When the Check Splits the Date
A mismatched couple meets for a first date, but what should be a night of excitement turns into a masterclass of cringe.
Story Transcript
The following is Based on true events.
The seafood restaurant in Boston buzzed with ambient chatter, the hum of conversation bouncing off the wooden walls and dim lighting. It was the kind of place where most diners’ attention remained focused on their tables, insulated by their own little bubble of conversation, but not the man seated alone at a booth just within earshot of a couple who’d just arrived. Waiting for his own dinner companion, he felt his attention drifting toward them—a man and woman, seemingly on their first date. They had the unmistakable look of two strangers sizing each other up. Something about them seemed... mismatched.
The woman, seated directly to his left, shared his booth but with a separate table. She was young and elegant, with just a touch of makeup and wide eyes that sparkled with polite optimism. The man across from her was a heavier-set guy with a red beard, dressed casually, nursing a whiskey cocktail before the date had barely started.
As he sipped his drink, the woman’s glass of wine was mistakenly brought early, despite her request to have it with her meal. She chuckled, brushing off the error, though a slight hint of nervousness tinged her voice as she pushed through small talk with him.
“So,” she began, “I have to be honest. I’ve never gone out with someone from an app before. I’m not all too familiar with how things like this go.”
He nodded without looking at her directly. “I’ve been on a lot of these.”
A pause followed his blunt response, and the woman’s optimism took a slight hit, but she continued. “That’s nice!”
Silence again, hanging awkwardly between them. The observer, idly watching as he waited, began jotting down their conversation—a habit he’d picked up over the years, like doodling but with words. There was something about this exchange that felt like it might turn into a train wreck, and he found himself involuntarily drawn in.
The woman gave a polite smile, grasping for a conversational lifeline. “So, was there anything you wanted to know about me?”
“Sure,” he shrugged, swirling his whiskey. “Like what?”
She hesitated. “I mean—never mind. So, uh, what’s the difference between a journeyman plumber and a regular plumber?”
“Not much difference, really,” he muttered.
“Oh.” She nodded, trying to feign interest. “Well, I had to go to school for four years, you know, to get my degree, for my job. I always thought it was so cool how some people just got right into working.”
The man stared at her blankly. “I have a degree.”
Her eyes widened a bit, genuinely surprised. “Oh, that’s cool! What in?”
“Communications.”
“Really?”
“Yeah. What?” he shot back defensively.
She seemed taken aback by his tone. “That just… caught me a little by surprise. Only because you’re now working in plumbing, I mean.”
“Sure do.”
She glanced down at her glass, carefully choosing her next words. “You know, I get nervous on first dates sometimes, and I can talk way too much. Don’t hesitate to jump in.”
“You’re fine,” he replied, barely looking up from his drink.
The observer stifled a chuckle. If the man had a roadmap for keeping a conversation at a low simmer, he was following it to the letter. From the woman’s repeated attempts to engage, it was clear she was trying to create some sense of connection, but he wasn’t giving her much to work with.
A few minutes passed, the woman trying various conversation topics with little success. She seemed like the type who was used to reading the room, but here, it was as if she was speaking into an echo chamber. With a faint smile, she pressed on.
“So, have you lived out here your whole life?” she asked, hoping to find a shared background.
He nodded. “Whole life.”
Her gaze brightened, encouraged by the smallest indication of engagement. “When people ask me where I’m from, I’m never quite sure how to answer because I actually grew up on a houseboat and—”
The man interrupted, a flicker of interest sparking. “Is that why you picked a seafood place?”
She laughed, surprised by his sudden attempt at humor. “Oh, haha. That’s a good one. I’ve never gotten that one.”
He stared at her blankly, face devoid of expression. The light in her eyes dimmed a notch.
“Uh, no,” she added after a moment. “Actually, my family doesn’t know the first thing about fishing. My parents are marine biologists. They basically research whales. Like how George pretended to on Seinfeld, but for real. So we were—”
“You can eat whales?” he interrupted, his brow furrowing slightly.
Her smile faded, replaced by a look of genuine concern. “Uh… No.”
“Oh.”
She looked down, swirling her wine glass, clearly contemplating an exit strategy. “Are you feeling alright?” she asked, her voice gentle. “If this isn’t a good time, or if I said something that rubbed you the wrong way, we can do this some other time.”
He waved her off. “No, you’re fine.”
She forced a faint smile. “Alright.”
The observer could see the weariness starting to creep into her posture. She seemed to rally herself, though, taking a deep breath and diving back in. “Funny story,” she began, a hint of determination in her voice. “I actually studied something different from what I ended up doing for work, too. I majored in physics and only minored in music because I wanted accountability so I wouldn’t forget how to play the piano. But I enjoyed it so much I thought, ‘Why not take a year and just do music stuff?’ And, well, the rest is history.” She smiled, her eyes lighting up. “If you’d told me I’d be a professional musician ten years ago, I’d have laughed at you.”
The man stared at her blankly for a moment before asking flatly, “What kind of money you make doing that?”
She blinked, caught off guard. “Excuse me?”
“What kind of money you make doing that?”
“Oh, you know,” she said after a pause, clearly thrown. “It… varies.”
“That’s what I figured,” he muttered, his gaze falling back to the menu.
The woman, visibly deflated, took a sip of her wine and glanced away, her attempts at conversation hitting wall after wall. The observer noted the shift in her demeanor, the light-hearted warmth from earlier giving way to a muted resignation. The woman, it seemed, had expected a date, a pleasant evening of getting to know someone new, but the man was as inviting as a closed door.
She cleared her throat, trying a new angle. “Have you been watching anything good on Netflix lately? I’m re-watching some of my favorite shows from growing up, and seeing them now, at a different stage in life, is kind of interesting.”
The man, uninterested, squinted at the menu. “Anything look good to you?” she asked after a pause, trying to draw him back in.
“Not really,” he grumbled. “I’m gonna see if they can just do a regular burger.”
“Oh,” she replied, clearly taken aback. “I apologize. I should have checked if you like seafood.”
He shrugged. “I do. This stuff’s just overpriced for the area.”
She laughed awkwardly. “Oh, I wasn’t expecting you to pay.”
“So you’re paying? Cool. Maybe I’ll get something else, too.”
Her laugh died instantly. “Haha.”
He looked at her, brow raised. “What?”
“Oh, you’re—” She stopped herself, clearly straining for grace. “You were making a joke, right?”
The man blinked. “What joke?”
A flicker of resolve crossed her face. “I meant I didn’t expect you to pay for my half.”
“Oh.”
It was as if the man had unknowingly, and repeatedly, defused every attempt she made to breathe life into their exchange. The woman finally fell quiet, her fingers lightly tapping her glass as she watched him peruse the menu. It was then the observer realized she was truly done. The enthusiasm was gone, replaced by a polite resignation.
After a few long, silent minutes, she excused herself. “Actually… I think I might have to call it a night.”
He looked up, seemingly unaffected. “Oh. Okay.”
She stood, offering a faint smile. “I’m just going to go pay for this at the bar.”
“Okay.”
The observer watched as she walked away, her back straight, carrying a quiet dignity. The man, meanwhile, settled back in his seat, eyes on the menu. He flagged down a waiter as she approached the bar, paying for her wine without another glance back at him.
As the observer sat in his booth, he couldn’t help but reflect on the scene he’d just witnessed—a first date that would likely also be the last, a meeting that seemed to reflect the emptiness of modern dating, where two people could sit across from each other yet be miles apart.
And as he scribbled a final line in his notes, he wondered: how many dates in the world were ending just like this, in small restaurants and bars, with barely a spark between them?
Part Two:
As the woman returned to the booth to gather her things, she glanced at her date one last time, possibly hoping for some sign of enthusiasm or appreciation. But his gaze remained fixed on his half-finished whiskey, oblivious or indifferent to her disappointment. She seemed to steady herself, a hint of determination sparking in her eyes as if deciding to salvage whatever dignity the night had left her with.
Taking one last sip of her wine, she attempted to steer the conversation into a more neutral topic. “So,” she began, as casually as she could manage, “besides work, what are some of your, you know, interests? Any hobbies?”
He paused, as if weighing whether to respond at all, before answering with a single word: “Sports.”
Her face brightened slightly. “Oh, I like sports too! Do you play?”
The man shrugged, looking at her with mild confusion. “Not anymore. I had a moment back in high school. Would’ve gone pro if that had been what I wanted.”
She nodded politely, clearly unsure how to respond to his lack of enthusiasm. “That’s… that’s interesting.” She hesitated, likely searching for some common ground or a way to engage him further. “You know, I find it so fascinating how people can stay connected to things they loved as kids, like sports or music. For me, it was music—I majored in physics, but I minored in music because I just couldn’t let it go. I even took a year after college just to focus on it. Crazy, right?”
The man didn’t even look up. “Uh-huh.”
Undeterred, she continued, more to herself than to him. “So, if you were on a desert island and could only bring one book, which one would it be?”
He looked puzzled, clearly missing the point. “I’ve never been to the desert or anything. I kind of like to stay close to home.”
The observer stifled a laugh, marveling at how the man managed to miss the spirit of every question. The woman gave a small, resigned smile, her patience clearly wearing thin. She glanced at her watch, the polite excuse of needing to leave seeming to hover on her lips. But instead, she took a long breath, maybe holding out hope that the evening would improve.
For a moment, there was silence, just the clinking of glasses and quiet conversations filling the restaurant. Then the man muttered something about the “overpriced seafood” again and shifted in his seat. She glanced around, perhaps deciding that if he wasn’t going to make an effort, she would match his indifference.
“I’m not super hungry,” she said lightly, signaling that she was nearly ready to call it a night. “I might just stick with my wine.”
“Okay,” he replied, his gaze shifting lazily to the menu. “I’ll hurry up and order then. Service here is mad slow.”
She smiled tightly. “I apologize for picking the wrong place.”
“No big deal,” he muttered. “I’m just gonna see if they can do a regular burger.”
The woman took a breath, a faint shadow of irritation flashing across her face. She tried to shrug it off with another attempt at humor. “I wasn’t expecting you to pay,” she said, smiling to soften the statement. But he took her words literally.
“So, you’re paying?” he asked with a look of genuine interest. “Cool. Maybe I’ll get something else then.”
She faltered, the remnants of her smile slipping away. “Haha… what?”
He stared at her blankly. “What?”
“Oh, you were…” She paused, letting out a resigned sigh. “Never mind.” She looked away, her fingers tracing the rim of her wine glass. Whatever spark or optimism she’d brought to the table had been snuffed out, leaving only a quiet resignation.
As she sat, watching him scan the menu one last time, she subtly gathered her purse, her decision already made. The man, blissfully unaware, seemed more interested in the slow service than in her silent withdrawal from the evening.
The observer, who had now spent nearly thirty minutes witnessing the excruciating ordeal, felt a pang of empathy for the woman. He could see her weighing her options, mentally rehearsing her exit. And when she finally cleared her throat and leaned forward, he knew the time had come.
“Actually, I think I might call it a night,” she said softly.
The man looked up, expression blank. “Oh. Okay.”
She offered him a polite but hollow smile. “I’m just going to go pay for this at the bar.”
He nodded, as if her departure was nothing more than a minor inconvenience. “Alright.”
She stood, straightened her shoulders, and walked away with a grace that belied the awkwardness of the evening. Her face held a quiet dignity, the kind that comes from making peace with a disappointing experience. She headed toward the bar, taking her wine glass with her, and began the process of settling the bill alone.
The observer watched as she exchanged a few polite words with the bartender, smiling as though she hadn’t just spent the last hour trying to wring some semblance of connection from an uninterested man. When her card was handed back, she thanked the bartender, then glanced back toward the booth one last time. The man was still seated, his gaze fixed on his phone, entirely unaware of the finality of her departure.
As she stepped outside, a slight chill crept into the restaurant from the open door, as if marking her absence. The man, oblivious, flagged down a server and ordered his “regular burger,” then settled back to wait, unfazed by the date that had just ended.
The observer turned back to his notes, jotting down a final line: Some dates end before the check arrives. He tapped his pen against the table, reflecting on the story he’d just recorded. In the vast landscape of modern dating, it seemed, there were those who arrived with openness and optimism, and others who, like the man, simply showed up.
Part Three:
As the man returned to his booth after placing his final order, the observer set his pen down and took a moment to absorb the scene. The couple’s mismatched energy still lingered in the air, like a faint echo of a conversation cut short. The observer leaned back, his gaze drifting to the empty seat where the woman had sat only moments ago, and a quiet realization crept over him.
It wasn’t just about this couple—the awkwardness, the mismatched intentions. It was something broader, a shift he’d been noticing lately. People, especially young people, seemed to be going through the motions in these strange, disjointed encounters, more disconnected than ever before. And perhaps what he’d just witnessed was the most exaggerated version of this trend.
The woman had come in with warmth, openness, and a genuine curiosity. She’d shown patience, empathy, and resilience, trying to make the evening enjoyable despite the lack of response. But the man, with his guarded demeanor, his disinterest and apathy, seemed to embody a kind of emotional detachment that the observer found both intriguing and unsettling.
It wasn’t just that he was rude or indifferent—it was as if he was sleepwalking through the date, simply fulfilling an obligation with no intention of truly connecting. The observer wondered if this was a symptom of something larger, a sense of disillusionment that ran deeper than this single encounter. He thought of all the times he’d overheard similar conversations, dates where one or both people seemed to have already mentally checked out, and he began to see a pattern. Maybe this was part of a new reality for dating, where real connection was becoming a rare commodity.
His own dinner companion arrived shortly after, and he gave her a warm smile, grateful to have someone who was fully present, someone who would engage in the evening without pretense or distraction. They ordered, exchanged a few jokes, and shared a quiet toast—an acknowledgment of the simple pleasure of being in good company.
But even as he enjoyed the meal, a part of him kept circling back to the couple, the momentary glimpse he’d had into the complexities of modern romance, or perhaps the absence of it. He found himself quietly promising to stay attentive, to never let his own dates devolve into something as empty as what he’d just witnessed.
For the rest of the night, he kept the woman’s dignified exit and the man’s indifference in mind, a reminder of how easy it was to be physically present but emotionally absent. And as he and his companion shared stories and laughed, he made a silent vow to always bring something to the table—to listen, to engage, to connect.
It was a small reminder that while dating could be messy, awkward, and even discouraging, the real moments—the ones with warmth, depth, and shared vulnerability—were still worth striving for.