Second Seat at the Bar

Johnny Reyes had lived most of his thirty-four years quietly in the background. In college, he was the roommate who proofread essays and fixed laptops while his friends pursued relationships and adventures. At work, he was the quiet software developer who cleaned up messy code bases without taking credit, who trained new hires without the title of “senior” beside his name.

Second best. Second choice. Always close, but never the first name on anyone’s list, is how he always felt.

He told himself he was fine with that. Someone had to carry the unseen weight. But late at night, when the glow of his computer monitor gave way to self reflection, he admitted to himself that he wanted to be chosen, just once.

When he wanted to unwind he was more of a coffeehouse and bookstore kind of man, the kind who admired a well poured latte like a piece of art. But the first night he stumbled into Bar Calypso after a brutal week of debugging, he saw her.

Cassandra.

She was behind the bar, her chestnut brown hair pulled back in a loose braid, a silver angel pendant swinging at her collar as she shook cocktails like a practiced magician. Her smile seemed to scatter across the room like sparks from a bonfire. The men at the bar leaned closer when she spoke, and she handled them all with charm and wit.

Johnny, awkwardly ordering a whiskey he didn’t really want, found himself stunned when she lingered with him.

“You’re new here,” she said, sliding his glass over. “First drink, first story. Them’s the rules. So, what’s yours?”

He stammered at first, but then words flowed out the way they rarely did for him. They talked about the absurdity of technology, the rhythm of beach city life, the way people pretend to be busy when they aren't. She didn’t just listen; she volleyed back with insights that stuck with him for days.

From that night on, Bar Calypso became his second home.

He told himself it wasn’t about her. It was about routine, treating himself, breaking from monotony. But each evening he walked in, scanning for the sheen of her braid, the sweep of her voice across the bar. Each time, they picked up conversations with the ease of old friends.

Johnny convinced himself there was something real there. But he couldn’t ignore the others. The smooth talking guys in tailored suits, the frat boys with crude jokes she laughed at, the ones she invited to join her at after hours dinners or clubs.

Johnny sat with his whiskey, smiling politely, slipping back into that familiar shadow, second choice.

Determined to change that, Johnny began to build a new routine.

At first, it was subtle. A haircut that wasn’t his usual rushed trim at the strip mall barber, but something sharper, styled with a dab of pomade. Then came the gym membership, the personal trainer who barked encouragement at him. He downloaded a dozen “art of manliness” podcasts with tips about eye contact, teasing banter, and how to command your space.

He hated the way their tips made women sound like puzzles that could only be solved by men who acted in certain ways. But something in Johnny clung to the hope that if he learned enough, tried hard enough, maybe Cassandra would finally see him the way he saw her.

After work, he would change into one of his new button downs and head to Bar Calypso. He tipped generously, sometimes more than he should, slipping twenties into the black leather folder with a quiet satisfaction. Surely she noticed.

And she did notice. Every night, laughing at his dry jokes, matching his obscure references about history or linguistics. Once she told him about her grandmother’s garden, about quinceañeras that stretched until sunrise, about her life aspirations. Her voice softened when she spoke of her family, and Johnny felt an unbearable tenderness swell inside of himself.

But inevitably it came. The loud group of brokers slapping black cards on the bar top. The tech startup crew with stories of big breakthroughs and bigger parties. The tatted up pretty boys who clearly spent as much time on perfecting their hair as they did in the tattooer's chair. Cassandra glided toward them as if carried by their current. Johnny would sit with his empty glass, watching her throw back her head in laughter, give out her number, then vanish into the night with them.

He told himself not to take it personally. Networking was an important part of making a customer a regular patron at a bar. And it’s the bartenders job to make everyone feel seen.

“Besides, you’re still building,” he muttered to his reflection one night in the gym locker room. “You’ll get there.”

He took on freelance coding work after hours, the money flowing straight into an account he jokingly labeled “The Cassandra Fund.” He day dreamed about using it to take her out to five star restaurants, and trips to anywhere in the world. He began practicing his walk, his entrance into a room, and his opening lines to conversations. He was determined to become the man who couldn’t be overlooked.

Each attempt to close the distance collapsed under bad timing. He’d steel himself to ask her out, only for someone else to swoop in. He’d lean toward her to suggest dinner, only to hear her already making plans.

And still, Johnny returned, night after night, his hope bruised but not extinguished. Because when she turned back to him, when her eyes found him across the bar, he swore there was something unspoken. He just had to keep working to be the man who deserved it.

It happened on a Thursday.

The bar wasn’t crowded, just a scatter of regulars and a few college kids. Johnny sat at his usual stool, belly up to the bar, heart buoyed by the way Cassandra smiled when he walked in. Not the usual courtesy smile, at least he told himself it wasn’t.

She teased him for his usual whiskey order, said she’d convert him to mezcal one day. He lectured on the history of distilling, exaggerating details to make her laugh. For a moment, it felt like the whole place had shrunk to just the two of them.

Then the door swung open, and in walked a man who looked like he had stepped straight out of one of those dating guru feeds Johnny scrolled through at night. Tall, sculpted jaw, a suit that whispers wealth. He didn’t so much enter the bar as claim it.

Johnny’s stomach dropped when Cassandra yelled out his name.

“Victor!” She slid out from behind the bar to rush up to hug him. The man kissed her cheek, and murmured something inaudible that made her laugh in that unguarded way Johnny had convinced himself was theirs alone.

Victor ordered a bottle of champagne. And soon Cassandra was perched beside him, glass in hand, her braid brushing against his shoulder.

Johnny sat frozen, his whiskey untouched. He felt the familiar ache rising. He had been so close. But here he was again, second best. Always second.

Then something inside him snapped. Not anger, not bitterness, something harder, more desperate. He couldn’t keep watching her light drift toward everyone but him.

When Victor excused himself to take a phone call, Johnny slid off his stool. His heart was racing, and palms damp, but his resolve pushed him forward until he stood beside her. Cassandra turned, then smiled, a little confused.

“Hey, Johnny. Need another drink?”

“No.” His voice cracked. “I need to say something.”

She tilted her head, curious. “What’s up?”

The words tumbled out faster than he planned. Weeks of swallowed hope all flooded out at once.

“I like you. I think about you all the time. I come here because when I talk to you, you make the world feel less heavy. Because you’re smart, funny, kind, and I…” He caught his breath, “I want to take you to dinner, a movie, a walk on the pier, anything. I want to be with you. Not as a customer, or a friend, but something more.”

The silence grew heavy as it spread between them, only broken up by the clink of ice in glasses.

Cassandra’s smile faltered. Her eyes softened, but not in the way he hoped for.

“Johnny…” she said, as she gently touched his hand, “You’re a good guy. But I don’t feel that way about you. I’m sorry.”

The words shattered something inside him, like bricks thrown through glass. Shaking his head, he said, “But, I can be better. I can do better. If you’d just give me a chance.”

“Johnny.” Her voice firmed, not unkind but unmovable. “It’s not about you needing to be better. You’re already great. I just don’t have those feelings for you. Please understand.”

He wanted to argue, but the finality in her tone made it clear. No room for negotiation. No “maybe later.”

He nodded, stepping back as though the ground beneath him had shifted. “Okay. I get it.”

But he didn’t get it. Not even a little bit.

Not as he turned to leave. Not as Victor’s laughter filled the room behind him.

For the first time in months, Johnny didn’t finish his drink. He just walked toward the door, heart aching with the truth he had spent so long trying not to see.

The night air outside Bar Calypso was thick with the smell of rain on hot asphalt. Normally, this was one of his favorite scents, but somehow it added weight to the feelings he was overwhelmed with. Once out the door, Johnny shoved his hands deep into his jacket pockets and leaned against the wall. His eyes fixed on the cracks in the sidewalk. Each breath felt jagged, scraped raw by Cassandra’s gentle refusal.

He replayed the moment again and again, like a broken loop of code he couldn’t debug. Her eyes set like stone, her words soft but final. You’re already great. I just don’t have those feelings.

For the first time in his adult life, the thought of going home to his small, silent apartment felt unbearable. He decided to walk in the rain until he could no longer walk.

“Rough night, Johnny?”

The voice pulled him back. He turned to see Ashley a few feet away, leaning against the bar's side door, her black apron still tied around her waist.

She was Cassandra’s opposite in nearly every way. Where Cassandra had the polished elegance of a tall, striking, Vogue cover model, Ashley carried her petite frame with a kind of irreverent ease. Short-cropped blonde hair matched the mischievous tilt to her grin. Her signature big black boots went well with the jumbled mix of small tattoos peeking out from under her rolled-up sleeves.

Johnny cleared his throat and tried to straighten up, to pretend nothing had happened. “I’m fine.”

Ashley arched a brow, clearly unconvinced. “Right. You storm out without finishing your drink, looking like someone just told you your puppy died, now you’re just holding this wall up with your back, and you’re fine. Sure.”

He sighed, shoulders sagging. “I just majorly embarrassed myself, that’s all.”

Ashley stepped closer, leaning against the wall next to him, her voice softening. “You told Cassandra how you feel.”

Johnny blushed furiously. “How did you know? Oh, God, you heard us, didn’t you?”

“Please.” She smirked. “I was standing ten feet away pretending to wash beer glasses. Half the bar saw. But don’t sweat it. That type of thing happens all the time. People shoot their shots. Sometimes they hit the target, sometimes they don’t.”

Her tone wasn’t mocking, just matter of fact. Still, Johnny winced. “Yeah, well. Guess I should’ve known better. That was stupid of me.”

Ashley tilted her head, studying him. “Why? Because you’re not Mr. Champagne bottle and Brooks Brothers suit guy in there?”

The bitterness in his laugh surprised even him. “Pretty much.”

“See, that’s your problem,” Ashley said, crossing her arms. “You think women only want guys like Victor. Slick, flashy, extra superficial. You don’t get that plenty of us would take smart and gentlemanly over shallow and shiny any day.”

Johnny looked at her, uncertain. “That’s not how things seem to work, not what I’ve seen, at least. You’re not just screwing with me, are you?”

Her grin sharpened, turning playful. “Depends. You asking me out?”

His eyes widened, heat rushing to his face. “I, wait, what? No, I mean, are you being serious right now?”

Ashley chuckled, the sound gentle and teasing. “Relax, Johnny. I’m messing with you. But for the record…” She leaned in just enough that he caught the faintest hint of Japanese cherry blossoms from her perfume. “If you did ask, I wouldn’t say no.”

For the second time that night, Johnny felt something shift inside him. But this time the heaviness cracked, replaced by an electric jolt of disbelief that almost made him laugh. “Now I know you’re messing with me.”

Ashley winked. “No. I am dead serious. I’ve been watching you go from hope to mope over Cassandra for months. You’re not the first, and won’t be the last one to do it. Honestly, it’s been kind of adorable, in a tragic way. But maybe it’s time you noticed there’s more than one bartender in this place.”

The words hung between them, light but charged. Johnny felt the ache in his chest easing, replaced by the vibrance of buoyant hope he hadn’t expected.

Ashley nudged his shoulder with hers, playful now. “So? You gonna keep sulking in the rain, or are you gonna buy me a burger, and prove you’ve got better taste than chasing after someone who flirts with a trust fund douche, like Victor?”

Johnny blinked, then smiled, small at first, then wider than he’d smiled in weeks.

“Yeah,” he said, the word coming out easier than he thought it would. “I think I’d like that. Let’s go.”

Ashley led the way down the block, her apron balled up in one hand, the night still humming faintly with city sounds of buzzing street lights and passing cars on rain slickened streets. Johnny walked beside her, the sting of rejection already fading in the newly discovered glow of her presence.

“So,” Ashley said, glancing sideways at him, “on a scale of one to ten, how bad do you think you did in there with Cassandra?”

Johnny groaned. “Please don’t make me relive it.”

“Oh, I’m gonna. You’re never living that one down.” She chuckled. “You were all, ‘Cassandra, you’re so beautiful, your braid is so wonderful, you’re the light of my life, my reason for living, the singular star in my…’”

“I did not say that.”

“Maybe not, but I’m close enough.”

He laughed despite himself, shaking his head. “No, but, I really was a hot mess.”

“Yeah, I could tell. You had that look like you were either about to propose marriage to her, or throw up on your shoes.”

Johnny laughed so hard that he snorted, the sound startling him with how unforced it was. “Great. It gets even worse in hindsight. And everyone in the bar was watching. Just great.”

They turned the corner, the lights from a late night diner flickering ahead. Ashley shoved the door open, as Johnny scrambled to hold it open for her. Bright fluorescent lights, oldies tunes crooning from a juke box, and the smell of frying onions and grease greeted them like old friends.

Sliding into a booth, she leaned her chin on her hand. “You know, Johnny, for a guy who just epically face planted, you’ve got some pretty good timing.”

“Good timing? How do you figure?” he echoed.

“Hey, you shot your shot with Cassandra. Bold move, by the way. A for effort. Didn’t land, sure. But you walked out into the night, and who did you find?” She pointed to herself with both thumbs in mock grandeur. “Upgrade.”

Johnny grinned, raising his eyebrows. “Pretty bold, calling yourself an upgrade.”

Ashley shrugged. “Confidence is hot. Haven’t you learned anything from watching those idiots in the bar?”

He groaned again. “Don’t remind me. Apparently I’m a slow learner.”

She chuckled, then softened, her eyes catching his in a way that felt more real than anything he’d felt before. “Seriously though, I’ve seen you changing over the last few months, you don’t have to keep trying so hard to be someone else. You’re fine as you are. More than fine, actually.”

Johnny felt the words dance through him. In them he could feel new sensations, warming and grounding. “Thanks. That’s definitely the sweetest thing anyone’s said to me all day.”

The waitress arrived, tossing down menus with a practiced thud. Ashley didn’t even look. “Two cheeseburgers with no onions, fries, chocolate milkshakes. Extra whipped cream on his.”

Johnny was perplexed. “How did you know?”

“I watch people,” she said with a sly grin. “It’s literally my job. And you, Johnny Reyes, are totally an extra whipped cream kinda guy. You weren’t fooling anyone with that glass of neat whiskey.”

He laughed, shaking his head. “Am I really that obvious?”

“Definitely,” Ashley said. “Obvious, and stubborn, but kind of cute about it.”

The food arrived, salty, sweet, greasy and glorious. Ashley raised her milkshake in a mock toast. “To second chances and second choices.”

Johnny clinked his glass against hers, smiling. “And maybe finally making the right choice.”

Ashley grinned, leaning back in the booth. “Careful, Johnny. Keep talking like that, and you never know what might happen.”

For the first time in a long while, Johnny didn’t feel like he was chasing anyone. He just laughed, the sound mingling with hers, as the night eased forward into something new.