It was when Lucas insisted on paying for our first date that I realized I had finally met a gentleman worth my time. Thoughtful gestures, roses, and effortless charm—he seemed like the perfect candidate. Naturally, I expected butterflies when his text arrived the next day. Instead, the moment I read it, my stomach sank.
Honestly, I hadn’t given much thought to the idea of my best friend Tessa setting me up. She always had good intentions, but matchmaking had never been her forte. Truthfully, I wasn’t in any rush to date anyway. Yet Tessa was relentless.
“He is absolutely perfect, Julia. A gentleman in every sense,” she said over the phone one Thursday evening while I stood in front of my closet, tugging hangers in frustration. “You’re going to thank me later.”
“You’ve never set me up before,” I reminded her, clutching a blue dress and eyeing myself suspiciously in the mirror. “I’ve never been set up. How do you even know what I like?”
“Because I’ve known you since we were thirteen,” she replied confidently. “And Owen believes in him too. They’ve been friends forever.”
I was surprised. Owen, Tessa’s calm and level-headed boyfriend, rarely gave casual endorsements. If he vouched for Lucas, there had to be something trustworthy there.
I sighed—half to her, half to myself. “Fine. But at least show me a photo so I know I’m not walking into a disaster.”
Moments later, my phone pinged with a picture.
Lucas was… attractive. Dark, neatly trimmed hair, a well-groomed beard, and a smile that reached his eyes. Not Hollywood-level, but charming in a reliable, approachable way.
“Alright,” I admitted reluctantly. “He’s cute.”
“Oh, I told you!” Tessa squealed. “Text him. Go on. You won’t regret it.”
I followed her advice and agreed to meet him at a new Italian restaurant downtown, overlooking the river. Not overly fancy, but enough to show it mattered.
I arrived five minutes early, checking my reflection one last time and taming a rebellious strand of hair. Then I saw him walking toward me—tall, confident, smiling, and holding a bouquet of roses. Not grocery-store roses, but carefully arranged, ribbon-tied blooms. My heart skipped.
“You must be Julia. These are for you,” he said, handing me the flowers.
Blinking in surprise, I replied, “Wow, thank you. You didn’t have to do that.”
“I wanted to start the night off right,” he said. Before I could respond, he pulled a small gift box from his jacket pocket, wrapped with a bright teal bow.
“What’s this?” I asked, raising an eyebrow.
“Just a little something. Open it,” he said, clearly pleased with himself.
Inside was a polished silver keychain, engraved with the letter “J.” Simple, elegant, and oddly intimate.
“I asked Tessa what you’d like,” he explained.
I was stunned. Personalized gift plus flowers? Either he was a master of first impressions or genuinely interested.
“This is thoughtful,” I murmured.
He smiled, offered his arm, and led me inside. From the start, he was attentive—pulling out my chair, holding doors, maintaining eye contact, asking intelligent questions, and laughing easily at my stories. He remembered small details from our messages, making the evening feel effortless.
Over wine, he asked, “So, why’d you agree to this setup?”
I chuckled. “Tessa’s persuasive. Plus, she and Owen vouched for you, so I figured I’d give it a shot.”
“They make a great couple,” he said, nodding. “Owen and I have high standards. He’s one of the good ones.”
Conversation flowed naturally—true crime podcasts, offbeat films, and stories from his marketing job that were funny and frustrating at the same time. I found myself relaxing, genuinely enjoying the night.
By dessert, I was already thinking this could be one of the best first dates I’d ever had. When the check arrived, I reached for my purse out of habit.
But Lucas was quicker, sliding his card into the folder before I could unzip my bag.
“Absolutely not,” he said firmly. On a first date, he insisted on paying. His tone was decisive, not joking.
I hesitated, then smiled. “Alright, if you insist. Thank you.”
He walked me to my car and asked if he could call me again.
“I’d like that,” I admitted.
As I drove home, cautiously optimistic, I reflected on the roses, thoughtful gift, and gentle attention. The next morning, my phone pinged with a notification—but not a sweet text. It was an attachment.
Curious, I brewed coffee, climbed back into bed, and opened it.
It was an invoice. A professionally formatted invoice:
Date Night Invoice
Amount Due: One outstanding balance
Services rendered:
Roses in a bouquet: one embrace
Coffee date, plus custom keychain gift
Taking a selfie together while opening the car door
Holding hands and pulling out chairs at the next date
Compliments, attentive conversation, full dinner, and tip
Terms: Payment expected in full. No refunds. Non-compliance may be forwarded to collections (Owen will be informed).
Jaw on the floor.
I screenshot it and sent it to Tessa. Seconds later, she replied, laughing: “Oh my God! Presenting this to Owen now. Wait till he sees it!”
Five minutes later, Owen called, laughing so hard he could barely speak.
“Lucas invoiced you?” he wheezed. “He’s always been… creative about dating, but this is next level.”
Eventually, Owen retaliated, sending me his own mock invoice:
Lifetime of Silence Invoice
Introduce yourself to a beautiful woman: one block
Convince her you’re a gentleman: measured dose
Formal apologies to every woman ever allowed to sit at your table
Instantaneous payment required; non-compliance may lead to public shaming
Tears streamed down my face from laughing. I texted Owen: “This is perfect.”
“Done,” he replied.
Soon after, Lucas sent annoyed messages, but I blocked them with a thumbs-up.
Tessa called later, still laughing. “Jules, this story will be told at every party for the next decade.”
She might have been right.
Reflecting on that night, I realized one lesson in dating: if a man insists on paying, make sure he isn’t planning to invoice you later.
And the silver keychain? I kept it—not as a reminder of Lucas, but as a hilarious memento of the strangest, funniest first date of my life.