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.

Disguised as a Cleaner, a Journalist Faces the Unexpected When a Millionaire Recognizes Her Pendant – Story of the Day

Laura believed that her writing could change the world. But reality turned out differently, and her boss pushed her to dig up dirt on famous people. Desperate to save her job, she disguises herself as a cleaner to get compromising details on a millionaire. However, she uncovers a life-changing truth in the process.

The office hummed with the familiar sounds of keyboards clicking, phones ringing, and the occasional burst of laughter from a distant corner.

Laura sat at her desk, papers scattered around her, but her focus was elsewhere.

Her thoughts were interrupted when Reggie, the editor-in-chief, stepped out of his office.

His eyes scanned the room until they landed on her. He looked tired—more tired than usual—and his face carried the weight of disappointment.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“Laura… come to my office for a minute,” he said. His tone was calm but firm. He held the door open, waiting for her to follow.

Taking a deep breath, Laura rose from her chair and walked toward Reggie’s office, each step feeling heavier than the last.

“Sit down,” Reggie said, gesturing to the chair across from his desk.

“Reggie, I was just about to tell you about a new article I’m working on,” she began, trying to sound upbeat. “It’s about the chemical pollution in a nearby lake—”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“That’s exactly what I wanted to discuss with you,” Reggie cut in, sighing as he sank into his chair. He folded his hands and looked directly at her.

“Laura, pollution in forests, lakes, the extinction of… what are they called again?”

“California condors,” Laura said, her tone sharp.

“Condors, yes.” He nodded.

“People don’t care about this stuff, Laura. They don’t read it. And it’s not just my opinion—the data backs it up.”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Laura’s brow furrowed. “But people should care, Reggie! This isn’t just about nature; it affects our health, our communities—everything!”

Reggie leaned forward, his voice hardening.

“It doesn’t bring in money. We all need to eat. Salaries need to be paid, and I can’t pay someone who isn’t generating revenue.”

Reggie softened his tone, removing his glasses and rubbing his temples.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“I like you, Laura. You’re talented, and you care about your work. That’s why I’m trying to help you.”

“How?”

Reggie slid a photograph across the desk. It showed an elderly man with a stern expression.

“This is Mr. Weiss,” Reggie said. “You know who he is, don’t you?”

“A wealthy man,” Laura murmured, studying the image.

“The wealthiest man in the city,” Reggie corrected.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“Rumor has it he’s been spending tens of thousands on private investigators. Years of it.”

“And?” Laura asked, confused. “It’s his money. Why does that matter?”

“Why would an old man need private investigators?” Reggie leaned back, a sly smile forming.

“Mistresses, scandals, maybe even crimes. Find anything—and I mean anything—about his expenditures, and spin it into a story. This could be the article that saves your career.”

Laura hesitated. “And if I can’t?”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Reggie’s smile faded. “Then I’d recommend you start looking for another job.”

The cold air nipped at Laura’s cheeks as she stood in front of the grand estate, its towering gates and sprawling lawn exuding wealth and history.

Taking a deep breath, she straightened her shoulders and rang the doorbell.

The heavy wooden door creaked open slowly, revealing an elderly man. His figure was slightly hunched, his face marked by deep lines of exhaustion.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Dark circles framed his eyes, and his scruffy beard looked like it hadn’t been groomed in days.

“Good morning, Mr. Weiss,” Laura said with a polite smile that she hoped masked her nerves.

“My name is Laura. We spoke on the phone about the cleaning position.”

“Good morning,” Mr. Weiss replied, his voice quiet and tinged with weariness. “Come in. Forgive the mess; there’s plenty of work to keep you busy.”

Laura stepped inside, her eyes widening as she took in the space.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

A thick layer of dust covered the once-pristine surfaces, cobwebs adorned the corners, and books and papers were scattered haphazardly across the rooms.

“As you can see,” Mr. Weiss continued, “I really need the help. Start wherever you’d like. I’ll be in my study.”

With that, he turned and shuffled away, closing the study door behind him.

“Thank you for the opportunity, Mr. Weiss,” Laura called after him, but he didn’t respond.

Through the brief crack before the door shut, Laura glimpsed his desk. It was cluttered with papers, photographs, and what looked like old receipts.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Her heart raced—this could be where the secrets were buried.

Laura spent the next hour cleaning the house, her movements mechanical as her mind churned with plans.

Finally, she approached the study door and knocked softly. “Mr. Weiss, I’m coming in to clean—”

“No!” His voice was startlingly sharp as the door opened just enough for him to peer out.

“The study doesn’t need cleaning. Thank you for your work today. If you’ve finished the other rooms, you’re free to leave.”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“There are still a couple of rooms left,” Laura replied, feigning disappointment, but her mind was already racing.

The study was off-limits, and she was more determined than ever to find out why.

Laura crouched near the sofa, her heart racing.

She glanced toward the study door, still closed, as her mind raced through the plan one more time.

It wasn’t elegant, but it might work. Taking a deep breath, she screamed, her voice sharp and filled with faux terror.

“Aaaaah! Mr. Weiss! Help!”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

The sound of hurried footsteps echoed down the hallway. Moments later, Mr. Weiss appeared, his face a mask of alarm.

“What happened?” he demanded, clutching the edge of the doorway.

“There’s a rat!” Laura cried, pointing under the couch with a trembling hand. “It just ran under there! Please, I can’t stand rats—they terrify me!”

“A rat?” Mr. Weiss frowned, his brow furrowing.

“That’s impossible.” He grabbed a broom leaning against the wall and knelt to peer under the couch.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“Where? I don’t see anything. Did it run out?” he asked, poking around with the broom handle.

“I… I don’t know!” Laura stammered, backing toward the hallway. “Just keep looking. I’ll hide in the kitchen!”

Mr. Weiss grumbled but continued his search, muttering to himself about how unlikely it was.

As soon as he was fully distracted, Laura moved quickly. She slipped into his study, closing the door as quietly as possible.

The room was dim, illuminated only by a small desk lamp. Papers were strewn across the desk—receipts, handwritten notes, and photographs.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Laura’s journalist instincts kicked in as she pulled a small camera from her pocket and took pictures.

Her hands trembled as she worked quickly, her breath shallow.

Then she saw it. Among the scattered documents was a detailed sketch of a medallion.

She froze, her pulse hammering in her ears.

Reaching for her necklace, she pulled the small pendant from under her blouse and held it next to the sketch. They were identical.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“Laura.”

The low, heavy voice sent a chill down her spine. She turned to see Mr. Weiss standing in the doorway, his face shadowed.

“I told you not to come in here,” he said, his voice filled with a mix of anger and pain.

Her hand instinctively clutched the pendant. Mr. Weiss’s eyes widened as he stepped closer, his gaze fixed on the pendant.

“Where did you get that pendant?” he asked, his voice trembling. He reached out, his hand shaking as he touched the necklace.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“Tell me! Where?”

“It was my mother’s,” Laura snapped, pulling back.

“Your mother…” Mr. Weiss whispered, his face pale. “Was her name Dora?”

Laura’s breath caught. “Yes. How do you know that?”

Mr. Weiss’s knees buckled, and he sank to the floor. Tears welled in his eyes as his voice broke.

“Dora… my sweet Dora. She had a daughter…” He looked up at Laura, his expression filled with anguish. “Forgive me. Please forgive me.”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Laura staggered back, her hand gripping the desk for support. “You knew my mother?”

“I’m your father,” Mr. Weiss said, his voice raw with emotion.

The words hit her like a blow. “You left her!” she cried, tears streaming down her face.

“You abandoned her—and me! She struggled every day because of you!”

“I know,” he said, his voice barely audible.

“I was a coward. I was afraid of responsibility, afraid of being a father. I’ve regretted it every day. I tried to find her, but she cut all ties. Tell me—where is she now?”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“She’s gone,” Laura spat bitterly.

“She died ten years ago. She got sick, and it’s your fault. She fought so hard to survive, but she was alone because you weren’t there.”

Mr. Weiss crumpled, his body wracked with sobs.

“I never stopped looking. I never stopped loving her. I’m so sorry, Laura. I’m so sorry.”

Laura stared at him, her chest heaving with anger and pain. She shook her head, grabbing her bag.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“I can’t do this,” she said, her voice trembling as she turned and fled the room.

The sound of his sobs followed her as she ran through the grand house and out into the cold night.

Later, Laura sat in the newsroom, her fingers hovering over the keyboard.

The photographs lay beside her, their edges curling slightly under the pressure of her hand.

On her screen, the half-written article glared back at her. This story would blow up—it would ruin Mr. Weiss’s name, tarnish his legacy, and save her job.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

But as she stared at the photos, her chest tightened. Anger and doubt battled in her mind.

Could she really destroy him after everything she had learned? He wasn’t just a stranger anymore. He was her father.

Summoning her courage, Laura stood and walked into Reggie’s office. Her breath felt heavier with each step.

“Reggie, can I come in?”

“Of course,” Reggie said, leaning forward with anticipation. “Please tell me you’ve got something good.”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Laura placed a photograph on his desk. “The article is ready. I can send it over now.”

Reggie’s eyes gleamed as he examined the picture. “This is perfect, Laura! A millionaire’s dirty secrets—this is going to be huge!”

Laura’s hands trembled. Reggie’s words felt like nails on a chalkboard.

“No,” she said suddenly, grabbing the photo back. Without thinking, she ripped it into shreds and tossed them into the air.

“What are you doing?” Reggie roared, his face turning red.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“I won’t ruin his life. If that’s what this job takes, I don’t want it,” Laura said, her voice steady.

“You’re fired!” he shouted.

Laura walked out, her head held high. She had lost her job, but she had found something far more valuable—her integrity.

And for the first time in years, she had a family worth fighting for.

Tell us what you think about this story, and share it with your friends. It might inspire them and brighten their day.

If you enjoyed this story, read this one: “All men are liars.” With these words, Violet ended her radio program. Her life experiences and the countless stories she heard from her listeners had proven it. But, a date with a coworker made her question her belief. After a call from a stranger, she was convinced she had been right all along.

This piece is inspired by stories from the everyday lives of our readers and written by a professional writer. Any resemblance to actual names or locations is purely coincidental. All images are for illustration purposes only. Share your story with us; maybe it will change someone’s life.

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