It was when Lucas insisted on paying for our first date that I realized I might have finally met a gentleman worth my time. Thoughtful gestures, roses, effortless charm—he seemed perfect. Naturally, I expected butterflies when his text arrived the next day. Instead, my stomach sank.
Honestly, I hadn’t given much thought to my best friend Tessa setting me up. She always had good intentions, but matchmaking wasn’t her strong suit. And truthfully, I wasn’t in a rush to date. Yet Tessa was relentless.
“He’s absolutely perfect, Julia. A gentleman in every sense,” she said 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, holding a blue dress and eyeing myself suspiciously. “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.”
Owen rarely gave endorsements casually. If he vouched for Lucas, there had to be something trustworthy there.
I sighed. “Fine. At least show me a photo so I know I’m not walking into a disaster.”
Moments later, my phone pinged.
Lucas was… attractive. Dark hair, neatly trimmed beard, a smile that reached his eyes—not Hollywood-perfect, but warm, approachable, reliable.
“Alright,” I admitted. “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, taming a rebellious strand of hair, when I saw him walking toward me—tall, confident, smiling, 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.
“Wow, thank you. You didn’t have to do that,” I said.
“I wanted to start the night off right,” he replied. 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.
Inside was a polished silver keychain, engraved with the letter “J.” Simple, elegant, 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, remembering details from our messages, laughing easily at my stories. The evening felt 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.”
“They make a great couple,” he said. “Owen and I have high standards. He’s one of the good ones.”
Conversation flowed—true crime podcasts, offbeat films, his marketing job anecdotes. I found myself relaxing, genuinely enjoying the night.
By dessert, I was thinking this could be one of the best first dates I’d ever had. When the check arrived, I reached for my purse.
Lucas was quicker, sliding his card in before I could unzip my bag.
“Absolutely not,” he said firmly. First date, he insisted on paying. His tone was decisive.
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.
The next morning, my phone pinged—not a sweet text, but an attachment.
Curious, I brewed coffee, climbed back into bed, and opened it.
It was an invoice. Professionally formatted:
Date Night Invoice
Amount Due: One outstanding balance
Services rendered:
-
Roses in a bouquet: one embrace
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Coffee date, plus custom keychain gift
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Taking a selfie together while opening the car door
-
Holding hands and pulling out chairs at the next date
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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, but this is next level.”
Owen retaliated with his own mock invoice:
Lifetime of Silence Invoice
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Introduce yourself to a beautiful woman: one block
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Convince her you’re a gentleman: measured dose
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Formal apologies to every woman ever allowed to sit at your table
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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.
Lucas sent annoyed messages later, but I blocked them with a thumbs-up.
Tessa called, 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.