My Date Insisted on Paying the Bill – I Wish I Hadn’t Let Him

Eric volunteered to cover our first date expenses. I believed I had encountered a real gentleman. He brought roses and a thoughtful present. Our conversation flowed naturally. He seemed to fulfill all my expectations.

The following day brought a text from him. I anticipated a pleasant follow-up message. My heart sank as I read his words.

Mia wanted to help by arranging a blind date. Her matchmaking experience was nonexistent. She had good intentions.

“Eric is extremely kind, Kelly! A complete gentleman. You will adore him,” Mia declared during our phone call. I searched through my wardrobe at the same time.

“You have never arranged dates for me before,” I pointed out. “How do you know what I prefer?”

“I understand you better than anyone else,” she answered with certainty. “Also, Chris supports him. They have been friends for many years.”

This information made me reconsider. Chris was Mia’s partner. He could judge people well. His approval of Eric suggested potential.

“Alright,” I agreed reluctantly. “Let me see his photo first.”

My phone buzzed seconds later with a new message.

The man in the picture looked decent. He appeared well-groomed and properly dressed. His genuine smile extended to his eyes.

“He is attractive,” I confessed.

“I told you so!” Mia exclaimed excitedly. “Send him a message and arrange the meeting. You will not be disappointed.”

Several casual messages led to dinner plans. We chose a new Italian restaurant overlooking the river. The venue was pleasant without being overly formal for a first meeting.

I reached the location five minutes before our scheduled time. I waited by the entrance as we had planned. I used my phone camera to check my appearance nervously. Then I saw him walking toward the restaurant.

My heartbeat increased slightly. His photo had been accurate. He possessed that neat, professional appearance. He moved with self-assurance.

The roses in his hands surprised me completely. These were not simple store-bought flowers. He carried a professional arrangement with a ribbon.

“You are Kelly,” he stated, showing the same warm expression from his photograph. “These belong to you.”

“Thank you so much,” I responded with genuine surprise as I took them. “This was unnecessary.”

“I wanted to begin our evening properly,” he explained, presenting the flowers to me.

He withdrew a small gift box from his coat pocket. A cyan ribbon decorated the package.

“What could this be?” I inquired, raising my eyebrows with astonishment.

“Simply a minor token. Please unwrap it,” he urged.

The box contained an elegant silver keychain. The letter “K” was carved into its surface. The item showed careful consideration and personal attention.

“Created specifically for you,” he stated effortlessly. “I consulted Mia about your preferences.”

His gesture truly amazed me. Flowers plus a considerate present for our initial meeting? This gentleman was clearly sending a message. He was either genuinely attracted or excelled at making first encounters memorable.

“Your kindness surprises me,” I expressed with sincere appreciation. “I am grateful.”

Eric maintained his courteous behavior flawlessly. He held doors open, assisted with my chair, and kept consistent visual contact during our discussion. He posed meaningful questions about my graphic design career. He recalled family details I had briefly mentioned in our text exchanges. He made me feel like the most captivating individual present.

“What convinced you to accept this arranged meeting?” he inquired after we placed our food orders.

“Mia possesses strong persuasion skills,” I chuckled. “Additionally, both she and Chris recommended you, which happens infrequently.”

“They make an excellent pair,” he agreed. “Chris and I share history from university days. He has always demonstrated integrity.”

Our discussion continued smoothly from that point.

We found common ground in crime podcasts and documentaries about unusual communities. He shared entertaining workplace stories from his marketing position. I found myself considering this could be my finest first date experience.

The bill arrived, prompting me to reach for my handbag.

“Definitely not,” Eric stated decisively, placing his payment card on the check holder before I could access my purse. “Men cover expenses on first dates.”

His manner caught me off guard slightly. He spoke with authority rather than mere politeness, as if stating an absolute principle. I hesitated briefly, then accepted.

“Very well, since you demand it. Thank you.”

I chose not to dispute a complimentary dinner, particularly after such an enjoyable night.

We departed together. He inquired about calling me again shortly.

“I would enjoy that,” I responded truthfully.

He embraced me farewell. The gesture balanced friendliness with interest perfectly while avoiding any awkwardness. I traveled home wearing a grin, considering this among my finest first dates ever.

The following morning brought a notification from Eric. My drowsy mind anticipated a sweet “wonderful evening” message. Instead, I discovered an attachment.

I prepared coffee and returned to my bedroom. Curiosity led me to open it. I expected perhaps a restaurant photograph or something equally harmless.

An invoice appeared on my screen. The document was professionally designed and contained detailed information.

The header displayed bold professional lettering: Date Night Invoice – Amount Due: 1 Outstanding Balance.

Below this sat a complete breakdown of services provided with corresponding charges.

Initially, I assumed this was humor. Some strange comedy attempt that missed its mark. However, as I examined the contents, my morning coffee nearly made me sick.

The alleged services he had documented were completely absurd. They revealed his gentlemanly behavior in an entirely different perspective.

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

Engaging Conversation & Active Listening: A compliment about my looks

Full Dinner + Tip Covered: A second date, no excuses

The genuine shock came from the bottom section in bold lettering. This part confirmed his serious intent behind the invoice.

Payment is expected in full. No refunds. Failure to comply may result in an outstanding balance being sent to collections (Chris will hear about it).

Looking forward to your prompt payment!

Monetary compensation would have been offensive enough. However, demanding required affection and attention? What type of person behaves this way?

I captured the invoice immediately and forwarded it to Mia. Her reply came instantly.

“OH. MY. GOD. I’M SHOWING THIS TO CHRIS RIGHT NOW.”

“Is this actual reality???” I responded, remaining in shock. “He means this seriously!”

“Wait until Chris views this. He will LOSE IT,” she answered.

My phone rang five minutes later.

Chris called me, laughing uncontrollably.

“Kelly, this astounds me,” he gasped between breaths. “I have known this guy for years. I never imagined he would attempt something this crazy.”

“This is not a prank?” I questioned.

“Definitely not,” Chris verified. “Eric has always been somewhat… obsessive about dating. This exceeds all limits. We must retaliate against this person.”

Chris excelled at elaborate revenge schemes. Rather than simply mocking Eric in their group messages, he decided to escalate the situation.

“I will create a matching invoice,” he announced. “Identical format, false legal language, absurd fees, everything included.”

Chris delivered his masterpiece one hour later. He had itemized various charges for subjecting me to this ridiculous situation. The list made me laugh hysterically.

Service Invoice – Amount Due: A Lifetime of Silence

Introducing You to a Gorgeous Woman: 1 permanent block on all platforms

Letting You Sit at the Same Table as Her: A formal apology to all women you’ve dated before

Not Exposing You to the Entire Internet: A generous gift you should be grateful for

Payment is due IMMEDIATELY. Failure to comply may result in public humiliation. Cheers!

“This is brilliant,” I messaged him. “Deliver it!”

“Already sent!” He responded moments later.

Soon after, Eric sent me multiple furious messages.

“I simply wanted to establish reasonable expectations; wealth is not universal.”

“Chris behaves terribly as a friend.”

“You have lost an EXCELLENT man.”

I chose not to respond. What could I tell someone who believed human relationships operated like business deals? I sent him a thumbs-up symbol and blocked his contact information.

Mia contacted me that evening, still amused by the entire incident.

“I apologize sincerely,” she stated. “I genuinely believed he was reasonable. Chris had no knowledge of his true nature either.”

“Do not concern yourself,” I answered, surprised by my calm reaction. “At minimum, we all gained an entertaining tale.”

“Absolutely,” she concurred.

“This story will definitely be shared at every gathering for the following ten years.”

The entire situation taught me one important dating principle: When a man demands to cover the bill, confirm he will not mail you a bill later.

The keychain remained in my possession. I kept it not as a reminder of Eric, but as an amusing memento from the strangest date I ever experienced.

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