The Expensive Mistake: My Date Insisted on Driving Me Home—I Still Regret Saying Yes

Part 1: The Fraternal Fix-Up

When her brother tried to set her up with a seemingly perfect guy, she had her reservations but agreed to give it a shot. His flowers, smooth demeanor, and charming smile almost convinced her he was the real deal. But when he insisted on driving her home, a quiet voice inside warned her: Don’t do it. A warning she would later regret ignoring.

You know that line, “I’ve got the ideal man for you”? Well, that’s exactly how this entire mess began, and trust me, it’s a saga that only gets more unbelievable with every detail I recall.

My brother, Marcus, had been relentlessly promoting this guy named Andy from his Saturday morning pickleball league for what felt like an eternity, but was probably only about three weeks. Marcus is the type who latches onto an idea and pushes it with the relentless drive of a motivated drill sergeant until everyone caves or changes their phone number.

“Seriously, he’s not just some guy, Sarah,” Marcus insisted for what had to be the sixteenth time, pouring himself a refill of his protein shake at my kitchen counter. This was happening on a peaceful Tuesday night I’d planned to spend in solitude with Netflix and my leftover lo mein. “This Andy is courteous, smart, works in accounting, owns a reliable car and his own place, and get this—he’s still unattached. Too long, if you ask me, which should tell you how high his standards are.”

I rolled my eyes so dramatically I feared they might pop out and join the conversation on their own. “That’s precisely what you said about Kevin six months ago, remember? The antique spoon aficionado who didn’t just collect them, but who had a profoundly unsettling emotional bond with old silverware?”

“Okay, Kevin was a misjudgment, I’ll grant you that,” Marcus conceded, raising his hands in a gesture of surrender. “But Andy is different. There’s just something… solid about him. Reliable. The kind of person Mom would adore and Dad might actually approve of.”

There was a sincerity in his voice that made me pause mid-chop. I was aggressively dicing some innocent carrots for a stir-fry, channeling all my pent-up dating frustration into the root vegetables, much like any rational twenty-eight-year-old would after a string of dates that left me doubting the very existence of decent, non-mythical men.

Marcus wasn’t usually this persistent about his attempts at matchmaking. Normally, he’d suggest someone, I’d politely decline, and we’d immediately transition to more normal sibling topics, like who was visiting our folks next or if his new workout routine was actually effective or just making him insufferable. But this Andy person had captured his complete attention in a way that was simultaneously touching and slightly alarming.

“Look,” Marcus continued, placing his protein shake down and leaning against my counter with the earnest intensity he perfected on his high school debate team, “I know your luck has been rough lately. We both know Kevin was a disaster from the second he started explaining his spoon grading rubric. But I genuinely believe Andy could be the exception. He’s been asking about you since I mentioned I had a successful, single sister.”

Here’s the thing about brothers: they won’t quit when they think they’re being helpful, even when their help feels more like light torture. Honestly, I was done with “nice guys” who came with an unexpected, strange expiration date—men who seemed totally normal until they unveiled a secret obsession with miniature trains, a need for all food to be beige, or a passionate conviction that women should split every cost down to the last penny while simultaneously expecting men to hold every door.

Yet, something about Marcus’s tone—the way he looked so genuinely invested and hopeful in this potential match—slowly wore down my defenses like water smoothing a rough stone. Perhaps it was the forty-minute drive he’d made just to have this conversation in person instead of sending a quick text. Maybe it was the enthusiasm he spoke of Andy with, an enthusiasm he usually reserved for his fantasy football draft. Or perhaps I was simply tired of being the perpetually single woman at family gatherings, fielding increasingly desperate but well-meaning questions about my love life from relatives who seemed to view being unmarried at twenty-eight as a personal flaw requiring urgent intervention.

“Fine,” I finally relented, putting my knife down and facing him with an expression I hoped conveyed resigned acceptance rather than total defeat. “One date. That’s it. And if this turns into another Kevin saga, I am permanently retiring you from matchmaking. No more suggestions, no more helpful hints about guys from your leagues, no more casual mentions of single colleagues. Deal?”

Marcus’s face instantly brightened as if I’d just agreed to an organ donation. “Deal! You are going to love him, Sarah. I truly believe this is the one.”

Famous last words, right? I should have known right then that any phrase starting with “you’re going to love him” was essentially a prophecy of romantic catastrophe. But I was committed to being open-minded, ready to give romance a chance, trying to prove to myself and everyone else that I wasn’t impossibly picky, emotionally unavailable, or whatever other labels people applied to my single status.

So there I was the following Saturday night, standing in front of my bedroom mirror at six forty-five, adjusting my dress for what had to be the fifteenth time in an hour. I’d picked a straightforward navy blue dress—nice enough to show effort but not so extravagant as to hint at unreasonable expectations for the evening.

Why do we put ourselves through this? What is the point of trying to look flawless for a stranger who might turn out to secretly collect belly button lint, have rigid opinions on dishwasher loading, or believe that pineapple on pizza is a sign of moral decay? The entire pre-date ritual feels like preparing for a job interview where the required skills are a total mystery, and the hiring manager might be clinically unstable.

At precisely seven o’clock—and I mean exactly, as I was watching my phone clock like it held the secrets of the universe—my doorbell rang with a level of punctuality that suggested either impressive time management or an obsessive personality that would eventually drive me insane.

Part 2: The Ideal Date

I took a calming breath, grabbed my clutch, checked my reflection one final time in the hallway mirror, and opened the door to find Andy holding a modest bouquet of wildflowers, neatly wrapped in brown paper and tied with a simple ribbon.

He was tall—maybe six-two—with dark brown hair that looked styled but not vain. He wore a crisp, button-down shirt, dark jeans that fit perfectly, and freshly polished shoes. His smile was so warm and genuine it almost made me forget about Kevin and his exhaustive, detailed histories for every vintage soup spoon he owned.

“Hi, Sarah,” he said. His voice was confident and friendly without being overly familiar. “I didn’t know your favorite flowers, but I saw these at the market this morning and thought they looked lovely. I hope you like them.”

“They’re absolutely perfect,” I replied, accepting the bouquet and instantly feeling some of my pre-date nerves disappear. “Thank you so much. That was incredibly thoughtful.”

And you know what? He waited patiently while I found a vase, filled it with water, and arranged the flowers on my dining table. No checking his phone constantly, no anxious foot-tapping, no subtle sighs of boredom or glances at his watch. He just stood there, observing my apartment with what seemed like real curiosity, occasionally commenting on my extensive book collection or the photos on my walls.

“You have excellent taste,” he commented, pausing in front of a framed print I’d bought at an art fair. “I love how you’ve decorated this space. It feels cozy and lived-in.”

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

“Ready?” he asked once I was done with the flowers, and then—believe this—he opened the car door for me.

I know, I know, it sounds a bit outdated, maybe even archaic in our modern era of independence and gender equality where women can certainly manage their own doors. But when was the last time someone actually did that for you? Not as some grand statement, but simply as a small, genuine act of courtesy that made you feel appreciated? I was truly taken aback by how much I liked the gesture.

His car was tidy, but not obsessively so—no dangling air fresheners, no pile of parking stubs in the cup holders, no strange stains on the seats that would make me doubt his hygiene. The radio was tuned to classic rock at a moderate volume, and he checked if I minded the music before driving away from the curb.

Dinner was even better than I’d hoped, which honestly speaks volumes about my historically low dating expectations rather than the caliber of the restaurant. He had chosen a small, downtown Italian spot I’d always wanted to visit but hadn’t—the kind of local haunt with mismatched furniture and specials scrawled on a chalkboard, suggesting the owners prioritized the food over impressing patrons with décor.

Andy continued to hold doors, pull out my chair, and ask about my work in graphic design as if he truly cared about the answer, rather than just waiting for his opportunity to talk about himself. When I described the logo project I was working on for a local non-profit, he asked perceptive follow-up questions about the creative process and the difficulties of visual communication.

“I’ve always admired people who are passionate about their career,” he said, slicing into his chicken parmesan with the careful precision of someone with good, unfussy table manners. “Not everyone has the nerve to pursue a creative path. It requires genuine courage to make art your livelihood.”

And when I complimented the restaurant’s vibe and mentioned how good the meal was, he replied, “Right? But I think our waiter is the real star here. Have you noticed how he’s anticipated everything we need without hovering? That’s a real talent.”

I started to feel a profound softening toward him, which frankly terrified me. I’d been hurt enough times to know that men who seem too perfect usually are. But there was something about Andy’s consideration for others, his attention to detail, and his apparent lack of a hidden agenda or ego that made me want to believe that perhaps this time would be different.

You know the feeling when you’re dating: you start to think, Maybe this guy doesn’t have a weird deal-breaker tucked away. Maybe he won’t turn out to have a strange collecting habit, a fixation on conspiracy theories, or admit he hasn’t read a book since high school. Maybe, just maybe, this person will finally restore your faith in finding someone who is both attractive and stable.

Spoiler alert: those guys always have a deal-breaker. Without fail. It’s simply a question of when they decide to reveal the particular brand of insanity they’ve been concealing beneath a charming façade.

The conversation flowed effortlessly throughout dinner. He told me about his accounting work—which, despite sounding dull, was actually engaging when he discussed the problem-solving involved and the satisfaction of helping small businesses manage their finances. I shared stories about my toughest design tasks and the rewarding experience of bringing a client’s vision to life through visuals.

We found out we both love hiking, though he preferred mountain trails while I favored coastal paths. We were both avid readers, though his taste leaned toward non-fiction while I was hooked on literary novels and the occasional guilty-pleasure romance. We both had complicated feelings about social media and were consciously trying to spend less time scrolling aimlessly.

When he spoke about his family, his voice held a genuine warmth. When he inquired about mine, he listened to my answers with what seemed like deep interest. When the couple next to us started a quiet disagreement, he discreetly suggested we focus on our conversation, giving them privacy rather than obviously eavesdropping, as some people do.

By the time we finished our main courses and were debating ordering dessert, I was feeling something I hadn’t felt in months: optimism about the prospect of a second date. Maybe even a third. Perhaps, if I was truly lucky, this could be the start of something genuine, lasting, and healthy.

Part 3: The Ignored Gut Feeling

When the bill arrived, delivered by our attentive waiter with a subtle nod and a smile, I automatically reached for my phone to book an Uber. This wasn’t about making a feminist statement; it was about personal safety and upholding the boundary I’d established after several awkward situations where first dates ended with uncomfortable negotiations at the front door and unwelcome assumptions about what the dinner might have entitled them to.

You see, I have a firm rule, forged through tough experience and supported by countless stories from friends who learned similar lessons the hard way: no rides home on a first date. It’s simply the safer choice and helps prevent any confusion about what level of intimacy might be expected in exchange for a meal and pleasant company.

Andy looked truly surprised to see me opening the Uber app. “What are you doing?” he asked, his brow furrowing in what looked like confusion, not offense.

“Just calling a ride home,” I explained, aiming for a casual, matter-of-fact tone. “Thanks for dinner, by the way. I had a wonderful time.”

“No chance,” he countered, leaning across the table to lightly touch my hand in a gesture that felt both protective and a touch too familiar. “A gentleman ensures his date gets home safely. That’s just basic consideration.”

Now, I really should have stuck to my rule. I absolutely should have, because rules like that exist for solid reasons, usually based on wisdom gathered from past mistakes. But Andy looked so sincere when he said it, and that smile was back—the one that had captivated me all evening, the one that made me forget all my carefully constructed dating boundaries and the lessons that inspired them.

There was something in his voice that suggested genuine concern for my safety, rather than an attempt to prolong the evening or angle for an invitation inside my apartment. He seemed almost insulted by the idea that I would use a ride-share service when he was perfectly capable of ensuring my safe return.

“I always drive my dates home,” he continued, his voice taking on an earnest quality that suggested this was a deep personal conviction. “It’s the right thing to do. Besides, I want to confirm you get inside okay. You never know who’s out there.”

So I gave in. Shame on me. I let him cover the dinner, accepted his offer to drive me, and told myself my safety rule was probably overly cautious anyway. After all, he’d been completely respectful all night, Marcus had vouched for him, and sometimes you have to take small, calculated risks if you want to form meaningful connections with other people.

The drive to my apartment took about twenty minutes through the quiet Saturday night streets of our city. Andy kept the chat light and relaxed, asking about my neighborhood and commenting on the lovely old trees lining my street. He didn’t try to extend the evening by suggesting a stop for coffee or drinks, didn’t ask probing questions about my living situation, and made no comments that hinted at an invitation inside.

He opened the car door for me again when we arrived, walked me to the main entrance, and waited patiently while I fumbled with my keys in that awkward way you do when you’re being watched and trying to look more composed than you feel.

“Thank you for a great evening,” he said, making no move to lean 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 the meal and for the ride home. That was truly kind.”

When I turned to wave from my living room window, he waved back, pulled away from the curb, and vanished into the night. I watched his taillights until they turned the corner, basking in that warm, satisfied feeling that comes from an evening that dramatically exceeded all expectations.

I went to bed that night feeling something I hadn’t felt in months: genuine hope for the possibility of finding love. Maybe even lucky to have met someone who seemed to understand that treating a woman well didn’t require grand gestures or huge expense, but just consistent respect and basic human kindness. Can you believe it? I honestly thought I might have found one of the good ones.

I lay there replaying the best moments—his laugh when I described my disastrous attempt at making homemade pasta, how closely he listened when I talked about my career, his genuine interest in my thoughts on everything from local politics to the best hiking routes.

For the first time in months, I fell asleep without scrolling through dating apps or wondering what profound flaw prevented me from connecting with anyone who wasn’t either dull or crazy, or both. Instead, I drifted off thinking about planning a second date and maybe, just maybe, the start of something real.

Part 4: The Utterly Baffling Bill

The following morning, Sunday, I woke up naturally around eight o’clock, feeling more rested and upbeat than I had in weeks. I made my coffee, checked my email, and was settling in with the Sunday crossword when my phone buzzed at precisely 7:13 AM with a notification that made me freeze and double-check the screen, convinced I was hallucinating from a caffeine deficit.

It was a PayPal request. Initially, I assumed it was spam—you know, those random payment requests scammers send, hoping busy people will accidentally approve them without looking. But when I opened the notification and saw Andy’s name attached to a detailed list of expenses, my brain simply stopped processing for a moment.

Are you prepared for this? Because I definitely wasn’t, even after staring at my screen for what felt like ages.

He had sent me an invoice. A genuine, itemized bill for the activities of the previous evening.

The breakdown read like a document from a ride-share service, except instead of a legitimate business charge, it was apparently Andy’s calculation of what I owed him for the basic courtesy of driving me home after a date he initiated and seemed to enjoy as much as I did.

• 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 thirty full seconds, trying to make sense of the visual evidence and wondering if this was some elaborate, sophisticated prank I was too simple to grasp. Was this Andy’s idea of a joke? Was he testing my reaction to see if I was a woman who could appreciate creative comedy? Was this a new dating trend I hadn’t heard about, like splitting the bill but for mileage?

But no, the PayPal request was absolutely serious, complete with a note that looked professionally composed: “Thanks for a wonderful evening! Please find the attached expenses for your safe transport home. Looking forward to our next date! – Andy”

Then I started laughing. Not just a giggle or a smile, but full-blown, doubled-over, tears-streaming-down-my-face laughter that echoed through my apartment and probably alarmed my neighbors. I laughed so hard I almost dropped my mug and had to sink onto my couch to avoid collapsing.

This man, who had seemed so utterly perfect just twelve hours earlier, had actually itemized the cost of fundamental human courtesy and billed me for it as if I were a client who had retained his services, rather than a woman he had taken on a date. Can you even fathom the thought process that led to this decision?

Imagine it: Andy, sitting in his presumably immaculate apartment with his accounting software and calculator, meticulously documenting every expense from our date, assigning a monetary value to gestures most people consider part of the basic social agreement of dating. Did he keep physical receipts? Did he measure the precise distance from the restaurant to my apartment to calculate the depreciation costs? Did he actually take a photo of the supposed puddle splash marks on his passenger-side door?

The cleaning fee was particularly noteworthy in its pure audacity. When exactly did these splash marks occur? I certainly hadn’t noticed any puddles on our short walk from the restaurant to his car. Had he inspected his vehicle after dropping me off and discovered some mysterious grime that he instantly blamed on my presence? Was this a standard fee he applied to every passenger, or had I been uniquely destructive during the twenty-minute drive?

I kept bursting into fresh waves of laughter every time I looked at the detailed list. The precision of it was almost respectable in its profound lack of social awareness. $4.75 for gas—not a rounded $5, but exactly $4.75, calculated, I assume, with mathematical exactness based on current fuel costs and the precise mileage. $3.50 for car depreciation, suggesting a formula for assessing the reduced value of his vehicle based on passenger miles traveled.

But it was the $20 parking fee that truly finished me. We had dined in a downtown area where street parking was explicitly free after six PM on weekends. I had specifically noticed this because I had been ready to offer to split the parking if necessary. Unless Andy had deliberately parked in some high-cost, premium garage I wasn’t aware of, that $20 fee was either entirely fabricated or represented his estimate of what his parking time was worth.

Part 5: The Flawless Counter-Invoice

After I’d finished laughing myself into a state of breathlessness, I decided that Andy’s business-minded approach to dating expenses deserved an equally creative and professional reply. If he was going to treat our romantic evening like a financial transaction, then I was going to teach him a lesson in superior customer service.

I opened my own PayPal account and sent him $50 with a message I painstakingly composed to achieve the perfect balance of sarcasm and feigned sincerity: “Thank you for itemizing your gentlemanly services! Here is $37.25 for your listed costs plus a $12.75 tip for door-opening, chair-pulling, and overall display of chivalry. 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 a man who sends his date a bill for the privilege of his company is not someone I needed to maintain contact with, regardless of how charming he had been over dinner.

But I wasn’t finished with the situation yet. Oh no. I was just getting started, because this story was too ridiculous to keep private, and Andy’s behavior was too egregious to ignore without some form of social consequence.

I instantly texted my brother: “UPDATE: The mystery of why your pickleball friend Andy is still single has been solved!” followed by screenshots of both Andy’s itemized invoice and my brilliant, sarcastic payment response.

I spent the rest of the morning on my couch, periodically erupting into fresh laughter every time I reconsidered different parts of Andy’s bill. The more I thought about it, the funnier it became. Had this been his plan all along? Was sending post-date invoices his regular method of operation? Did he maintain a complex filing system for tracking dating-related expenditures?

I started picturing Andy’s apartment filled with spreadsheets documenting every social interaction: “Lunch with co-workers: $12.50 for my half of the appetizers, $3.25 for excessive napkin use by colleagues.” “Family dinner: $8.75 for gas to parents’ house, $2.00 for wear and tear on formal shoes, $15.00 for the emotional toll of listening to Mom’s stories.”

Around noon, just as I was debating whether I should frame Andy’s invoice as a piece of abstract modern art for my apartment, Marcus called with the kind of stunned amusement in his voice that suggested he had been processing my screenshots for the last hour.

“Sarah, I am so, so sorry,” he started 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 chuckling occasionally. “I’m betting Andy reserves his special entrepreneurial charm for romantic encounters. I doubt he bills his pickleball buddies for sharing court time.”

“Actually,” Marcus said, and I could hear the gleeful storyteller tone creeping into his voice, meaning he had juicy gossip, “there’s more to this. 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 met his future wife.’”

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

“Yeah, well, when I showed the guys your screenshots, the whole group went dead silent for a good thirty seconds. Then Andy mumbled something I will never forget: ‘Well, chivalry doesn’t fund itself, you know.’”

“He did not say that.”

“He absolutely did. Word for word. And then, when the guys started demanding to know what he was thinking, he tried to defend himself by arguing that modern women should value transparency in dating expenses and that he was simply being honest about the actual costs of courtship.”

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

“I wish I were making it up, but Andy was entirely serious. He started explaining his dating philosophy, which apparently involves treating romantic relationships like business partnerships where all expenses must be equally shared. He claimed 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 gasping for air. “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 future dates for transportation, Andy said he was considering establishing a comprehensive dating fee structure that would include charges for restaurant recommendations, conversation quality, and what he called ‘emotional labor overhead.’”

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

“The crowning moment was when someone asked him if he expected women to tip based on date satisfaction, and Andy got this reflective look on his face like he was genuinely 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 decided that Andy’s place in their social circle was no longer welcome.

“I mean, we all knew he was a bit particular about money,” Marcus clarified, “but none of us realized he was totally unhinged about it. Who sends their date a bill? Who thinks that’s normal adult behavior?”

I had to admit, that felt incredibly satisfying. Not because I wanted Andy to lose his friends, but because it validated my feeling that his behavior was as utterly outrageous as I’d thought, and that other people found it equally unacceptable

Part 6: The Story Spreads Online

But here is where my story takes a truly wild turn, and where I realized that Andy’s accounting-based approach to romance was apparently far more prevalent than any of us had imagined.

It was the following weekend. I was going through my usual Saturday morning ritual: lounging on my sofa in my most comfortable pajamas, coffee within arm’s reach, diligently scrolling through TikTok like someone whose only pressing concern was whether to order groceries online or brave the outside world.

Suddenly, I gagged on my coffee and nearly dropped my phone when a video popped up on my feed, making me wonder if I was experiencing severe déjà vu or if the universe had decided to prank me spectacularly.

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

The specific amounts were a little different from what I’d received, but the incredible level of audacity and entitlement was exactly the same. Gas expenses, car depreciation calculated to the cent, parking fees, and—this detail was new—a line item for “cologne and grooming preparation: $15.00,” which suggested Andy had been actively improving his billing system based on previous customer interactions.

“This guy genuinely thinks he’s Uber with a dinner side order,” the woman stated in the video, holding up her phone to display Andy’s PayPal request. “He actually charged me for the honor of sitting in his car and breathing his air. I’m fairly certain this violates several dating standards and possibly some kind of consumer protection laws.”

I was astonished. Andy had done this before. This wasn’t a bizarre, isolated lapse in judgment caused by our particular date or some kind of accounting brain failure brought on by tax season pressure. No, this was Andy’s deliberate dating strategy, his systematic method for romantic relationships that apparently involved converting every social outing into a billable consulting session.

The comments section was ruthless, and I devoured every single savage reply:

“Ladies, avoid Andy’s Taxi & Misogyny Service – now featuring surcharges for emotional labor!”

“At least Uber drivers sometimes offer mints and a phone charger. This guy just offers pure entitlement.”

“This man literally said, ‘Compensate me for acting like a decent person.’ Sir, that is not how basic manners work.”

“Plot twist: He’s actually collecting interest on all these invoices and trying to build a dating empire.”

“Next thing you know, he’ll be demanding a security deposit before the appetizers.”

I immediately forwarded the video to Marcus with a simple message: “Your former pickleball associate is now TikTok famous, and for all the wrong reasons.”

His reply was instantaneous and full of mortification: “I am permanently retiring from judging men’s character. Also, I am finding a new pickleball group immediately.”

I spent the rest of the afternoon deep in the comments and sharing the video with my friends, which quickly turned into a massive group chat about dating nightmares that lasted hours. It felt like opening the floodgates on years of frustration with men who had exposed their complete unsuitability for adult relationships through various forms of shocking behavior.

My friend Jessica shared a story about a guy who had billed her for the gas he used driving to pick her up, then got upset when she didn’t also reimburse him for his time spent grooming. My friend Lauren told us about a man who meticulously calculated the precise cost of the drinks he bought her and then deducted that exact amount from her payment when she did freelance graphic work for his company.

It evolved into this incredibly therapeutic shared experience about all the ways that certain men reveal their true selves through their attitudes toward finances, courtesy, and basic respect. And honestly? It was hugely validating to recognize that Andy’s specific behavior was just one part of a wider pattern of entitled absurdity that women everywhere were dealing with.

The TikTok video ultimately achieved over two million views and generated dozens of response videos from other women sharing their own experiences with men who had similarly turned dating and romance into a transaction. There were stories about guys who charged for parking, who calculated restaurant tips to the penny and expected their share back, and even one memorable tale about a man who had created a spreadsheet tracking the cost of every single text message he sent.

Part 7: Identifying the Broader Problem

What intrigued me most about the viral reaction to Andy’s bizarre invoicing method was how it brought to light a much broader cultural conversation about dating, gender expectations, and the sense of entitlement that some men feel regarding women’s time, attention, and appreciation.

The comments on the TikTok video weren’t simply making fun of Andy’s unique brand of romantic finance—they were dissecting the fundamental assumption that women somehow owe men a form of compensation for simple courtesy, and that chivalry is a paid service rather than an automatic expression of mutual human respect.

“This is the result when guys think of treating women like people as a favor they’re doing, instead of the baseline expectation of decency,” one person wrote.

“He is literally charging her for the privilege of existing in his vicinity. The lack of self-awareness is breathtaking,” wrote another.

“Just imagine being so entitled that you believe opening a car door creates a financial debt that must be settled via PayPal,” added a third.

The discussion quickly moved beyond Andy’s specific invoice to include larger topics concerning men who maintained detailed mental records of every nice thing they did for women, expecting excessive gratitude and reciprocation for gestures that should have been automatic signs of consideration.

Women shared numerous accounts of dates who insisted on splitting dinner checks down to individual appetizer portions, men who complained about the cost of flowers or cinema tickets as if these were unexpected business expenditures rather than choices they freely made, and guys who treated every act of politeness like an investment that needed to guarantee a financial or emotional return.

What stood out to me was how many women had experienced some version of Andy’s behavior—perhaps not with an itemized bill, but certainly the strong feeling that certain men viewed dating as a transactional relationship where women were expected to provide compensation (be it emotional, physical, or financial) for male attention and effort.

I started reflecting on all the times I’d felt obliged to show disproportionate gratitude for basic manners, to suppress my own preferences to avoid being labeled high-maintenance, or to accept behavior that made me uncomfortable simply because a man had spent money on a meal or driven me somewhere or performed some other action that was supposedly generous but ultimately felt like a future obligation being manufactured.

The massive response to Andy’s invoice story became a crucial turning point for thousands of women to re-examine their own dating histories and recognize patterns of entitlement and manipulation that they had previously dismissed as merely normal or unavoidable.

“I just realized my ex always used to keep a precise record of every nice thing he did for me and throw it back at me during arguments,” one woman commented. “He treated kindness like a credit system where I constantly owed him points.”

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

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

The more I read, the clearer it became: Andy’s invoice wasn’t just a funny anecdote—it was a perfect symbol of a entitled mindset that countless women had encountered in various forms throughout their dating lives.

Part 8: Essential Takeaways

Looking back on the entire Andy saga now, several months later, I’m actually glad it happened. Not because I enjoyed being billed for the honor of his company, but because it provided me with several valuable lessons about setting boundaries, dating expectations, and ultimately, trusting my own intuition.

First, I learned that my rule about arranging my own transportation after first dates is in place for excellent reasons that extend beyond just physical safety. When someone pushes to drive you home, they aren’t just offering a kind gesture—they are creating a situation of dependence, a sense of obligation, which instantly shifts the power dynamic in their favor.

Andy’s insistence on driving me wasn’t truly about my safety, as I’d initially believed. It was about creating a moment to later claim he had provided a specific service that warranted financial compensation. Had I stuck to my original plan and called an Uber, he would have had no foundation for his ludicrous invoice, and I would have avoided the whole ordeal.

The experience taught me to trust that tiny, cautionary voice in my head that raises a flag when something feels wrong, even if I can’t immediately explain why. When Andy insisted on the ride, a part of me felt uneasy, but I dismissed that instinct because his logic sounded reasonable and his intentions appeared pure. Now I understand that feelings of unease often pick up on subtle cues that our conscious minds haven’t fully registered yet.

Second, I learned that genuinely generous people don’t keep score. When someone sincerely wants to do something kind for you, they don’t track their efforts or anticipate specific returns on their time or money. They certainly do not 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 genuinely cared about my comfort or happiness; he had been building up billable hours that he intended to cash in later.

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

Third, I learned that a person’s response to rejection or disappointment tells you absolutely everything you need to know about their character. When Andy realized that I wasn’t going to be charmed by his entrepreneurial take on dating expenses, when he discovered that others found his behavior unacceptable, his reaction was to double down on his entitlement instead of reflecting on his actions.

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

The experience also highlighted the power of sharing stories and refusing to deal with unacceptable behavior in private. By informing Marcus about the invoice, by sharing the screenshots with my friends, and by participating in the wider conversation that erupted on social media, I helped create a space where other women could recognize similar patterns in their own lives and feel validated in their reactions to unacceptable behavior.

Sometimes we second-guess our own reactions to situations that feel fundamentally wrong but that others might dismiss as harmless or just normal. Andy’s invoice felt outrageous to me, but a part of me wondered if I was overreacting, if this was some modern dating trend I didn’t grasp, or if I was being unreasonable in my shock.

The viral reaction to the TikTok video confirmed that my reaction was not only appropriate but was shared by millions of people who immediately recognized Andy’s behavior as manipulative, entitled, 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 personal relationships.

Part 9: Looking Ahead

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

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

Marcus, for his part, has become substantially more cautious about his matchmaking efforts. The Andy incident taught him that superficial interactions with people don’t reliably reveal their core character, and that vouching for someone’s romantic suitability requires a deeper understanding than can be gathered from weekend pickleball matches.

“I think I’m going to stick to making work contacts and leave the dating referrals to actual dating experts,” he told me recently. “Clearly, my judgment regarding men’s fitness for romance is questionable at best.”

The Andy story has become legendary among our friends, a favorite anecdote brought out at dinners and gatherings whenever someone needs a sharp reminder that dating horror stories can always get worse, or whenever someone needs a boost to trust their instincts about questionable behavior from potential partners.

But more than just providing entertainment, the story serves as a cautionary tale about the importance of establishing boundaries, spotting red flags, and understanding that someone’s actions toward you reveal their true character far more clearly than their charm or carefully chosen words.

Finale: The Clarity Gained

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

“I honestly thought I was the only one,” she wrote. “I thought maybe there was something wrong with me for being so offended by his bill. Seeing that he’d done the exact same thing to other women helped me realize that this was a fixed pattern of behavior, not a single mistake or a joke that I just didn’t get.”

She went on to tell me that several other women had reached out to her after seeing her video, sharing their own stories about Andy’s invoicing system and revealing that his dating expenses billing had been ongoing for over a year. Apparently, he had been actively 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 concluded that his personal preparation time should be billed at a consulting rate.”

The revelation that Andy had been systematically billing women for dating expenses for over a year was both shocking and, in a strange way, deeply satisfying. It confirmed that breaking things off was absolutely the correct decision, and it provided closure that his behavior hadn’t been triggered by anything specific about me or our interaction.

More importantly, it reinforced the powerful 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 achieved viral status, if women hadn’t started commenting about their own encounters with entitled men, Andy might have continued his romantic entrepreneurship indefinitely.

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

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

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

But I am also completely comfortable being single until I find someone who treats kindness as a natural extension of their character rather than a billable service that requires compensation. Because thanks to Andy, I now know the difference, and I will never settle for less than I deserve again.

The wildflowers Andy brought me on that first night lasted about a week before they wilted and I had to dispose of them. But the lesson he taught me about trusting my instincts, setting clear boundaries, and recognizing genuine character—that lesson will last forever.

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

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