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.

Man on the Street Offered Me Either 2 Days’ Pay for Doing Nothing or a Full-Time Job – If Only I’d Known How It Would End

I was struggling to help Mom pay my late father’s medical debts when a stranger running a social experiment threw me a lifeline: quick cash or a job. I took the job, but after weeks of hard labor, I discovered the stranger hadn’t been entirely honest with me.

The day Jeremy approached me in that dingy coffee shop, I was running on three hours of sleep and enough caffeine to power a small city. Dad’s medical bills were still coming in, each one a fresh reminder of everything we’d lost.

An exhausted man in a coffee shop | Source: Midjourney

An exhausted man in a coffee shop | Source: Midjourney

Mom was getting worse. She wasn’t sick exactly, but that bone-deep sadness that comes from losing your other half was taking a heavy toll. I’d moved across the country to help her, but on some days, it felt like we were drowning.

I’d been applying for jobs non-stop and heard every rejection in the book, from nicely worded emails to rude, in-your-face dismissals.

I was getting desperate and even considered doing something stupid when a stranger slid into the seat across from me.

A man pulling out a chair | Source: Midjourney

A man pulling out a chair | Source: Midjourney

“Interesting choice of drink,” the stranger said, nodding at my espresso.

I was about to tell him to pick one of Pittsburgh’s many bridges to jump off, but something stopped me. I’m not sure if it was his kind eyes or genuine smile, but I decided to find out what he wanted.

I wrapped my hands tighter around the warm cup. “Can I help you?”

“Actually, I’m hoping I can help you,” he replied.

A man in a coffee shop | Source: Midjourney

A man in a coffee shop | Source: Midjourney

“My name’s Jeremy,” he said, folding his hands on the table. “I’m running a social experiment. Here’s the deal: I can give you two days’ salary right now, no strings attached. Or…” He leaned forward slightly. “I can give you a full-time job. It’ll be tough, but the end payout—”

“The job,” I said before he could finish. “I’ll take the job.”

Jeremy’s eyebrows lifted slightly. “Don’t you want to hear the amounts?”

A man arching his eyebrows | Source: Midjourney

A man arching his eyebrows | Source: Midjourney

I thought about Mom’s face when another bill arrived that morning, how her hands shook as she added it to the growing pile.

“Doesn’t matter. I need real work, not handouts.”

“Well, if you’re certain…” he reached into his messenger bag and pulled out a thin stack of paper. “Here’s your contract. Sign it, and report for work tomorrow at this address.”

He slid a slip of paper across the table with an address on it as I signed the contract.

A person signing a contract | Source: Pexels

A person signing a contract | Source: Pexels

It seemed like a standard work contract with a few extra details pertaining to the experiment. I was so relieved to finally have a job I didn’t bother reading the fine print.

Rookie mistake.

The next morning, I realized exactly what I’d signed up for. The address Jermey provided led me to a construction site for some housing project. Several homes were almost finished, but others were just foundations in the dirt.

A housing construction site | Source: Pexels

A housing construction site | Source: Pexels

The place was filled with dust and noise and men who looked like they bench-pressed trucks for fun. The foreman, Mike, handed me a hard hat with a grunt.

“You ever done this kind of work before?” he asked.

“No, but I learn fast.”

He snorted. “We’ll see about that.”

The first week nearly broke me.

A man working on a construction site | Source: Midjourney

A man working on a construction site | Source: Midjourney

My muscles screamed, my hands blistered and split, and the summer heat was relentless. But every night, when I dragged myself back to Mom’s apartment, she’d look at me with such worry that I’d force a smile.

“I’m fine, Mom,” I’d say, hiding my raw palms. “Just getting stronger.”

“Your father would be so proud of you,” she’d whisper, and those words became my armor.

A woman smiling sadly | Source: Midjourney

A woman smiling sadly | Source: Midjourney

It all seemed worth it when I met up with Jeremy again, and he gave me my first paycheck.

“This is for your first week of work,” he said. “As stated in the contract, you receive wages for your first week and the balance will be paid at the end of the month.”

“Thank you,” I said, almost in tears as I clutched the paper. It wasn’t much, but I was grateful for every penny.

By the second week, I’d fallen into a rhythm.

A determined man | Source: Midjourney

A determined man | Source: Midjourney

I’d wake up before dawn, gulp down coffee, and get to the site early. The work was still brutal, but I was learning and getting stronger. One of the older workers, Carl, took me under his wing, showing me how to properly handle tools and read blueprints.

“You’ve got good instincts,” he said one morning, watching me lay brick. “Reminds me of my daughter. She’s in engineering now.”

“What made her choose that?”

A man laying bricks | Source: Midjourney

A man laying bricks | Source: Midjourney

Carl smiled, the wrinkles around his eyes deepening. “Watching me work all those years. Said if I could build houses, she could design them.”

Jeremy would show up periodically, clipboard in hand, watching from a distance. Sometimes, he’d join me during lunch breaks, asking questions about my life while I wolfed down sandwiches.

“Tell me about your dad,” he said one day, three weeks in.

Two men speaking over lunch | Source: Midjourney

Two men speaking over lunch | Source: Midjourney

I paused mid-bite. “He was the kind of person who’d give you his last dollar if you needed it. Cancer took him fast — six months from diagnosis to…” I couldn’t finish the sentence. “The medical bills took everything else.”

Jeremy nodded, making another note. “And yet here you are, still fighting.”

“What choice do I have?”

That evening, Mom was having one of her bad days. I found her sitting in Dad’s old chair, clutching his worn flannel shirt.

A grieving woman | Source: Midjourney

A grieving woman | Source: Midjourney

“I keep thinking I hear him in the kitchen,” she said quietly. “Making his terrible coffee.”

I sat at her feet like I used to as a kid. “Remember how he’d drink it straight from the pot sometimes?”

She laughed softly. “Said cups were just extra dishes to wash.” Her hand found my shoulder. “You’re so much like him, sweetie. Same stubborn streak.”

The work got harder as we went along.

A man working on a construction site | Source: Midjourney

A man working on a construction site | Source: Midjourney

I learned to lay bricks, install windows, and paint walls. The other workers slowly warmed up to me, especially after I stayed late one evening to help Mike finish a difficult section of roofing.

“You’re not half bad, kid,” he said, which from him felt like a Nobel Prize.

“Coming from you, Mike, that’s practically an award.”

He barked out a laugh. “Don’t get cocky. You’ve still got a lot to learn.”

A laughing construction worker | Source: Midjourney

A laughing construction worker | Source: Midjourney

But I was learning faster than anyone expected.

Each day brought new challenges: measuring twice and cutting once, ensuring level surfaces, and matching paint colors perfectly. I threw myself into every task, trying to lose myself in the work so I wouldn’t have to think about the empty chair at home or Mom’s quiet crying at night.

Then came the day everything fell apart.

A serious man | Source: Midjourney

A serious man | Source: Midjourney

I’d completed four weeks of backbreaking work when Jeremy showed up looking grim. He pulled out the contract, pointing to fine print I’d never noticed.

“Due to certain conditions not being met,” he began, “you won’t receive the final payment—”

“No.” The word came out like a punch. “No, you can’t do this. I worked myself half to death. I trusted you!”

“Eric—”

A man holding documents | Source: Midjourney

A man holding documents | Source: Midjourney

“I needed that money! My mom — we’re about to lose everything, and you…” My voice cracked, and I hated myself for it.

Jeremy reached into his briefcase and pulled out a small box. “Open it.”

“I don’t want your consolation prize.”

“Eric. Open the box.”

Inside was a single key, new and gleaming. I stared at it, uncomprehending.

A key in a gift box | Source: Midjourney

A key in a gift box | Source: Midjourney

“This house,” Jeremy said softly, “the one you helped build? It’s yours.”

I thought I’d misheard him. “What?”

He pulled out another set of papers — a deed. I realized with growing shock that it had my name on it.

“The experiment wasn’t about the work. It was about finding someone who deserved this. Someone who would choose the harder path, who would give everything they had for the people they love.”

A smiling man holding documents | Source: Midjourney

A smiling man holding documents | Source: Midjourney

My legs gave out, and I sat hard on the ground. “I don’t understand.”

“You built your own home, Eric. Every brick, every nail. You put your heart into it without even knowing. And now it’s yours, free and clear.”

I ran home faster than I’d ever moved in my life. Mom was in her usual spot by the window, staring at Dad’s old gardening tools.

“Mom,” I gasped out. “Mom, you’re not going to believe this.”

A happy man | Source: Midjourney

A happy man | Source: Midjourney

When I finished telling her, we both broke down. She pulled me close, and for the first time since Dad died, her embrace felt strong again.

A month later, we stood in our new living room. Sunlight streamed through the windows I’d installed, catching the paint I’d carefully applied to the walls. Mom was already planning where Dad’s old armchair would go and talking about planting a garden in the spring.

“He would have loved this place,” she said, touching the wall gently. “Remember how he always wanted to build his own house?”

A happy woman in a new house | Source: Midjourney

A happy woman in a new house | Source: Midjourney

I looked around at the house I’d built with my own hands.

In every corner, I could see traces of the lessons I’d learned: Carl’s patient instruction in the perfectly aligned bricks, Mike’s demanding standards in the precise angles of each joint, and my determination in every detail I’d insisted on getting just right.

“Yeah,” I said, smiling through tears. “He really would have loved this.”

A happy man | Source: Midjourney

A happy man | Source: Midjourney

And somewhere, I hoped, he was watching, proud of the story we were about to begin.

Here’s another story: When Belinda jokes about skipping her SIL’s strict vegetarian Thanksgiving, her husband Jeremy’s reaction is anything but funny. His sudden anger and ultimatum for divorce leave her reeling. As tensions rise, Belinda uncovers secrets that hint at a far deeper betrayal hidden in plain sight.

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.

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