Man from Dating Site Brought His Parents on Our First Date with Their Ridiculous Demand – I Decided to Outplay Them

Who brings their parents to a first date? My boyfriend from a dating app did. But what really got me was the list of OUTRAGEOUS DEMANDS his parents brought with them. I knew I’d have to outwit them… but on my own terms.

When I virtually met Jacob on a dating site several months ago, we hit it off instantly. The connection felt real — the kind that makes your heart skip a beat when you see a new message notification. I grew to think that he was “the one,” but then when we actually met… well, let’s just say reality has a way of shattering our perfectly crafted illusions.

A woman holding a phone | Source: Unsplash

A woman holding a phone | Source: Unsplash

Three months of late-night texts and hour-long video calls had built up to this moment. Jacob wasn’t just another match; he was different.

While most guys led with cheesy pickup lines or bland “hey” messages, he had caught my attention with a detailed comment about my profile photo taken at Comic-Con.

“Is that a handmade Scarlet Witch costume?” he’d written. “The detail work is incredible!”

From there, our conversations flowed naturally. He listened, really listened, when I talked about my work as a graphic designer and my dreams of starting my own studio.

A woman using a computer | Source: Midjourney

A woman using a computer | Source: Midjourney

He shared my love for true crime podcasts and could quote every episode of my favorite shows by heart. When I mentioned my sister’s battle with depression, he opened up about his own experiences with anxiety.

“I feel like I can tell you anything,” he’d said during one of our video calls, his warm brown eyes crinkling at the corners. “I’ve never connected with someone like this before.”

“Me neither,” I’d admitted, feeling my cheeks flush. “Sometimes I worry this is too good to be true.”

He’d laughed then, running a hand through his dark hair. “I can’t wait to finally meet you in person. Friday at Coffee Beanz? 7 p.m.?”

A man using a laptop | Source: Pexels

A man using a laptop | Source: Pexels

“It’s a date! Finally!” I’d chirped, unable to contain my excitement.

“See you on Friday!” He said as I hung up, blushing.

I spent the entire week planning my outfit, finally settling on a gorgeous dress that my best friend Sarah insisted brought out my eyes.

“He won’t know what hit him,” she’d said, helping me style my hair.

Friday evening found me standing outside Coffee Beanz, smoothing down my dress for the hundredth time. Through the window, I could see couples enjoying their meals, soft candlelight flickering across their faces.

People in a cafe | Source: Unsplash

People in a cafe | Source: Unsplash

My hands were shaking slightly as I pushed open the heavy wooden door, the warm aroma of garlic and fresh bread enveloping me. My eyes nervously darted around in search of Jacob.

“Lia! Over here!”

I turned toward Jacob’s familiar voice, my practiced smile freezing on my face. There he sat, but not ALONE.

An older couple sat beside him, their faces beaming with smiles. My heart, which had been filled with excitement all day, sank to my stomach.

“Hey… um, hi, what’s going on?” I managed, my brain struggling to process the scene before me.

A shocked woman | Source: Pexels

A shocked woman | Source: Pexels

Jacob stood up, his bright smile unchanged as if this was completely normal. “Lia, I’m so excited to finally meet you! These are my parents, Linda and Patrick!”

Linda, a petite woman with perfectly coiffed gray hair and gold earrings that probably cost more than my monthly rent, gave me a practiced smile that didn’t reach her eyes. Patrick, sporting a dress shirt that seemed a size too small for his frame, barely looked up from his menu.

“Sit down, girl,” Linda patted the chair next to her, not next to Jacob. “While we wait for our appetizers, I have a few questions for you.”

An older lady smiling | Source: Midjourney

An older lady smiling | Source: Midjourney

I sank into the chair, still trying to make sense of this ambush. The waiter appeared with water glasses, and I found myself wishing it was something stronger.

That’s when Linda pulled out a crisp sheet of paper from her designer handbag.

“Now then,” she cleared her throat, clicking her gold-plated pen. “I’ve prepared a brief questionnaire to help us get to know you better. I want you to fill it out.”

Sheets of paper on a table | Source: Pexels

Sheets of paper on a table | Source: Pexels

My eyes scanned the paper she placed before me, each question worse than the last:

1. What is your current annual income and five-year career projection?

2. Please list any medical conditions, including a family history of genetic disorders.

3. How many romantic partners have you had, and what were the reasons for those relationships ending?

4. Do you own or lease your vehicle? What is your credit score?

5. Are you willing to sign a prenuptial agreement?

6. Do you plan to work after having children? If so, who will provide childcare?

7. What is your stance on living with in-laws?

8. Are you willing to host special occasions like Thanksgiving & Christmas every year without expecting a penny from your partner?

A startled woman covering her mouth | Source: Pexels

A startled woman covering her mouth | Source: Pexels

The questions went on and on like a never-ending train carriage. My water glass stopped halfway to my mouth. “I’m sorry, but is this for real?”

“Of course it is, dear,” Linda replied, her tone suggesting I was being deliberately difficult. “Our family has certain standards to maintain. We need to ensure any potential partners for our Jacob are… suitable.”

My eyes darted to Jacob, waiting for him to jump in, to say this was all a joke. But he just sat there, examining his napkin as if it held the secrets of the universe.

A man sitting casually | Source: Midjourney

A man sitting casually | Source: Midjourney

Something snapped inside me. Three months of building this connection, sharing hopes and fears, only to be treated like a job applicant? No. This called for a different approach.

“Would you excuse me for just a moment?” I smiled sweetly. “Ladies’ room.”

Instead of heading to the restroom, I ducked into the convenience store next door. Five minutes later, I returned with my own notebook and pen.

“Before I answer your questions,” I said, sitting down with renewed confidence, “I have a few of my own.”

A woman holding a piece of paper | Source: Pexels

A woman holding a piece of paper | Source: Pexels

Linda’s perfectly plucked eyebrows shot up in surprise as I placed the paper with my questions on the table. She picked it up and began reading loudly, her face speaking volumes of her anger.

“Question one: At what point did you realize your son wasn’t capable of choosing his own partner?”

Patricks’s face reddened. Jacob finally looked up from his napkin.

“Question two: How many women have actually completed your interrogation process? Or do most run screaming before the credit check?”

“This is completely inappropriate!” Linda’s voice pitched higher as she continued to read.

A furious older woman with a man | Source: Midjourney

A furious older woman with a man | Source: Midjourney

“Question three: Do you also inspect their teeth like show horses, or is that saved for the second date?”

“Question four: When Jacob moves out of your basement, will you be requiring his future wife to submit weekly progress reports?”

“Question five: Have you considered therapy for your control issues, or is that too personal a question?”

“That’s enough!” Jacob slammed his hand on the table, making the silverware jump. “You have no right to disrespect my family like this!”

An angry man | Source: Midjourney

An angry man | Source: Midjourney

I leaned back, crossing my arms. “Oh, but they have every right to treat me like I’m applying for a position at the FBI?”

“My parents are just looking out for me,” he protested, his voice weak. “They want what’s best— “

“No, Jacob. What’s best for you would be growing a backbone and living your own life.”

Linda and Patrick were already gathering their things, faces flushed with indignation. Linda’s hands shook as she stuffed her questionnaire back into her bag.

“We’re leaving,” she announced. “Jacob, come on. She’s not the one for you.”

“Wait!” I called out, loud enough for nearby tables to turn. “Aren’t you forgetting something?”

Side shot of a woman | Source: Midjourney

Side shot of a woman | Source: Midjourney

They paused. “WHAT??”

“Waiter, these people are trying to leave without paying their bill!” I announced loudly, waving to the waiter. “Guess running out on checks is another proud family tradition!”

The restaurant had gone quiet. Linda’s hands shook as she pulled out her credit card, practically throwing it at the waiter. I stood up, smoothing my dress once again.

“Well, this has been entertaining. I’ll cover my water.” I placed a five-dollar bill on the table and turned to Jacob.

“Good luck finding someone who meets your family’s rigorous standards. Although, you might want to try job recruitment sites instead of dating apps. I hear they provide detailed background checks and references.”

A woman laughing | Source: Midjourney

A woman laughing | Source: Midjourney

As I walked out into the cool evening air, my phone buzzed with a message from Jacob, “You didn’t have to be so cruel. My parents were just looking out for me.”

I typed back, “Just looking out for myself, mama’s boy. Goodbye!”

Later that night, Sarah called to hear about the date. After I finished telling her everything, she was quiet for a moment.

“You know what?” she finally said. “I bet Linda has a spreadsheet ranking all of Jacob’s potential wives.”

We both burst out laughing, and I felt the last of my disappointment melt away. Dodged a bullet? Absolutely. And I’ve never been so grateful for a red flag wrapped in a questionnaire.

A woman walking away | Source: Midjourney

A woman walking away | Source: Midjourney

This work is inspired by real events and people, but it has been fictionalized for creative purposes. Names, characters, and details have been changed to protect privacy and enhance the narrative. Any resemblance to actual persons, living or dead, or actual events is purely coincidental and not intended by the author.

The author and publisher make no claims to the accuracy of events or the portrayal of characters and are not liable for any misinterpretation. This story is provided “as is,” and any opinions expressed are those of the characters and do not reflect the views of the author or publisher.

While I was on vacation, my wealthy neighbor built a fence on my property, blocking my windows — I gave him the perfect lesson in return

After a week of sun and sand, Catherine was shocked to discover her new neighbor Jeffrey had built an imposing fence on her property. As a single mom, she couldn’t let this slide. What did she do to teach him a lesson he’d never forget?

Life as a single mom isn’t easy, but I’ve been making it work. I’m Catherine, 40 years old, and I’ve been raising my two boys, Liam (10) and Chris (8), all by myself for the past year.

Their father and I parted ways when I caught him cheating with another woman. Well, that’s a story for another time.

About two months ago, I bought a new house and moved in with my kids. It’s in a peaceful neighborhood with a beautiful forest nearby.

Everything about our new neighborhood seemed perfect until I met my next-door neighbor, Jeffrey. We had been at odds since the beginning.

I’ll never forget our first interaction.

It had been a day since we moved in when I heard a knock at my door. I opened it and saw him standing at my doorstep with a folder in his hand.

“Hello there, neighbor!” he said, extending his hand. “I’m Jeffrey. Welcome to the neighborhood!”

I shook his hand.

How nice! I thought. If only I knew what was coming in the days ahead.

“I wanted to discuss something important with you,” he continued, opening his folder.

“The previous owners signed this contract allowing me to build a fence on the property line.”

I raised an eyebrow. “Okay…?”

“So, I’ll be starting construction next week,” he said matter-of-factly.

I was stunned. “Excuse me? You’re not even asking for my permission?”

“Well, I have the contract right here—”

“That contract was with the previous owners,” I interrupted. “I’m the owner now, and I don’t want a fence blocking my view and sunlight.”

That’s when his face turned red.

“But I need this fence for privacy!” he yelled. “I’ve been planning this for months!”

“Why should I care about what the FORMER owner said?” I asked, but I never got a straight answer.

I just saw Jeffrey stomp out of my house.

Since that day, he’s been arguing with me almost every week about this fence. Apparently, he wants to host fancy garden parties without his guests seeing into my yard.

Well, excuse me for existing!

I couldn’t let him build that fence. I didn’t buy this house to stare at wooden planks instead of the beautiful sky and trees.

Little did I know, things were about to get much worse.

A few weeks ago, I decided to take my boys on a much-needed vacation. Liam and Chris were bouncing off the walls with excitement.

“Mom, can we go to the beach?” Liam asked.

Chris chimed in, “Yeah! And can we build a huge sandcastle?”

“Of course, boys!” I said as I hugged them. “We’ll do all that and more!”

We left for a week, looking forward to sun, sand, and relaxation. If only I’d known what was waiting for us when we got back.

As we pulled into our driveway, I noticed something odd. My heart sank as I realized what had happened.

“Boys, stay in the car for a minute,” I said as I got out.

My blood boiled with each step I took toward our house.

As I peeked to the right, I realized what had happened. There, right in front of our windows, stood a tall wooden fence. On our property. One foot from my windows!

“What the hell?!” I shouted, not caring who heard me.

Liam and Chris came running up behind me.

“Mom, what’s wrong?” Chris asked in a worried voice.

I took a deep breath. I had to stay calm for their sake. “Nothing, sweetie. Just a little… surprise from our neighbor.”

“But Mom,” Liam said, frowning, “we can’t see the trees anymore.”

My heart broke.

Jeffrey’s stupid fence had replaced the beautiful view from our windows that my boys loved so much. Now, we couldn’t even see the sky!

I couldn’t let this slide. I had to teach Jeffrey a lesson.

I had two options. Either take the legal route and wait for the authorities to take action or take matters into my own hands.

I chose the second one because my boys and I didn’t have enough time to take the legal route.

Later that night, I went to the pet store. I had a plan that I knew would work.

“Can I help you find anything?” the clerk asked.

I smiled sweetly. “Yes, I’m looking for an animal attractant spray. The strongest you have.”

After returning home, I waited until the neighborhood was asleep. Then, I went up to his precious fence and poured an entire bottle of the attractant liquid.

The pheromone scent was strong. It was designed to attract dogs for training purposes. But I had a feeling it might attract more than just dogs.

I did this for several nights in a row, ensuring the solution covered every inch of the fence.

Then, I waited.

It didn’t take long for results to show.

One night, as I was taking out the trash, I saw a stray dog lift its leg against the fence. I had to stifle a laugh.

“Good boy,” I whispered.

Over the next few days, more and more animals started visiting the fence. Foxes, raccoons, even a moose once! They all seemed to think Jeffrey’s fence was the perfect place to do their business.

I watched from my window as Jeffrey discovered the mess one morning. His face turned an impressive shade of purple as he realized what was happening.

But to my surprise, he didn’t take down the fence.

He started cleaning it.

Every morning, Jeffrey would come out with a bucket and scrub brush, muttering under his breath as he cleaned off the nightly deposits.

But no matter how much he cleaned, he couldn’t get rid of the pheromone scent. The animals kept coming back, night after night.

Soon, the smell became unbearable. Even my boys started to notice.

“Mom,” Chris said one day, holding his nose, “it stinks outside!”

Liam nodded in agreement. “Yeah, can we play inside today?”

“I know it smells bad, boys,” I said. “Just give it a few more days, okay?”

They nodded, but I could see they were disappointed. I hoped my plan would work soon.

The next day, I was coming back from a grocery run when I saw one of our other neighbors, Mrs. Thompson, knocking on Jeffrey’s door.

I slowed down, pretending to check my mail as I eavesdropped.

“Jeffrey,” Mrs. Thompson began, “what on earth is that smell coming from your yard? It’s awful!”

Jeffrey seemed so embarrassed.

“I… I’m working on it, Mrs. Thompson. There’s been a bit of an animal problem.”

“Well, work faster!” she snapped. “It’s affecting the whole neighborhood!”

As Mrs. Thompson stormed off, Jeffrey caught my eye. He had this apologetic look on his face that I had never seen before. I smiled at him and quickly walked into my house.

That evening, I watched from my other window as Jeffrey attacked the fence with every cleaning product known to man.

He scrubbed and sprayed for hours, but the smell lingered. Finally, he threw down his brush in defeat and trudged back to his house.

The next morning, I was awakened by a loud noise outside. I peeked through my curtains and had to blink a few times to make sure I wasn’t dreaming.

I could see Jeffrey overseeing a team of workers as they took down the fence.

I couldn’t believe my plan had actually worked!

I woke up the boys with the good news. “Liam! Chris! Come look outside!”

They raced to the window, their eyes widening as they saw the fence coming down.

“Mom, we can see the trees again!” Chris exclaimed.

Liam hugged me tight. “You’re the best, Mom!”

And with that, our view was restored, and Jeffrey had learned his lesson. However, the story doesn’t end there.

Later that day, Jeffrey approached me while I was gardening in the front yard.

“Catherine,” he started, clearing his throat, “I, uh… I want to apologize.”

“Oh?” I pretended to act surprised.

He nodded. “I shouldn’t have put up that fence without your permission. It was wrong of me.”

“Yes, it was,” I agreed, crossing my arms.

“I’ve learned my lesson,” he continued. “From now on, I’ll respect your property and your rights as a neighbor.”

“Apology accepted, Jeffrey,” I smiled. “Let’s start over, shall we?”

“I’d like that.”

As Jeffrey walked away, I couldn’t help but feel proud. I had stood up for myself and my boys, and in the end, everything worked out.

That incident taught me that life sometimes puts you in situations where you have to get creative to find a solution, just like I had to come up with a plan to teach Jeffrey a lesson he’ll never forget.

Do you think I did the right thing?

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