hen my best friend Mia told me she wanted to set me up with her boyfriend’s friend, I hesitated. Blind dates weren’t really my thing. I had tried them once or twice in the past, and each attempt had ended awkwardly, with uncomfortable silences and a lingering sense of disappointment. There’s always that invisible pressure to perform, to be witty or charming while judging someone else’s every move — and I had never been very good at it. But Mia was insistent. She had this way of speaking that made it sound like refusing her was impossible, like I’d be letting down the universe itself. “You’ll love him,” she said. “He’s polite, smart, stable — a total gentleman.” I could practically hear the spark of excitement in her voice, and for reasons I couldn’t fully explain, I agreed, against my better judgment.
His name was Eric. From the very first message, he came across as confident but not pushy — a subtle quality that was immediately refreshing. He didn’t send the usual “hey” or “sup” that most people do. Instead, he wrote full sentences, asked thoughtful questions, and responded with enough detail to make it feel like he genuinely wanted to get to know me. Over the next week, our texts flowed easily, moving from casual small talk to deeper conversation about travel, favorite books, childhood memories, and the universal horror of Tinder. After seven days, he suggested dinner at a nice Italian place downtown. I hesitated for only a moment before saying yes, rationalizing that it was just dinner — no pressure, no expectations.
The night of the date, Eric showed up early. He was holding a bouquet of roses, which immediately made me blush, and wore a crisp button-down that looked effortlessly put together. There was a practiced smile on his face, the kind that suggested charm but somehow didn’t feel fake. “These are for you,” he said, handing me the flowers. The gesture felt thoughtful, not performative. Inside the restaurant, he pulled out my chair, complimented my dress with a specificity that made it clear he had noticed details, and handed me a small keychain with my initial engraved on polished metal. I remember thinking, Wow, maybe Mia was right. He seemed like the kind of man who actually understood effort, someone who didn’t take basic gestures for granted.
Over dinner, conversation flowed with an ease I hadn’t anticipated. We talked about everything: places we wanted to visit, bizarre encounters on dating apps, and how we both missed movie theaters that didn’t charge a fortune for popcorn. Eric laughed easily, without trying too hard to impress, and I found myself relaxing into a space that felt unexpectedly safe. The food was good, but it wasn’t what made the evening memorable — it was the way he listened, the way he responded thoughtfully, and the subtle attentiveness that made me feel genuinely seen.
When the bill arrived, I instinctively reached for my purse. Eric waved me off. “A man pays on the first date,” he said, sliding his card to the waiter with a confidence that bordered on old-fashioned charm. It felt performative, maybe, but also strangely reassuring. I couldn’t argue with that — it was a simple gesture that, at the time, seemed romantic.
After dinner, we walked out together. Eric offered me his arm as we strolled to my car, speaking easily about upcoming events and future travel plans. He waited until I started the engine before heading off, which left me with a strange sense of nostalgia for a time when dating had felt simpler, more respectful, less transactional. On the drive home, I texted Mia: You might actually be right about this one.
The next morning, I woke up smiling. I expected a cute “Had a great time” text — maybe a short message expressing gratitude or interest in seeing me again. Instead, I found something that made my stomach drop: an email with the subject line, Invoice for Last Night.
I thought it was a joke at first. Maybe a meme or a playful reference to the dinner bill. But when I opened it, the content made my jaw drop. It wasn’t a joke. It was a professional-looking, perfectly formatted document — logo, tables, detailed “services,” and a total amount due. Each line item was an attempt to quantify parts of our evening:
Dinner: $120, covered in full
Flowers: “In-kind gesture — requires reciprocation (one hug)”
Keychain: “Personalized gift — repayable via coffee date”
Emotional labor: “Holding hands next time to express appreciation”
At the bottom, in bold: “Failure to comply may result in Chris hearing about it.”
Chris — as in Mia’s boyfriend. Eric’s friend.
I stared at the screen, disbelief and disgust colliding. This wasn’t humor; it was a calculated attempt to assert control, to turn affection into currency, and to weaponize my friend’s boyfriend as leverage. I immediately texted Mia: You’re not going to believe this. Within minutes, I forwarded the email. Her reply came almost instantly: Oh my god. He’s insane. Don’t answer him.
But Mia, being Mia, didn’t stop there. She looped in Chris. To his credit, Chris was both horrified and eager to retaliate. Together, they hatched a plan to give Eric a taste of his own medicine. Later that afternoon, Chris sent Eric his own “invoice,” equally professional-looking, complete with mock legal jargon and a company logo reading Karma & Co.
The charges were hilarious, absurdly on point:
Emotional disturbance fee: For making a woman uncomfortable
Public embarrassment surcharge: For acting like a creep on a first date
Service charge: “For sitting at the same table as someone out of your league”
At the bottom, in bold: “Failure to comply will result in permanent reputation damage. No refunds.”
Eric completely lost it. He sent a flurry of texts alternating between anger, self-pity, and indignation:
“You’re overreacting.”
“It was supposed to be funny.”
“You just can’t take a joke.”
“You missed out on a great guy.”
I didn’t reply. Instead, I sent a single thumbs-up emoji and blocked him.
That night, Mia called, laughing so hard she could barely speak. “I’m so sorry,” she gasped. “I swear, I had no idea he was that unhinged.”
Honestly, I wasn’t even mad. I was relieved. Not every day do you see someone’s true character on the first date. What Eric had intended as cleverness revealed controlling behavior, manipulation, and entitlement — traits that were probably hidden behind his charm. If that invoice hadn’t arrived, I might have wasted weeks pretending everything was fine.
Later, I reread the email, trying to understand his thought process. Was it power? Ego? Arrogance disguised as humor? Likely all of the above. The attention to detail — layout, wording, professionalism — suggested planning. This wasn’t a spur-of-the-moment prank; he either had done this before or at least thought about it extensively. He expected me to laugh, play along, or feed his need for control. Instead, I did the one thing he couldn’t manipulate: I ignored him.
In the days that followed, Mia and Chris cut him off completely. Eric doubled down when confronted, claiming I was “too sensitive” and that “women don’t appreciate humor anymore.” Classic deflection. Meanwhile, my phone stayed blissfully quiet. No more “gentleman.” No more invoices. Just peace.
Looking back, I can even appreciate the absurdity. The night had started like a romantic comedy — roses, charm, laughter — and ended like a cautionary tale about modern dating and entitlement. I learned a valuable lesson: pay attention to the small red flags before they escalate. Anyone who sees kindness as debt is manipulative, not romantic.
Now, when someone asks about my worst date, I don’t hesitate. “The one who sent me an invoice,” I say, grinning. It always earns a laugh, and I make sure to add, “And he really thought I’d pay.”
Truthfully, I did pay — just not in the way he expected. I paid attention, and that was worth far more than any dinner bill. I gained clarity, perspective, and a story I’ll never forget.