem. I just need a whiskey. High shelf, on the rocks." He pointed to the most expensive bottle you had. To be fair, it wasn't that expensive, but for this kind of bar? Nobody ordered it.
You placed your hands on the barback and hopped up, grabbing the bottle you needed before dropping back to your feet.
"Single or double?"
"Double," he said in that intoxicating, raspy voice. "I had a long day."
"Yeah?" You prodded as you poured up the liquor and handed it over the bar. You leaned your arms in before you continued, "what happened?"
"Nothing you want to hear about," he said, and you heard the darkness in his tone.
"Try me," you retorted with a smile. "What's your name, honey?"
"Chuck."
"Just Chuck? I expected Van Williams the third or something fancy," you laughed.
Chuck took a sip of his drink. "Do I seem that pretentious?"
"Nah, you're just wearing a very expensive suit to hang out in a bar where everyone else is in sweats," you answered.
"You're not in sweats," he retorted, and this time he laughed. It seemed bittersweet, like he was sad under all the pain.
"No, I suppose I'm not," you agreed.
There was a few beats between when he spoke next, as if he was contemplating what words to use.
"My girlfriend slept with my uncle." He declared, his eyes not leaving your gaze once. "She said it was to help me, but I still broke up with her. He was the one person I couldn't forgive her for."
"I'm so sorry, honey." Was all you could say in these situations. Certainly not the worst thing you'd heard, not even close. In your job you listened to tales of grief, pain, and loss. You listened to crimes committed, lies told, and everything in between. The human race tended to just experience tragedy after tragedy.
You wished there was more you could do to help people, but you barely got by yourself most months.
Chuck shrugged, "don't be. I wasted a lot of time on that woman, now I can start fresh and find the real one."
He thought so logically, you were impressed. Most would let their hearts dictate how they felt after something like that, but not him. He just became all the more interesting.
"So what brought you here then?" You pressed.
"I told you, I'm starting fresh. I think I need to purchase a new venue. This one is looking promising." At some point he had finished his drink without you even noticing. It was rare you were interested in a conversation, but you stopped to pour him another anyways.
You laughed, "I can't imagine just buying a place. A little out of my price range."
"Why do you work here?" He asked suddenly, and you frowned. That was a new one. You had people asking about your schooling, tell you that being a bartender wasn't a real job, all of it. But nobody ever asked that.
You swallowed, debating if you were going to open up to him. "My best friend and I got jobs here when we first turned of age. When I..." you paused. "When I lost her, I couldn't let go of this job. So here I am."
Chuck nodded at you. "Fair enough. You're here full time?"
"I close seven nights a week," you tried to muster up a smile. You remembered how exhausted you were, and you turned your back for a moment to take a gulp of your energy drink.
When you turned back, Chuck was gone, and a hundred dollar bill lay under his empty glass. His two drinks were only twelve dollars each, that was a massive tip.
You shot down the thought of him being your boss immediately, knowing you shouldn't get your hopes up about something that would never happen.
He just seemed so... genuine.
Why did he leave like that?
~
It was two weeks before you saw him again.
He ordered the same drink, double top shelf on ice and sat quietly in his barstool while he waited for you to finish counting your lotto cash. When you were done, you turned to him with a warm smile.
"How are you tonight?" You asked.
Chuck, yes you actually remembered his name, pondered his answer. "I can't complain. Just waiting for some financials to go through for my newest project."
"You mean this bar?"
"So you remember me," he said. "Yes, this bar. Seems like it could use an extra bartender so we can get this place busy again. How does some help sound?"
It actually sounded great. You were exhausted, and being able to take a night off would be a dream. You could pick up the extra hours another day. "Good luck getting people in here," you finally answered. "My boss has been trying for years, longer than I've been here. Nobody is interested."
"That's because you're advertising the wrong thing," Chuck stated.
"And what would the right thing be?"
"The experience, of course. Coming in to an old school bar with a pretty bartender who talks to you is most people's dreams. You just haven't capitalized on the right clientele." He sounded so sure of himself when he spoke, like he knew this world better than anyone.
"I would like a change in the guests that come around," you admitted, blinking slowly as you dreamed of a night off. You shoved the thought away and smiled, "though I guess you're a nice start."
Chuck laughed. It was an intoxicating sound, a deep yet gentle chuckle. You wanted to make him laugh a million times over just to hear it again. "I appreciate the honesty. I hope I get more of it when I own this place."
You rolled your eyes, "I'll believe it when I see it."
"Fair enough." He pulled out a hundred dollar bill and left it as he took the last sip of his beverage. "Have a good night, (Y/n)."
You didn't remember telling him your name.
~
He disappeared again, this time until you nearly forgot about him. It was only when the owners, Jim and Helena, came in to talk to everyone that you remembered.
"We have decided to sell Lost City and Hidden Gem," Jim announced, clearing his throat when the room broke out in whispers.
The restaurant and the bar? That was... why? You couldn't help but remember the man at the bar, claiming he would buy the place that wasn't for sale.
"It wasn't an easy decision," Helena continued, her voice shaking. "We've been assured none of your jobs will be disrupted."
This was shocking news. They always claimed they would never sell, they built this place from the ground up by themselves as a young couple. Everyone knew the story. From rags to... well, lower middle class. Better than what you lived in, you supposed.
"The new owner will be in later today to fill you in on more details. For now, you're closed." Jim finished, clapping his hands on his thighs. "Good luck with this new chapter, it's been a pleasure."
With that, the pair walked out, leaving you all with mouths gaping, unsure what the next step was. Did you stay? Go home? You supposed you needed to wait to meet the new owner... or perhaps see him again.
~
Over the next few months, Chuck Bass made good on his promise. He changed just about everything, even upped your pay a dollar. Well, everyone's, but the sentiment was the same.
He was the best boss you'd ever had. He hired staff slowly, hand picking who he thought would match his vision best. You were currently out clubbing with one of the new hires, a tight little black dress to contrast her red skirt-white shirt combo.
Dakota was beautiful, and just your type of person. Fun, laid back, and always down to drink and have a girls night.
You swayed your hips to the music, your hand thrown in the air carelessly while the other cradled your drink. You had been doing apple pie shots all night, and you were pretty loaded.
Two men on the dance floor approached you, one heading to grind against Dakota while the other reached out to grab your hand and spin you. You giggled as you went around, your head spinning with you.
"You look good," the man shouted to you, and you blushed. You hadn't been out with a man in as long as you could remember, not since the last one shattered you.
But a little fun couldn't hurt, right?
"Not so bad yourself," you replied as you turned around and dropped it down to the beat of the song. You danced like that for what felt like hours, grinding and teasing each other in a way only strangers could.
When your drink was empty, you excused yourself to find Dakota and head up to the bar. After a few minutes of searching, you realized she was nowhere to be found. You dug through your purse to pull out your phone, where she had left you a message.
Have fun! Went home with a mans. Don't worry about me.
You furrowed your brows and set down your empty solo cup, sighing as you opened uber. You didn't like being out alone, it wasn't always the safest, especially when you were drunk. You booked a car, and glanced at the ETA.
Fifty-four minutes!? What the hell!? You couldn't wait that long, the club closed in forty-five. You began to panic, how were you going to get home? You headed for the door and exited the noisy club, the nighttime chatter outside a stark contrast.
The breeze was cold on your legs as you scrolled through your contacts hopelessly, knowing there was nobody to pick you up with Dakota gone. You were a little annoyed she had just abandoned you like that. Without even so much as a goodbye?
You stopped when you saw his name. It was two in the morning, far too late to be calling your boss to pick you up from a club.
Yet, when you clicked his name and pressed dial, you weren't sure what came over you. It rung only one and a half times before his soft voice picked up.
"What can I do for you, (Y/n)?"
He had your number programmed into his phone.
"I'm at Redrock, can you come get me? The uber is an hour away and Dakota left me and I just wanna go home," you rambled, word vomit spewing out of your mouth.
He didn't even pause before he answered, "I'm on the way."
The alcohol from your last drink must have hit right around then, because the rest of the events of the night were gone from your memory when you awoke the next morning.
In a bed that wasn't yours.
You shot up and looked around frantically, hoping to see something you recognized that would tell you where you were. You vaguely remembered calling Chuck to come get you... there's no way you stayed in his home last night.
Yet, the expensive decorations and thousand-thread-count sheets told another story. Perhaps it was a spare bedroom? It didn't look very lived in, after all, more like somewhere for emergencies. The walls were decorated, yes, but generically with paintings of the woods and ships and landscapes. Nothing clearly personal, no books, no computer, nothing that said someone actually lived in this room.
You concluded you did not sleep with your boss last night.
A pang of disappointment surprised you at that thought. Would you want to be with Chuck? You shoved the thought away. You knew who he was now, the Charles Bass. About as rich as rich gets. And you barely made ends meet.
Although, you'd been doing much better financially since he had taken over the building. Both sides were busy, he had to hire more kitchen and front of house staff. Your dying job was thriving for the first time since... well, since you had lost your best friend.
There was a knock at the door as you started shifting around in the bed, making noise with the comforter as you tore it off to stretch yourself out. You realized your head was pounding and every muscle in your body was sore. You groaned and mumbled something to the door, which Chuck took as an invitation to open it.
"Good, you're up. I was starting to worry. How do you feel?"
A million questions flew through your head as he spoke. Why did he bring you back here? What had happened last night? Why hadn't he dropped you off at home? Had you said something?
"I hurt, but I'll survive. What happened when you picked me up?" You left a few beats of silence between your sentences.
"You said you didn't want to be alone in your apartment, so I brought you back here. You said some... interesting things, but I eventually got you to bed." He laughed, and you were glad you couldn't remember as your face heated up.
Why were you such an idiot when you were drunk? Why had you called him of all people?
You supposed you didn't really have anyone else.
"I'm sorry. It's just, after Dakota left-"
"No need to apologize," he cut you off. "It's my pleasure."
~
You wished you could say the next few weeks went on without incident, but that would be a blatant lie.
Between the flirty comments, light touches, and him standing far too close to you, something had shifted that night. He made his intentions far more clear, and if there was one thing you were learning about Chuck Bass, it was that he generally always got his way in the end.
He had also promoted you to Lost City supervisor. Jim and Helena had never allowed you to work at Hidden Gem, they said you weren't 'family friendly' enough. Chuck did not share that opinion, but you still remained over at Lost City once you got your promotion.
This time it was of your own choice, however, which felt much better.
You and Dakota had made up after a heated conversation, and she apologized for abandoning you like that. You had hung out since, you just hadn't gone drinking again.
Your clientele had changed, exactly as Chuck had promised it would. You actually enjoyed the conversations you had now, not having to listen to hopeless stories of poverty, addiction, and losing everything. A higher class of people began to come in, spending more money and getting less fucked up.
They ordered cocktails and wine, something you had never really served before. They ordered off the new menu, pub food upgraded from the simple happy hour menu you had before. You now had fish and chips, nachos, mozza sticks, all sorts of meals to choose from.
And wow did the guests tip well, especially on the VLT's. Every couple hundred won, you'd get at least a twenty slipped across the bar for you. You had never thought you'd be happy again, not at work, not without her.
But Chuck had changed everything.
It made you wonder; just how much of your life was going to alter now that he was forcing his way into it?
Though you supposed it wasn't really forcing if you let him.
For he had also let you claw your way into his routine, picking you up to bring you home from work every night. It sure beat the walk in a sketchy neighbourhood in the wee hours of the morning.
You became comfortable together, chatting and hanging out like old buddies. You had much more in common than you thought you would, and you were slowly falling for him.
This time, when you thought of a happy future, you let yourself dream instead of shoving the thought away.