The Invoice Date: When Chivalry Comes with a Price Tag

Chapter 1: The Brother’s Pitch

When her brother sets her up with a seemingly perfect gentleman, she’s hesitant, but gives it a shot. Flowers, charm, and a sweet smile make her wonder if he’s the real deal. When he insists on driving her home, a gut feeling whispers: Don’t. She should’ve listened.

You know when someone says they have “the perfect guy” for you? Yeah, that’s exactly how this whole disaster started, and let me tell you, it’s a story that gets better and worse with every detail I remember.

My brother Marcus had been going on about this Andy guy from his Saturday morning pickleball group for what felt like an eternity but was probably closer to three weeks. Marcus is the kind of person who gets an idea stuck in his head and then hammers away at it with the persistence of a woodpecker on espresso until everyone around him either gives in or moves to another state.

“But he’s not just any guy, Sarah,” Marcus said for probably the fifteenth time, smirking as he refilled his protein shake at my kitchen counter on a perfectly peaceful Tuesday evening that I had been planning to spend alone with Netflix and leftover Chinese food. “This Andy is polite, smart, has a good job in accounting, drives a reliable car, owns his own place, and here’s the kicker—he’s still single. Has been for way too long, if you ask me, which should tell you something about how picky he is about quality.”

I rolled my eyes so hard I’m surprised they didn’t detach from their optic nerves and roll right out of my head onto the kitchen floor. “That’s exactly what you said about Kevin six months ago, remember? The vintage spoon collector who turned out to have not just a collection but an unhealthy emotional relationship with antique silverware?”

“Kevin was a mistake, I’ll admit that,” Marcus said, holding up his hands in surrender. “But Andy’s different. There’s something about him that’s just… solid. Dependable. The kind of guy Mom would love and Dad would actually approve of.”

There was something in his voice that made me pause mid-chop. I had been massacring some poor innocent carrots for a stir-fry, taking out my mounting dating frustrations on root vegetables like any reasonable twenty-eight-year-old woman would after a string of disappointing romantic encounters that had left me questioning whether decent men actually existed or if they were just a myth perpetuated by romantic comedies and my overly optimistic friends.

Marcus wasn’t usually this persistent about his matchmaking attempts. Generally, he’d make a suggestion, I’d politely decline, and we’d move on to discussing normal sibling topics like whose turn it was to visit our parents or whether his latest workout routine was actually working or just making him more insufferable. But this Andy character had captured his attention in a way that was both touching and slightly concerning.

“Look,” Marcus continued, setting down his protein shake and leaning against my counter with the earnest expression he’d perfected during his high school debate team days, “I know you’ve had some bad experiences lately. Hell, we all know Kevin was a disaster waiting to happen from the moment he started explaining his spoon grading system. But I really think Andy could be different. He’s been asking about you ever since I mentioned I had a sister who was single and successful.”

Here’s the thing about brothers: they never give up when they think they’re helping, even when their help feels more like friendly torture. I’d honestly had enough of “nice guys” with hidden expiration dates—men who seemed perfectly normal until they revealed their secret obsessions with model trains or their inability to eat food that wasn’t beige or their conviction that women should split every check down to the penny while simultaneously holding every door.

But something about Marcus’s tone, the way he looked so genuinely hopeful and invested in this potential setup, wore down my resistance like water eroding a stone. Maybe it was the fact that he’d driven forty minutes across town to have this conversation in person instead of just texting me about it. Maybe it was the way he talked about Andy with the same enthusiasm he usually reserved for discussing his fantasy football lineup. Or maybe I was just tired of being the perpetually single woman at family dinners, fielding well-meaning but increasingly desperate questions about my love life from relatives who seemed to think being unmarried at twenty-eight was some kind of personal failing that required immediate intervention.

“Fine,” I said finally, setting down my knife and turning to face him with what I hoped was an expression of resigned acceptance rather than complete surrender. “One date. Just one. And if this turns out to be another Kevin situation, I’m done with your matchmaking forever. No more suggestions, no more helpful hints about guys from your various sports leagues, no more casual mentions of single coworkers. Deal?”

Marcus’s face lit up like I’d just agreed to donate a kidney to save his life. “Deal! You’re going to love him, Sarah. I really think this could be the one.”

Famous last words, right? I should have known right then that any sentence beginning with “you’re going to love him” was basically an omen of romantic disaster. But I was trying to be open-minded, trying to give love a chance, trying to prove to myself and everyone else that I wasn’t impossibly picky or emotionally unavailable or whatever other explanations people offered for my single status.

So there I was the following Saturday evening, standing in front of my bedroom mirror at six forty-five, adjusting my dress for what had to be the fifteenth time in the past hour. I’d chosen a simple navy blue dress that was nice enough to show I’d made an effort but not so fancy that it would send the wrong message about my expectations for the evening.

Why do we do this to ourselves? I mean, what’s the point of trying to look perfect for someone we’ve never met, someone who might turn out to collect belly button lint or have strong opinions about the proper way to load a dishwasher or think that pineapple on pizza is a moral failing that reveals fundamental character flaws? The whole ritual of preparing for a first date feels like getting ready for a job interview where the position requirements are mysterious and the interviewer might be completely insane.

At exactly seven o’clock—and I mean exactly, because I was watching the clock on my phone like it held the secrets of the universe—my doorbell rang with the kind of punctuality that suggested either excellent time management skills or an obsessive personality that would eventually drive me crazy.

Chapter 2: The Perfect Gentleman

I took a deep breath, grabbed my purse, checked my reflection one more time in the hallway mirror, and opened the door to find Andy holding a small bouquet of wildflowers wrapped in brown paper with what appeared to be a hand-tied ribbon.

He was tall—probably around six-foot-two—with dark brown hair that looked like he’d spent some time styling it but not so much that it seemed vain. He was wearing a button-down shirt that looked freshly pressed, dark jeans that actually fit properly, and shoes that had clearly been polished recently. His smile was so earnest and genuine that it almost made me forget about Kevin and his extensive collection of vintage soup spoons, each with its own detailed provenance story.

“Hi, Sarah,” he said, and his voice was warm and confident without being presumptuous. “I didn’t know what your favorite flowers were, but I saw these at the farmer’s market this morning and thought they looked pretty. I hope you like them.”

“They’re absolutely perfect,” I said, accepting the bouquet and immediately feeling some of my pre-date anxiety begin to evaporate. “Thank you so much. That was really thoughtful.”

And you know what? He waited patiently while I found a vase in my kitchen cabinet, filled it with water, and arranged the flowers on my dining table. No checking his phone every thirty seconds, no tapping his foot impatiently, no subtle sighs of frustration or glances at his watch. He just stood there, looking around my apartment with what seemed like genuine interest, occasionally commenting on my book collection or the photographs I had hanging on the walls.

“You have really good taste,” he said, pausing in front of a framed print I’d bought at a local art fair. “I love how you’ve decorated this place. It feels warm and lived-in.”

“Thank you,” I replied, surprised by how much his approval meant to me. “I’ve been here for about three years now, so I’ve had time to make it feel like home.”

“Ready?” he asked once I’d finished with the flowers, and then—get this—he opened the car door for me.

I know, I know, it sounds old-fashioned and maybe even a little antiquated in our modern world of gender equality and independent women who can certainly open their own doors. But when’s the last time someone actually did that for you? Not as a political statement or a performance of traditional gender roles, but just as a small act of courtesy that made you feel cared for? I was genuinely surprised by how much I appreciated the gesture.

His car was clean but not obsessively so—no air fresheners hanging from the rearview mirror, no collection of parking garage tickets stuffed into the cup holders, no mysterious stains on the upholstery that would make me question his personal hygiene. The radio was tuned to a classic rock station at a reasonable volume, and he asked if I minded the music before pulling away from the curb.

Dinner was even better than I’d expected, which honestly says more about my lowered expectations than about the quality of the restaurant. He’d chosen a small Italian place downtown that I’d never been to but had always wanted to try—the kind of neighborhood spot with mismatched chairs and handwritten specials on a chalkboard that suggested the owners cared more about the food than about impressing people with fancy décor.

Andy held doors, pulled out my chair, and asked about my job in graphic design like he actually cared about the answer rather than just waiting for his turn to talk about himself. When I told him about the logo project I was working on for a local nonprofit, he asked thoughtful follow-up questions about the creative process and the challenges of visual communication.

“I always admire people who do what they love for a living,” he said, cutting into his chicken parmesan with the kind of precise movements that suggested good table manners without being fussy about it. “Not everyone has the guts to pursue a creative career. It takes real courage to make art your profession.”

And when I complimented the restaurant’s atmosphere and mentioned how much I was enjoying the food, he said, “Right? But I think our waiter deserves the real five stars. Have you noticed how he’s been anticipating what we need without being intrusive? That’s real skill.”

I found myself softening toward him in a way that frankly terrified me, because I’d been hurt enough times to know that the men who seem too good to be true usually are. But there was something about Andy’s attention to detail, his consideration for other people, his apparent lack of ego or hidden agenda that made me want to believe that maybe this time would be different.

You know how it is when you’re dating: you start to think maybe this guy won’t have some weird deal-breaker hiding in his back pocket. Maybe he won’t turn out to collect something strange or have strong opinions about conspiracy theories or reveal that he’s never read a book since high school. Maybe, just maybe, this will be the person who restores your faith in the possibility of finding someone who’s both attractive and sane.

Spoiler alert: those guys always have a deal-breaker. Always. It’s just a matter of time before they reveal whatever particular brand of crazy they’ve been hiding behind their charming exterior.

The conversation flowed easily throughout dinner. He told me about his work as an accountant—which sounds boring but was actually quite interesting when he described the problem-solving aspects and the satisfaction of helping small businesses manage their finances more effectively. I shared stories about my most challenging design projects and the satisfaction of seeing a client’s vision come to life through visual communication.

We discovered that we both loved hiking, though he was more of a mountain trail person while I preferred coastal walks. We both read voraciously, though his tastes ran more toward non-fiction while I was addicted to literary fiction and the occasional romance novel that I would never admit to enjoying. We both had complicated relationships with social media and were trying to spend less time scrolling mindlessly through our phones.

When he talked about his family, there was genuine warmth in his voice. When he asked about mine, he listened to my answers with what seemed like real interest. When the couple at the table next to us got into a quiet argument about something, he discreetly suggested we give them some privacy by focusing on our own conversation rather than obviously eavesdropping like some people do.

By the time we’d finished our entrees and were debating whether to order dessert, I was feeling something I hadn’t experienced in months: optimistic about the possibility of a second date. Maybe even a third. Maybe, if I was really lucky, this could be the beginning of something real and lasting and healthy.

Chapter 3: The Red Flag I Ignored

When the check arrived, delivered by our attentive waiter with a smile and a subtle bow, I instinctively reached for my phone to call an Uber. This wasn’t about feminism or making a statement about gender roles—it was about safety and maintaining the boundaries I’d established after several uncomfortable situations where first dates had ended with awkward front-door negotiations and unwanted assumptions about what dinner might have earned them.

I have a rule, you see, developed through experience and reinforced by countless stories from friends who’d learned similar lessons the hard way: no rides home on first dates. It’s just safer that way and avoids any misunderstandings at the front door about what level of intimacy might be expected in exchange for a meal and some pleasant conversation.

Andy looked genuinely surprised when he saw me opening the Uber app on my phone. “What are you doing?” he asked, his brow furrowing in what appeared to be confusion rather than offense.

“Just calling a ride home,” I said, trying to keep my tone casual and matter-of-fact. “Thanks for dinner, by the way. I had a really wonderful time.”

“No way,” he said, reaching across the table to gently touch my hand in a gesture that was somehow both protective and presumptuous. “A gentleman drives his date home and makes sure she gets inside safely. That’s just basic courtesy.”

Now, I should have stuck to my rule. I really should have, because rules like that exist for good reasons and are usually based on accumulated wisdom from previous mistakes. But Andy looked so sincere when he said it, and that smile was back—the one that had been charming me all evening, the one that made me forget about all my carefully constructed dating boundaries and the hard-learned lessons that had inspired them.

There was something in his tone that suggested he was genuinely concerned about my safety rather than looking for an opportunity to extend the evening or angling for an invitation inside my apartment. He seemed almost offended by the idea that I would take a ride-share service when he was perfectly capable of ensuring I got home safely.

“I always drive my dates home,” he continued, his voice taking on the kind of earnest quality that suggested this was a matter of personal principle rather than convenience. “It’s the right thing to do. Besides, I want to make sure you get inside okay. You never know what kind of weirdos are out there.”

So I caved. Sue me. I let him pay for dinner, accepted his offer to drive me home, and told myself that my safety rule was probably overly cautious anyway. After all, he’d been nothing but respectful all evening, and Marcus had vouched for him, and sometimes you have to take reasonable risks if you want to build meaningful connections with other human beings.

The drive to my apartment took about twenty minutes through the relatively quiet Saturday evening streets of our mid-sized city. Andy kept the conversation light and easy, asking about my neighborhood and commenting on the beautiful old trees that lined my street. He didn’t try to extend the evening by suggesting we stop somewhere for coffee or drinks, didn’t ask intrusive questions about my living situation, didn’t make any comments that felt like attempts to invite himself inside.

He opened the car door for me again when we arrived at my building, walked me to the entrance, and waited while I fumbled with my keys in that awkward way that happens when you’re being watched and trying to appear more competent than you feel.

“Thank you for a lovely evening,” he said, making no move to come closer or follow me inside. “I hope we can do this again soon.”

“I’d like that,” I replied, and I meant it. “Thank you for dinner and for the ride home. That was really thoughtful.”

When I turned to wave from my living room window, he waved back before pulling away from the curb and disappearing into the night. I watched his taillights until they turned the corner, feeling that warm glow of satisfaction that comes from an evening that exceeded all reasonable expectations.

I went to bed that night feeling something I hadn’t felt in months: genuinely hopeful about the possibility of finding love. Maybe even lucky to have met someone who seemed to understand that treating a woman well didn’t require elaborate gestures or expensive gifts, just consistent consideration and basic human decency. Can you believe that? I actually thought I might have found one of the good ones.

I lay in bed replaying the best moments of the evening—his laugh when I told him about my disastrous attempt to make homemade pasta the previous weekend, the way he’d listened when I talked about my work, the genuine interest he’d shown in my opinions about everything from local politics to the best hiking trails in the area.

For the first time in months, I fell asleep without scrolling through dating apps or wondering what was wrong with me that I couldn’t seem to connect with anyone who wasn’t either boring or crazy or both. Instead, I drifted off thinking about second date possibilities and maybe, just maybe, the beginning of something real.

Chapter 4: The Morning After Shock

The next morning, Sunday, I woke up naturally around eight o’clock feeling more rested and optimistic than I had in weeks. I made coffee, checked my email, and was just settling down with the Sunday crossword puzzle when my phone buzzed at exactly 7:13 AM with a notification that made me blink hard and check the screen twice, convinced I was still dreaming or suffering from some kind of caffeine-withdrawal hallucination.

A PayPal request. At first, I thought it was spam—you know how those scammers work, sending random payment requests hoping that busy people will accidentally approve them without looking carefully at the details. But when I opened the notification and saw Andy’s name attached to an itemized list of expenses, my brain just stopped working for a moment.

Are you ready for this? Because I’m not sure I was, even after staring at my phone screen for what felt like several minutes but was probably only thirty seconds.

He’d sent me a bill. An actual, itemized bill for the previous evening’s activities.

The breakdown read like something a rideshare company might send, except instead of being a legitimate business expense, it was apparently Andy’s calculation of what I owed him for the basic courtesy of driving me home after a date he had initiated and enjoyed as much as I had.

Gas from restaurant to my place: $4.75 Car depreciation (calculated mileage): $3.50 Downtown parking during dinner: $20.00 Cleaning fee for “puddle splash marks on passenger side”: $9.00 Total amount due: $37.25

I stared at my phone for a full thirty seconds, trying to process what I was seeing and wondering if this was some kind of elaborate joke that I wasn’t sophisticated enough to understand. Was this Andy’s idea of humor? Was he testing my reaction to see if I was the kind of woman who could appreciate creative comedy? Was this some new dating trend I hadn’t heard about, like splitting checks but for transportation costs?

But no, the PayPal request was completely serious, complete with a professional-looking note that read: “Thank you for a wonderful evening! Please find attached the expenses for your safe transport home. Looking forward to our next date! – Andy”

Then I started laughing. Not just chuckling or smiling, but full-on, doubled-over, tears-streaming-down-my-face laughter that echoed through my apartment and probably concerned my neighbors. I laughed so hard I nearly dropped my coffee mug and had to sit down on my couch to avoid falling over.

This man, who had seemed so perfect just twelve hours earlier, had actually itemized the cost of basic human decency and sent me a bill for it like I was a customer who had hired his services rather than a woman he’d taken on a date. Can you even imagine the thought process that led to this decision?

Picture this: Andy, sitting in his probably very organized apartment with his accounting spreadsheets and calculator, carefully documenting every expense related to our evening together, assigning monetary value to gestures that most people would consider part of the basic social contract of dating. Did he keep receipts? Did he measure the exact distance from the restaurant to my apartment to calculate the depreciation costs? Did he actually photograph the alleged puddle splash marks on his passenger side door?

The cleaning fee was particularly impressive in its audacity. When exactly had these puddle splash marks occurred? I certainly hadn’t noticed any puddles during our walk from the restaurant to his car. Had he inspected his vehicle after dropping me off and discovered mysterious stains that he attributed to my presence? Was this a standard charge he applied to all passengers, or had I somehow been particularly destructive during the twenty-minute drive to my apartment?

I started laughing again every time I looked at the itemized list. The precision of it was almost admirable in its complete tone-deafness. $4.75 for gas—not $5, but exactly $4.75, calculated presumably with mathematical precision based on current fuel prices and the exact mileage between the restaurant and my apartment. $3.50 for car depreciation, which suggested he had some kind of formula for calculating the reduced value of his vehicle based on passenger miles.

But it was the $20 parking fee that really got me. We had eaten at a restaurant in the downtown area where street parking was free after six PM on weekends. I had specifically noticed this when we arrived because I had been prepared to offer to split the parking costs if necessary. Unless Andy had chosen to park in some premium location that I hadn’t been aware of, that $20 fee was either completely fictional or represented his estimate of what his parking time was worth.

Chapter 5: The Perfect Response

After I finished laughing myself into a state of breathless hysteria, I decided that Andy’s entrepreneurial approach to dating expenses deserved an equally creative response. If he was going to treat our romantic evening like a business transaction, then I was going to show him how customer service really worked.

I opened my own PayPal account and sent him $50 with a note that I spent considerable time crafting to achieve the perfect balance of sarcasm and apparent sincerity: “Thank you for itemizing your gentleman services! Here’s $37.25 for your listed expenses plus a $12.75 tip for door opening, chair pulling, and overall chivalrous behavior. Please rate your customer experience five stars! Looking forward to never seeing you again! – Sarah”

Then I immediately blocked his number without a second thought, because any man who would send his date a bill for the privilege of his company was not someone I needed to maintain contact with, regardless of how charming he had seemed during dinner.

But I wasn’t done with this situation, oh no. I was just getting started, because this story was too good to keep to myself, and Andy’s behavior was too outrageous to let pass without some form of social consequences.

I immediately texted my brother: “UPDATE: Mystery solved about why your pickleball friend Andy is still single!” followed by screenshots of both Andy’s itemized invoice and my sarcastic payment response.

Then I spent the rest of the morning on my couch, periodically bursting into fresh waves of laughter every time I thought about different aspects of Andy’s bill. The more I considered it, the funnier it became. Had he planned this from the beginning? Was sending post-date invoices his standard operating procedure? Did he have a whole filing system for tracking dating-related expenses?

I started imagining Andy’s apartment filled with spreadsheets documenting every social interaction: “Lunch with coworkers: $12.50 for my share of appetizers, $3.25 for extra napkins used by colleagues.” “Family dinner: $8.75 for gas to parents’ house, $2.00 for wear and tear on dress shoes, $15.00 for emotional labor of listening to Mom’s stories.”

Around noon, just as I was starting to wonder if I should frame Andy’s invoice as a conversation piece for my apartment, Marcus called with the kind of shocked amusement in his voice that suggested he had been processing my screenshots for the past hour.

“Sarah, I am so, so sorry,” he said before I could even say hello. “I had absolutely no idea he was like this. None of us did.”

“How could you have known?” I replied, still giggling intermittently. “I’m betting Andy saves his special entrepreneurial charm for romantic encounters. I doubt he sends his pickleball buddies bills for sharing court time.”

“Actually,” Marcus said, and I could hear the storyteller tone creeping into his voice that meant he had really good gossip to share, “there’s more to this story. Andy was at pickleball this morning, bragging to all the guys about your date last night. He was telling everyone it was ‘like something out of a romantic comedy’ and that he was ‘pretty sure he’d found his future wife.'”

I snorted so loudly I’m surprised Marcus didn’t ask if I was choking. “Oh, it was definitely movie-worthy. Just not the genre he was thinking of. More like a horror-comedy hybrid.”

“Yeah, well, when I showed the guys your screenshots, the entire group went dead silent for about thirty seconds. Then Andy muttered something I’ll never forget as long as I live: ‘Well, chivalry doesn’t pay for itself, you know.'”

“He did not say that.”

“He absolutely did. Word for word. And then, when the guys started asking him what the hell he was thinking, he tried to defend himself by saying that modern women should appreciate transparency in dating expenses and that he was just being honest about the real costs of courtship.”

I was laughing again, the kind of helpless laughter that makes your sides hurt and your eyes water. “Please tell me you’re joking. Please tell me he didn’t actually use the phrase ‘real costs of courtship’ with a straight face.”

“I wish I was making this up, but Andy was completely serious. He started explaining his dating philosophy, which apparently involves treating romantic relationships like business partnerships where all expenses should be shared equally. He said he’d been absorbing the costs of dating for years and had finally decided to implement a more equitable system.”

“An equitable system,” I repeated, still giggling. “He turned dating into a fee-for-service business model.”

“It gets better,” Marcus continued. “When one of the guys asked him if he planned to charge all his future dates for transportation, Andy said he was considering implementing a comprehensive dating fee structure that would include charges for restaurant recommendations, conversation quality, and what he called ’emotional labor overhead.'”

“Stop,” I gasped, laughing so hard I could barely speak. “You’re going to make me pass out.”

“The best part was when someone asked him if he expected women to tip based on date satisfaction, and Andy got this thoughtful look on his face like he was seriously considering adding a gratuity option to his invoicing system.”

Needless to say, the Saturday morning pickleball group had voted Andy out. Unanimously. Within fifteen minutes of seeing my screenshots and hearing his defense of the billing system, the guys had decided that Andy’s membership in their social circle was no longer welcome.

“I mean, we all knew he was a little uptight about money,” Marcus explained, “but none of us realized he was completely insane about it. Who sends their date a bill? Who thinks that’s acceptable human behavior?”

I had to admit that felt pretty satisfying. Not because I wanted Andy to lose his friends, but because it was validating to know that his behavior was as outrageous as I’d thought and that other people found it equally unacceptable.

Chapter 6: Going Viral

But here’s where the story gets really interesting, and where I learned that Andy’s accounting approach to romance was apparently more widespread than any of us had realized.

Fast-forward to the following weekend. I was doing my usual Saturday morning routine: sprawled on my couch in my most comfortable pajamas, coffee within easy reach, scrolling through TikTok with the dedication of someone who had nowhere else to be and no responsibilities more pressing than deciding whether to order groceries online or venture into the real world.

Suddenly, I choked on my coffee and nearly dropped my phone when a video appeared on my feed that made me question whether I was experiencing some kind of déjà vu or if the universe had decided to play an elaborate practical joke on me.

There, on my screen, was a young woman who looked like she was probably in her early twenties, sharing screenshots of what she called an “itemized date invoice” from a guy she identified as Andy from her local area.

The amounts were slightly different from what I’d received, but the audacious entitlement was exactly the same. Gas expenses, car depreciation calculated to the penny, parking fees, and—this was new—a line item for “cologne and grooming preparation: $15.00” that suggested Andy had been refining his billing system based on customer feedback.

“This guy really thinks he’s Uber with dinner service,” the girl said in the video, holding up her phone to show Andy’s PayPal request. “He charged me for the privilege of sitting in his car and breathing his air. I’m pretty sure this violates several dating conventions and possibly some consumer protection laws.”

I couldn’t believe what I was seeing. Andy had done this before. This wasn’t some weird one-off moment of poor judgment triggered by our specific date or some kind of accounting brain malfunction brought on by tax season stress. No, this was Andy’s actual dating strategy, his systematic approach to romantic relationships that apparently involved turning every social interaction into a billable consulting session.

The comments section was absolutely brutal, and I lived for every single savage response:

“Ladies, beware of Andy’s Taxi & Misogyny Service – now with surcharges for emotional labor!”

“At least Uber drivers offer mints and phone chargers. This guy just offers audacity.”

“This man really said, ‘Pay me back for being a gentleman.’ Sir, that’s not how chivalry works.”

“Plot twist: He’s actually charging interest on all these invoices and building a dating empire.”

“Next he’ll be asking for a security deposit before dinner.”

I immediately sent the video to Marcus with a simple message: “Your former pickleball friend is TikTok famous, and not in a good way.”

His response was immediate and mortified: “I’m never trusting my judgment about men ever again. Also, I’m changing pickleball groups.”

I spent the rest of the afternoon reading comments and sharing the video with friends, which turned into this massive group chat about dating horror stories that went on for hours. It was like opening the floodgates on years of accumulated frustration with men who had revealed themselves to be completely unsuitable for human relationships through various forms of shocking behavior.

My friend Jessica shared a story about a guy who had charged her for the gas he used driving to pick her up for a date, then complained when she didn’t reimburse him for his time spent getting ready. My friend Lauren told us about a man who had calculated the exact cost of the drinks he’d bought her and then deducted that amount from what he paid her when she did freelance work for his company.

It turned into this therapeutic sharing session about all the ways that certain men reveal their true characters through their attitudes toward money, courtesy, and basic human decency. And honestly? It was incredibly validating to realize that Andy’s behavior was part of a larger pattern of entitled ridiculousness that women all over the world were dealing with.

The TikTok video ended up getting over two million views and spawning dozens of response videos from other women sharing their own experiences with men who had similarly commodified dating and romance. There were stories about guys who charged for parking, calculated restaurant tip percentages down to the penny and expected reimbursement for their half, and even one memorable tale about a man who had created a spreadsheet tracking the cost of every text message he sent.

Chapter 7: The Broader Pattern

What fascinated me most about the viral response to Andy’s invoicing system was how it revealed a much larger conversation about dating, gender roles, and the entitlement that some men feel toward women’s time, attention, and gratitude.

The comments on the TikTok video weren’t just making fun of Andy’s specific brand of romantic entrepreneurship—they were unpacking the underlying assumption that women owe men something in exchange for basic courtesy, that chivalry is a service that should be compensated rather than a simple expression of mutual respect.

“This is what happens when men think treating women like human beings is a favor they’re doing instead of basic decency,” one commenter wrote.

“He’s literally charging her for the honor of his presence. The audacity is breathtaking,” wrote another.

“Imagine being so entitled that you think opening a car door creates a debt that needs to be settled via PayPal,” added a third.

The conversation expanded beyond Andy’s specific invoice to include broader discussions about men who kept detailed mental tallies of everything they did for women, who expected gratitude and reciprocation for gestures that should have been automatic expressions of consideration.

Women shared stories about dates who had calculated exact splits for dinner checks down to individual appetizer bites, men who had complained about the cost of flowers or movie tickets as if these were unexpected business expenses rather than choices they had made freely, guys who had treated every act of courtesy like an investment that should generate returns.

What struck me most was how many women had experienced some version of Andy’s behavior—maybe not itemized invoices, but definitely the sense that certain men viewed dating as a transactional relationship where women were expected to provide compensation (emotional, physical, or financial) for male attention and effort.

I started thinking about all the times I’d felt pressured to show excessive gratitude for basic politeness, to downplay my own preferences to avoid seeming high-maintenance, to accept behavior that made me uncomfortable because a man had spent money on dinner or driven me somewhere or performed some other gesture that was supposedly generous but felt more like an obligation being created.

The viral response to Andy’s invoice story became a catalyst for thousands of women to examine their own dating experiences and recognize patterns of entitlement and manipulation that they’d previously accepted as normal or inevitable.

“I just realized my ex used to keep track of every nice thing he did for me and bring it up during arguments,” one woman commented. “He treated kindness like a credit system where I owed him points.”

“My last boyfriend calculated how much money he spent on our relationship and expected me to pay him back when we broke up,” shared another.

“I went on a date with a guy who complained about parking costs the entire evening and then suggested I Venmo him for half. The restaurant had free valet,” wrote a third.

The more I read, the more I realized that Andy’s invoice wasn’t just a funny story—it was a perfect crystallization of an attitude that many women had encountered in various forms throughout their dating lives.

Chapter 8: The Lessons Learned

Looking back on the whole Andy experience now, several months later, I’m actually grateful it happened. Not because I enjoyed being charged for the privilege of his company, but because it taught me several valuable lessons about dating, boundaries, and trusting my instincts.

First, I learned that my safety rule about taking my own transportation on first dates exists for good reasons that go beyond just physical safety. When someone insists on driving you home, they’re not just offering courtesy—they’re creating a situation where you become dependent on them, where you owe them something, where the power dynamic shifts in their favor.

Andy’s insistence on driving me home wasn’t really about ensuring my safety, as I’d initially believed. It was about creating an opportunity to later claim that he’d provided a service that deserved compensation. If I’d stuck to my original plan and taken an Uber, he wouldn’t have had grounds for his ridiculous invoice, and I would have avoided the entire situation.

The experience taught me to trust that little voice in my head that whispers warnings when something feels off, even if I can’t immediately articulate why. When Andy insisted on driving me home, some part of me felt uneasy about it, but I ignored that instinct because his reasoning seemed logical and his intentions appeared good. Now I know that feelings of unease often pick up on subtle signals that our conscious minds haven’t processed yet.

Second, I learned that truly generous people don’t keep score. When someone genuinely wants to do something nice for you, they don’t track their efforts or expect specific returns on their investment. They certainly don’t send you a bill afterward itemizing the costs of their kindness.

Andy’s invoice revealed that every gesture during our date—opening doors, pulling out chairs, driving me home—had been calculated performances rather than authentic expressions of consideration. He hadn’t been treating me well because he cared about my comfort or happiness; he’d been accumulating billable hours that he planned to cash in later.

This realization helped me understand the difference between genuine courtesy and performative chivalry. Real kindness is freely given without expectation of reward. Performative kindness always comes with strings attached, even if those strings aren’t immediately visible.

Third, I learned that how someone responds to rejection or disappointment tells you everything you need to know about their character. When Andy realized that I wasn’t going to be impressed by his entrepreneurial approach to dating expenses, when he discovered that other people found his behavior unacceptable, his response was to double down on his entitlement rather than reflect on his actions.

A person with genuine integrity would have been mortified by the realization that they’d hurt or offended someone. They would have apologized, learned from the experience, and changed their behavior. Andy, instead, defended his invoice system and started refining it for future use. That told me everything I needed to know about his capacity for empathy and growth.

The experience also taught me about the power of sharing stories and refusing to suffer in silence. By telling Marcus about Andy’s invoice, by sharing screenshots with friends, by participating in the broader conversation that erupted on social media, I helped create a space where other women could recognize similar patterns in their own experiences and feel validated in their reactions to unacceptable behavior.

Sometimes we doubt our own responses to situations that feel wrong but that others might dismiss as harmless or normal. Andy’s invoice felt outrageous to me, but part of me wondered if I was overreacting, if this was some new dating trend I didn’t understand, if I was being unreasonable in my shock and offense.

The viral response to the TikTok video confirmed that my reaction was not only appropriate but shared by millions of other people who recognized Andy’s behavior as entitled, manipulative, and completely unacceptable. That validation was incredibly powerful and reinforced my trust in my own judgment about what I will and won’t tolerate in relationships.

Chapter 9: Moving Forward

I’m still dating, though with a much clearer understanding of my own boundaries and a much lower tolerance for red flags disguised as romantic gestures. I’m still single, still occasionally rolling my eyes at my brother’s well-meaning but often misguided suggestions about men from his various sports leagues and social circles.

But now I always take my own ride home from first dates, and I do it with a smile, knowing that any man worth keeping around won’t send me a bill for his efforts to get to know me. I’ve learned to listen to my instincts, to trust my initial reactions to people’s behavior, and to recognize that genuine kindness doesn’t come with hidden fees or expectations of reciprocation.

Marcus, for his part, has become much more cautious about his matchmaking attempts. The Andy experience taught him that surface-level interactions with people don’t necessarily reveal their true character, and that vouching for someone’s romantic suitability requires deeper knowledge than can be gained from weekend pickleball games.

“I think I’ll stick to making work friends and leave the dating recommendations to the professionals,” he told me recently. “Clearly, my judgment about men’s fitness for romance is questionable at best.”

The Andy story has become legendary in our friend group, brought out at dinner parties and gatherings whenever someone needs a reminder that dating horror stories can always get worse, or whenever someone needs encouragement to trust their instincts about questionable behavior from potential romantic partners.

But more than just entertainment value, the story serves as a cautionary tale about the importance of maintaining boundaries, recognizing red flags, and understanding that someone’s treatment of you reveals their character more clearly than their words or apparent charm.

Epilogue: The Gift of Clarity

Six months after the invoice incident, I received an unexpected message through the TikTok app from the young woman whose video had gone viral. She wanted to thank me for sharing my story with Marcus’s pickleball group, because it had given her the courage to share her own experience and had ultimately led to Andy being exposed as a serial dating entrepreneur.

“I thought I was the only one,” she wrote. “I thought maybe there was something wrong with me for being offended by his bill. Seeing that he’d done it to other women helped me realize that this was a pattern of behavior, not a one-time mistake or a joke that I didn’t understand.”

She went on to tell me that several other women had contacted her after seeing her video, sharing their own stories about Andy’s invoicing system and revealing that his dating expenses billing had been going on for over a year. Apparently, he’d been refining his system based on customer feedback, adding new line items and adjusting his rates based on market research.

“The cologne and grooming fee was new,” she explained. “I guess he decided that his preparation time should be billable at consulting rates.”

The revelation that Andy had been systematically billing women for dating expenses for over a year was both horrifying and oddly satisfying. It confirmed that leaving him was absolutely the right decision, and it provided closure that his behavior hadn’t been triggered by something specific about me or our interaction.

More importantly, it reinforced the lesson that sharing our stories about unacceptable behavior can protect other people from similar experiences. If I hadn’t told Marcus about the invoice, if the TikTok video hadn’t gone viral, if women hadn’t started commenting about their own experiences with entitled men, Andy might have continued his romantic entrepreneurship indefinitely.

Instead, his behavior was exposed, his social circle was informed, and his future dating prospects were significantly diminished by his well-deserved reputation as the guy who charges women for the privilege of his company.

The Andy experience taught me that the worst dates often make the best stories, but more importantly, they make the best lessons about what we will and won’t accept from people who want to be part of our lives. Sometimes you have to encounter someone completely unacceptable to clarify what acceptable actually looks like.

I’m still open to love, still hopeful about finding someone who understands that genuine affection can’t be commodified, that real courtesy doesn’t come with a price tag, and that the best relationships are built on mutual respect rather than transactional exchanges.

But I’m also perfectly content being single until I find someone who treats kindness as a natural expression of their character rather than a billable service that requires compensation. Because thanks to Andy, I now know the difference, and I’ll never settle for less than I deserve again.

The flowers Andy brought me that first night lasted about a week before they wilted and had to be thrown away. But the lesson he taught me about trusting my instincts, maintaining my boundaries, and recognizing genuine character—that lesson will last forever.

And honestly? That’s worth way more than $37.25.

The End

This story reminds us to trust our instincts, maintain our boundaries, and recognize that genuine kindness doesn’t come with hidden fees or expectations. It teaches us that how someone treats us when they think we owe them something reveals their true character, and that the worst dating experiences often provide the clearest lessons about what we deserve in relationships. Most importantly, it shows us that sharing our stories about unacceptable behavior can protect others and help create a culture where entitled, manipulative conduct is recognized and rejected rather than tolerated or excused.