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What Happened When I Let My Date Cover the Bill

Posted on August 8, 2025

I wish I hadn’t let my date pay for the meal.

I believed I had found a terrific guy when Eric insisted on paying for our first date. He was addressing all of her wants with flowers, a wonderful present, and a charming talk. I thought it would be good to hear from him the next day, but what he said made me sick.

 

 

 

Mia, my best friend, offered to set me up on a date with the best of intentions, but she had never done it before.

“Kelly, he’s a really nice guy!” A real gentleman. Mia called me as I was going through my clothes and said, “You’ll love him.”

 

 

 

 

Telling her, “You haven’t set me up before,” “How do you know who I am?”

She said with certainty, “Because I know you better than anyone else.” Chris is also on his side. They’ve known each other for a long time.

That made me think. Chris, Mia’s boyfriend, was pretty excellent at figuring people out. There might be hope if he felt this Eric person was great.

“Okay,” I responded with a yawn. “Just show me a picture.”

 

 

 

 

My phone rang a few seconds later to tell me I had a new message.

The guy in the picture was attractive. He was well-groomed, clean-cut, and had a terrific smile that reached his eyes.

I said, “Okay, he’s cute.”

“Look! I told you so! Mia yelled. “Set it up and text him.” I promise you won’t be sorry.

After jokingly texting back and forth, I decided to have dinner with Eric at a new Italian restaurant with a fantastic view of the river. It’s fine for a first date, but it’s not anything special.

 

 

 

As we had planned, I got there five minutes early and waited by the door. I was nervously using my phone’s camera to see how I looked when I noticed him walking toward the restaurant.

My heart rate went up a little. He looked excellent in that polished, business-casual style, and the photo suggested that he was confident.

I was shocked to see the roses he was holding.

Not flowers from the store, but a real, professional arrangement with a bow on it.

He grinned a lot as he did in the picture and added, “You must be Kelly.” “These are for you.”

“Wow, thank you,” I said, totally startled that they were offering things to me. “You didn’t need to do that.”

When he gave me the flowers, he said, “I thought I’d start the night off right.”

But that wasn’t all.

 

 

 

 

He pulled a small box with a blue bow out of his jacket pocket.

“What is this?” When I asked, I was astonished and raised my eyebrows.

“Just a little bit.” He pushed, “Open it.”

There was a smooth silver keychain inside with the letter “K” on it. It was one of a kind and fashionable, which was something to ponder about.

Without a hitch, He said, “Something just for you.” “I asked Mia what you might want.”

I have to say, I was shocked. A first date with flowers and a nice gift? It was obvious that this man had something to say. He was either genuinely interested or really excellent at making first impressions.

When I said, “This is really nice of you,” I was very moved. “Thanks.”

Eric’s charming routine didn’t lose a beat. He opened the door, pulled out my chair, and kept looking at me while we talked.

He made me feel like the most intriguing person in the room, recalled facts about my family that I had just mentioned in passing in our discussions, and asked great questions about my profession as a graphic designer.

 

 

 

 

He inquired, “What made you agree to this arrangement?” after we had ordered lunch.

I laughed and said, “Mia can be very convincing.” “Plus, both she and Chris said good things about you, which doesn’t happen very often.”

He nodded and said, “They’re a great couple.” “I’ve known Chris since college.” He has always been honest about what he thinks.

After that, the conversation got bigger.

We both liked podcasts and films about real crimes and weird subcultures.

He told humorous anecdotes about his profession as a marketing manager, and I couldn’t help but think that this could be the best first date I’ve ever had.

 

 

I took my handbag when the check came.

Eric answered firmly, “No way,” and slapped his card on the check presenter before I could even get my wallet out. “On the first date, a man pays.”

I was a little astonished by the way he spoke. He sounded like he was reading an unbreakable law, and it wasn’t just nice; it was the end.

After waiting for half a second, I shrugged. “Okay, if that’s what you want.” Thank you.

 

 

 

 

I didn’t want to fight over a free dinner, especially after such a nice night. He wanted to know if he could call me again soon after we said goodbye.

I actually meant it when I said, “I’d like that.”

He hugged me goodbye in a way that was kind and interested, but not weird. I felt it was one of the finest first dates I’d ever been on, and I smiled the whole way home.

Eric texted me the next morning. I didn’t get the charming “had a great time” text that my groggy head was expecting. Instead, I noticed an attachment.

After I made coffee, I went back to bed. I opened it because I was interested and assumed it might be a photo of a restaurant or anything like that.

It was a bill. An invoice that is exceedingly clear and well-organized.

In a bold, businesslike font above:

There is still one balance outstanding on the Date Night Invoice.

 

 

 

 

Below that, there was a full list of the services available and their prices.

I believed it was a joke that wasn’t working out at first. But when I read it, I almost had my morning coffee again.

I saw his gentlemanly charm in a whole new light after I saw how stupid the “services” he had bragged about were.

1 hug for the arrangement of roses

A personalized keychain and a coffee date (must be booked within a week) as a gift

Taking a picture of each other while you open the car door

Taking the chair out: Keeping hands for the date that is coming up

 

 

Active Listening and Talking to Each Other: Someone remarked something about how I looked.

Dinner was nice, and the advice was to not make up reasons for a second date.

At the bottom, there was bolded wording that displayed the actual kicker—the part that made me think he really sent this bill.

You must pay in full. There are no refunds. If Chris doesn’t pay a debt, it will go to collectors, and he will be warned about it.

We look forward to getting your payment on schedule!

My lips fell to the ground.

 

 

 

 

It would have been awful enough if he had begged for money, but to charge me for the love and care I needed? Who does that?

I quickly forwarded Mia a screenshot of the bill. She responded right away.

“Oh my God. Right now, I’m showing this to Chris.

“Is this real life?” I typed back, still in shock. “He means it!”

“Hold on for Chris’s answer to this. “He’s going to LOSE IT,” she said.

Five minutes later, my phone rang.

Chris was there, and he couldn’t stop laughing.

In between gasps, he was able to shout, “Kelly, I can’t believe this.” “I’ve known this guy for a long time, and I never thought he would do something this crazy.”

“So, this isn’t a joke?” I asked.

 

 

 

 

Chris said, “No way.” “Eric’s dating has always been a little… intense, but this is really intense.” We need to get back at this guy.

Chris was the most petty person ever.

He wanted to do more than just poke fun of Eric in their group chat.

He said, “I’m writing an invoice that looks just like this one.” “Same format, fake legal tone, crazy fees, the whole thing.”

Chris sent me his work an hour later.

He had charged me a lot for putting me through this stupidity, which made me laugh out loud.

The price for the service states you owe a lifetime of silence.

There is a lovely lady here to see you: One permanent block on every platform

A deep, intimate look at why you’re single: Convincing Her That You Were a Gentleman

 

 

 

 

An official apology to all the ladies you’ve dated for letting you sit at the same table as her

Not letting you see the complete web: A good gift that you should be thankful for

You have to pay RIGHT NOW. If you don’t follow the guidelines, you can be embarrassed in public. Cheers!

I wrote him an email that stated, “This is perfect,” and “Send it!”

“Sent!” After a time, he eventually answered.

Soon after, my phone got a slew of messages from Eric that got angrier and angrier.

“Wow, that’s very mature.”

“Not everyone is rich; I was just trying to be honest.”

“Chris isn’t a good friend.”

“You just missed a great guy.”

 

 

 

 

I didn’t even try to chat to them. What would you say to someone who thought that commercial dealings were the basis of relationships? I texted him a thumbs-up emoji and blocked his number.

Mia called me later that night and was still giggling over what had happened.

“I really thought he was normal,” she said. “I’m really sorry.” Chris didn’t know what kind of person he was either.

I told them not to worry about it, and I was amazed at how calm I felt. At least we all got a good story out of it.

“That’s right,” she said. “This is going to be the talk of every party for the next ten years.”

 

 

 

 

One thing I learnt about dating from all of this is that if a man insists on paying, you should make sure he won’t send you a bill later.

But what about the keychain? I held on to it. Not because it made me think of Eric, but it was a funny reminder of the craziest date I’ve ever been on.

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