My Date Insisted on Paying the Bill – I Wish I Hadn’t Let Him
When Eric insisted on picking up the tab on our first date, I was thrilled to meet such a chivalrous man. Between his romantic gestures with roses and sparkling conversation, I thought I had hit the jackpot. However, the message I received the next day revealed a surprising twist.
My good friend Mia had never played the role of matchmaker before, so when she suggested setting me up with someone, I was skeptical.
“Kelly, he’s great! A real gentleman. You have to meet him,” Mia urged as I rummaged through my wardrobe.
I reminded her, “You’ve never set me up before. How do you know he’s my type?”
“I just do,” she replied confidently. “Chris swears by him. He’s been friends with Eric for years.”
Mia’s boyfriend, Chris, was known for his good judgment, so hearing his endorsement got my attention.
“Okay,” I conceded, “at least send me his picture.”
Soon after, my phone alerted me to a new message.
The picture featured a well-dressed, clean-cut man with a smile that felt genuine even through a screen.
“Alright, he looks good,” I admitted to Mia.
“I told you so! Now message him and set up a date. You won’t regret it,” she promised.
After exchanging some lighthearted texts, Eric and I decided to meet at a quaint Italian restaurant by the river, perfect for a first meeting.
Arriving early, I nervously checked my reflection when I saw him approaching the restaurant, armed with a bouquet of roses.
His presence was reassuring, with a confident air about him that matched his photo in real life.
The roses he offered weren’t just any store-bought flowers; they were a carefully arranged bouquet.
“You must be Kelly,” Eric said warmly, handing me the flowers. “These are for you.”
“Thank you,” I replied, pleasantly caught off-guard. “You shouldn’t have.”
“I wanted to start the night off right,” he stated, then surprised me with a small, elegantly wrapped gift box.
“What’s this?” I asked, raising an eyebrow.
“Just a little something,” he encouraged, smiling.
Inside was a sleek silver keychain engraved with ‘K’—a simple yet thoughtful gesture.
“It’s just for you,” he explained. “I asked Mia what you might like.”
That gesture impressed me. A meaningful gift on a first date is rare and memorable.
“This is lovely,” I expressed, genuinely moved. “Thank you.”
Eric was the perfect gentleman that evening, even holding the door and pulling out my chair.
He showed genuine interest in my work, remembered little details of my life, and made me feel special.
After we ordered our meals, he asked, “What made you go ahead with the setup?”
“Mia’s very convincing,” I laughed. “And with both Mia and Chris recommending you, it was hard to say no.”
“Those two are great,” he agreed. “Chris and I go way back. He’s a good judge of character.”
Conversation flowed seamlessly, as though we had known each other for a long time.
We shared an interest in true crime podcasts and odd documentaries, and his stories about his marketing career were engaging.
It felt like one of the best first dates I’d experienced.
When the bill arrived, I naturally reached for my wallet.
“No way,” Eric declared, placing his card firmly on the bill before I could make a move. “I believe a man should always pay on the first date.”
His tone was courteous yet direct, as if stating a lifelong principle.
I hesitated for a moment, then relented. “If you insist,” I smiled, “thank you.”
A free meal is always nice, especially when paired with pleasant company. We left the restaurant, and he asked if he could call me again.
“I’d like that,” I replied sincerely.
He hugged me goodbye—neither too intimate nor too aloof—which made our farewell perfect. Driving home, I felt it had been a remarkable first date.
The following morning, I was surprised to see a notification from Eric. Expecting a sweet “I had a great time” text, I found an attachment instead.
Intrigued, I opened it, picturing a memento from our evening.
To my shock, it was an invoice! A professionally made, detailed invoice.
Sitting at the top of the page, in bold font:
Date Night Invoice – Amount Due: 1 Outstanding Balance.
The list that followed was surreal: – Bouquet of Roses: 1 hug – Custom Keychain Gift: 1 coffee date (scheduled within one week) – Opening Car Door: A cute selfie together – Pulling Out Chair: Holding hands on the next date – Full Dinner + Tip Covered: A second date, no excuses
It seemed too ridiculous to be serious, yet one glance at the bottom confirmed that he was very earnest.
Payment is expected in full. No refunds. Noncompliance will lead to collections (Chris will hear about it). Looking forward to your prompt payment!
I was flabbergasted.
Expecting non-monetary “payments” in return for his actions was audacious and troublesome. Who on earth thinks like that?
I quickly sent Mia a screenshot of the invoice, and her response was immediate.
“OH MY GOD. I’M SHOWING THIS TO CHRIS NOW!”
“Is this real life???” I texted back, incredulous. “He’s serious!”
“Hold on, Chris has to see this. He’s going to LOSE IT,” she replied.
Five minutes later, my phone rang.
It was Chris, laughing hysterically.
“Kelly, I can’t believe it,” he said in between laughs. “I’ve known Eric forever, and this is out of left field.”
“So, it’s not a prank?” I inquired.
“Absolutely not,” Chris confirmed. “Eric’s always been a bit intense about relationships, but this tops it. Time for payback!”
Chris’ knack for clever responses shone through his plan: to create an identical invoice with creative charges.
After drafting it, Chris sent his version to me, and it was hilarious.
Service Invoice – Amount Due: A Lifetime of Silence – Introducing You to a Gorgeous Woman: 1 permanent block on all platforms – Convincing Her You Were a Gentleman: Time for self-reflection on why you’re single
Letting You Sit at the Same Table: A heartfelt apology to all past dates – Not Exposing You Online: A generous courtesy Payment is required IMMEDIATELY, or humiliation will ensue. Cheers!
“This is genius!” I texted, amused. “Send it to him!”
“Sent!” he replied promptly.
Soon, I received multiple messages from Eric—each angrier than the last.
“Very mature.”
“Just managing expectations, not everyone is loaded.”
“Chris isn’t a good friend.”
“You missed out on a GREAT guy.”
I didn’t see the point in replying to someone who viewed relationships transactionally, so I sent a thumbs-up emoji and blocked his number.
Later, Mia called, still laughing over the incident.
“I’m sorry,” she said. “I thought he was normal. Chris had no clue Eric was like this either.”
“No worries,” I said, surprising myself with how unfazed I felt. “It’s a fantastic story.”
“True! This will make the rounds at every party for the next ten years,” she chuckled.
I learned a valuable dating lesson: if someone insists on paying, ensure you’re not billed for it later. Though odd, the keychain remains an amusing memento of the bizarre date.
The story echoed in my thoughts: a bride at her wedding received a startling objection from the past, threatening her perfect moment. Would she address this, or let a secret unravel her dreams?
This piece draws inspiration from real-life, though fictionalized for creative enhancement. Details, events, and characters are altered for privacy, and resemblance to actual events or people is coincidental and unintended.
The author disclaims the factual accuracy and any character portrayal, as these stories serve as entertainment with personal opinions attributed solely to characters.
