My Date Insisted on Paying the Bill – I Wish I Hadn’t Let Him
When Eric insisted on paying for our first date, I thought I’d met a true gentleman. Roses, a sweet gift, charming conversation — he was checking all the boxes. When he texted me the next day, I expected a cute follow-up, but my stomach dropped when I read his message.
My best friend, Mia, meant well when she offered to set me up on a date, but her skills as a matchmaker were completely untested.
A woman in her bedroom | Source: Midjourney
“He’s super nice, Kelly! Total gentleman. You’ll love him,” Mia insisted over the phone while I rummaged through my closet.
“You’ve never set me up before,” I reminded her. “What makes you think you know my type?”
“Because I know you better than anyone,” she replied confidently. “Plus, Chris vouches for him too. They’ve been friends for ages.”
A woman in a walk-in closet | Source: Midjourney
That gave me pause. Chris, Mia’s boyfriend, was a pretty good judge of character. If he thought this Eric guy was decent, maybe there was hope.
“Fine,” I sighed. “Show me a picture at least.”
A moment later, my phone pinged with an incoming message.
A cell phone | Source: Pexels
The guy in the photo wasn’t bad looking: clean-cut, well-dressed, with a warm smile that reached his eyes.
“Okay, he’s cute,” I admitted.
“Told you!” Mia squealed. “Text him and set it up. You won’t regret it, I promise.”
After a few casual texts, I agreed to meet Eric for dinner at a new Italian place with a great view of the river. Nothing too fancy, but nice enough for a first date.
A charming restaurant | Source: Pexels
I arrived five minutes early and waited near the entrance, like we’d agreed. I was nervously checking my appearance with my phone camera when I spotted him approaching the restaurant.
My pulse quickened a little. The photo hadn’t lied — he was attractive in that clean-cut, business-casual way, and he carried himself with confidence.
What I hadn’t expected was the bouquet of roses in his hand.
A man holding a bouquet of roses | Source: Midjourney
Not cheap grocery store flowers, but an actual professional arrangement tied with a ribbon.
“You must be Kelly,” he said, flashing that same warm smile from his photo. “These are for you.”
“Wow, thank you,” I replied, genuinely surprised as I accepted them. “You didn’t have to do that.”
A smiling woman holding a bouquet | Source: Midjourney
“Figured I’d start the night off right,” he said, handing me the flowers.
But that wasn’t all.
He reached into his jacket pocket and pulled out a small gift box tied with a cyan bow.
A wrapped gift box tied with a bow | Source: Pexels
“What’s this?” I asked, my eyebrows shooting up in surprise.
“Just a little something. Open it,” he encouraged.
Inside was a sleek silver keychain with the letter “K” engraved on it. It was tasteful and personalized, something that required thought.
A silver keychain in a gift box | Source: Gemini
“Something just for you,” he said smoothly. “I asked Mia what you might like.”
I was honestly impressed. Flowers and a thoughtful gift on a first date? This man was clearly making a statement. Either he was seriously interested, or he was the king of first impressions.
“This is really nice of you,” I said, genuinely touched. “Thank you.”
A woman holding a bouquet smiling at someone | Source: Midjourney
Eric continued his gentlemanly routine without missing a beat. He opened the door, pulled out my chair, and maintained steady eye contact throughout our conversation.
He asked thoughtful questions about my job as a graphic designer, remembered details about my family that I’d only mentioned in passing during our texts, and made me feel like the most interesting person in the room.
“So what made you agree to this setup?” he asked after we’d ordered our meals.
A man in a restaurant smiling at his date | Source: Midjourney
“Mia can be very persuasive,” I laughed. “Plus, she and Chris both vouched for you, which rarely happens.”
“They’re a great couple,” he nodded. “Chris and I go way back to college. He’s always been a stand-up guy.”
The conversation flowed naturally from there.
Two people in a restaurant | Source: Midjourney
We discovered shared interests in true crime podcasts and documentaries about strange subcultures.
He told amusing stories about his job as a marketing manager, and I caught myself thinking this might be the best first date I’d ever had.
When the check came, I reached for my purse.
A woman holding a purse | Source: Pexels
“Absolutely not,” Eric said firmly, putting his card down on the check presenter before I could even open my purse. “A man pays on the first date.”
His tone surprised me a little. It wasn’t just polite, but final, almost like he was reciting an unbreakable rule.
I paused for half a second, then shrugged. “Okay, if you insist. Thank you.”
A woman smiling at someone | Source: Midjourney
I wasn’t about to argue over a free meal, especially after such a pleasant evening. We walked out together, and he asked if he could call me again soon.
“I’d like that,” I replied, and meant it.
He hugged me goodbye (a perfect balance of friendly and interested without being creepy). I drove home with a smile on my face thinking that was one of the most amazing first dates I’d ever been on.
Evening traffic in a city | Source: Pexels
The next morning, I woke up to a notification from Eric. My sleepy brain expected a cute “had a great time” text, but instead, I saw an attachment.
I made coffee and then returned to bed. Curious, I opened it, expecting maybe a photo from the restaurant or something similarly innocuous.
It was an invoice. A professionally formatted, detailed invoice.
A woman in bed looking at her phone | Source: Midjourney
At the top, in bold professional font:
Date Night Invoice – Amount Due: 1 Outstanding Balance.
Underneath that was a full breakdown of services rendered with attached charges.
At first, I thought it was a joke; some weird attempt at humor that wasn’t quite landing. But as I read through it, my morning coffee nearly came back up.
A woman holding a mug | Source: Midjourney
The so-called services he’d listed were utterly ridiculous and made me see his gentlemanly charm in a whole new light.
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
Engaging Conversation & Active Listening: A compliment about my looks
Full Dinner + Tip Covered: A second date, no excuses
A woman staring at her phone uncertainly | Source: Midjourney
But the real kicker, the bit that made me realize he’d sent this invoice in earnest, appeared at the bottom in bold text.
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!
My jaw hit the floor.
A woman staring at her phone in shock | Source: Midjourney
It would’ve been bad enough if he’d expected monetary compensation, but charging me with required affection and attention? Who does that?
I screenshot the invoice immediately and sent it to Mia. Her response was instant.
“OH. MY. GOD. I’M SHOWING THIS TO CHRIS RIGHT NOW.”
A woman using her cell phone | Source: Midjourney
“Is this real life???” I typed back, still in disbelief. “He’s serious about this!”
“Wait till Chris sees this. He’s going to LOSE IT,” she replied.
Five minutes later, my phone rang.
A woman answering a phone call | Source: Midjourney
It was Chris, and he was howling with laughter.
“Kelly, I can’t believe this,” he managed between gasps. “I’ve known this dude for years and never, not once, did I think he’d pull something this insane.”
“So, this isn’t a joke?” I asked.
A woman speaking on her cell phone | Source: Midjourney
“No way,” Chris confirmed. “Eric’s always been a bit… intense about dating, but this is next level. Okay, we need to get back at this dude.”
Chris was the mastermind of next-level pettiness.
Instead of just roasting Eric in their group chat, he planned to take it up a notch.
A woman on a phone call | Source: Midjourney
“I’m making an identical invoice,” he declared. “Same formatting, fake legal tone, ridiculous charges, the works.”
An hour later, Chris sent me his creation.
In it, he’d listed a series of charges for putting me through this nonsense that left me in stitches.
A woman laughing hard | Source: Midjourney
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: A deep, personal reflection on why you’re single
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!
A woman smirking | Source: Midjourney
“This is perfect,” I texted him. “Send it!”
“Forwarded!” He replied a moment later.
Not long afterward, my phone lit up with a series of increasingly angry messages from Eric.
A cell phone on a table | Source: Pexels
“Wow, really mature.”
“I was just trying to set realistic expectations; not everyone is rich.”
“Chris is a terrible friend.”
“You just missed out on a GREAT guy.”
I didn’t bother engaging. What was there to say to someone who thought human connection worked on a transaction basis? I just sent him a thumbs-up emoji and blocked his number.
A woman using a cell phone | Source: Pexels
Mia called me later that night, still laughing about the whole situation.
“I’m so sorry,” she said. “I really thought he was normal. Chris had no idea he was like this either.”
“Don’t worry about it,” I replied, surprising myself with how unbothered I felt. “We all got a great story out of it, at least.”
“True,” she agreed. “This is officially going to be told at every party for the next decade.”
A woman laughing | Source: Midjourney
