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.

Snowstorm Forced Me to Take Shelter in a Stranger’s Home, Only to Discover He Knew My Biggest Secret — Story of the Day

The relentless snowstorm made me seek shelter in a stranger’s home. At first, Justin seemed kind. Too kind. But when I discovered his connection to my biggest secret, everything changed.

That morning, I woke up with a pounding headache. The alarm blared, making the sensation worse. I groaned, fumbling to turn it off, and stared at the ceiling. Something felt off like the day was already conspiring against me.

At work, my boss, Lori, was standing at the head of the table, her sharp eyes scanning the room like a hawk circling prey. Meetings with Lori were less about collaboration and more about survival.

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

“Good morning, team! Before we dive into the numbers,” Lori began, her gaze settling on me, “I have a special assignment.”

My stomach tightened.

“Sophia,” she continued, “you’ll be heading to Montana. There’s a small mountain town where our competitors are testing campaigns. I want you there by tomorrow.”

“Montana?!”

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

“Yes, Montana. You’ll gather intel on their strategies. We need to stay ahead.”

“But it’s Thanksgiving! I had plans.”

Lori cut me off. “Plans can wait. This is business. You’re the best we’ve got for this kind of work.”

I glanced around the room. The silence was deafening.

“I’ll get it done,” I muttered, my hands clenched under the table.

“Excellent! Now, let’s discuss next quarter’s goals.”

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

It felt ridiculous, yet there was no arguing with Lori. She wielded her authority like a weapon, and one wrong move could mean the end of my career.

After the meeting, I opened my laptop. My inbox was already filled with follow-ups from Lori: flight details, a contact list, and a reminder that the trip was “critical” for the company’s success.

I sighed, staring at the cursor blinking in the search bar.

“Montana, here I come,” I muttered, booking the flight.

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

***

I packed my suitcase in record time, and in a few hours, I was seated on the plane, staring out the window at the clouds gathering in the distance.

“Looks like we’re in for some holiday weather,” a voice said beside me.

I turned to see a man settling into the seat next to mine. He had a warm, easy smile and a kind face.

“I’m Justin,” he said, extending a hand.

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

“Sophia,” I replied, shaking it.

The usual polite small talk followed: where we were headed, what we did for a living. Then, after the second glass of sparkling wine, without thinking much, I let it slip.

“Actually, I’m supposed to gather ideas from competitors for my job. I guess you could call it espionage.”

Justin chuckled. “Espionage, huh? Sounds like you’ve got a pretty important job if it’s pulling you away from Thanksgiving.”

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

“Well, somebody has to do it,” I said lightly, though the bitterness crept into my voice.

The flight passed fast thanks to Justin’s friendly conversation. But the moment we landed, the storm was full-blown chaos. Snow piled up against the terminal windows.

“All flights are canceled until further notice,” the intercom blared.

I sighed, pulling my coat tighter around me. The thought of spending the night in the freezing terminal made my headache return.

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

“Rough day?” Justin appeared again, dragging his suitcase.

“You could say that.” I showed him the fully booked hotel listings on my phone.

“Well. I live nearby. It’s not fancy, but you’re welcome to stay.”

I blinked at him. “Are you sure?”

“It’s better than freezing here. Come on.”

Grateful and too tired to argue, I followed him out into the snowy night.

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

***

When we arrived at Justin’s house, the snow was falling in thick, quiet flakes. The world outside was still, as though the storm had tucked everything in for the night.

“Everyone’s asleep,” Justin said, taking off his boots by the door. “I’ll show you to the guest room.”

I followed him up a narrow staircase. The house had a lived-in charm — family photos lined the walls, and the faint scent of pine lingered in the air. Justin opened a door and flicked on the light.

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

“Here you go,” he said. “Make yourself comfortable. There are extra blankets in the closet if you need them. I’ll leave some tea and dinner for you downstairs.”

“Thanks.”

As he left, I glanced around the room. Suddenly, I noticed a photo on the wall. It was Justin, smiling broadly, with a group of employees in front of a sign. The logo on the sign was unmistakable. My stomach dropped.

Justin is the competitor!

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

Before I could process the shock, my phone started buzzing on the nightstand. I groaned, knowing exactly who it was. Sure enough, Lori’s name flashed across the screen. Reluctantly, I answered.

“Well, well,” Lori’s voice crackled through the line, filled with satisfaction. “Looks like you’re exactly where you need to be.”

“Lori,” I began, keeping my voice low, “this isn’t…”

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

“Listen, Sophia,” she cut me off. “I don’t care about your excuses. You’re there to get the job done. Dig through his files, find out what projects they’re working on, and send me everything. Don’t forget, I can make it look like this was all your idea. Clients won’t trust someone who spies on their own. Understood?”

Her words were ice in my veins. I hesitated, torn between guilt and the crushing pressure of her threats.

“Fine,” I muttered finally.

The call ended, leaving me feeling like I’d just made a deal with the devil.

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

***

Hours later, when Justin’s house had gone completely quiet, I crept downstairs. His office door was slightly ajar, the glow of his laptop casting faint shadows.

My hands shook as I searched through his files, stopping when I spotted a flash drive inserted into the laptop.

That’s it! All in there!

Just as I reached for it, I heard a small voice.

“Hi,” a little girl said, rubbing her eyes. “I’m Liv.”

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

“Hi, Liv,” I whispered, glancing nervously toward the hallway. “Shouldn’t you be in bed?”

“Are you playing hide-and-seek?”

Before I could respond, Justin’s voice called softly, “Liv? What are you doing up?”

I panicked, ducking under the desk and motioning for Liv to keep quiet. She gave a tiny nod.

Justin appeared in the doorway, scooping her into his arms. “Come on, sweetheart. Let’s get you back to bed.”

As they left, I grabbed the flash drive, tucked it into my pocket, and slipped back to my room.

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

***

The following morning, I intended to leave quietly, avoiding an awkward goodbye, but Justin and Liv were already at the kitchen table.

“Morning,” Justin greeted, his warm smile lighting up the room. “You must be starving after all that travel. Come on in.”

I stepped hesitantly into the cozy kitchen, the scent of fresh coffee and pancakes drawing me in. Liv was drawing at the table.

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

“Hi! I am Liv,” she said brightly.

Then, to my surprise, she raised a finger to her lips and whispered, “Shh,” mimicking the gesture I’d made to her the night before.

My cheeks flushed. “Hi, Liv! I am Sophia. Could I see your masterpiece?”

Did she remember everything?

“Yup!” She giggled, giving me her picture. “Daddy says we’re making pancakes for you. I helped with the batter.”

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

“She’s the head chef this morning,” Justin chimed in, flipping a pancake on the stove.

“Thanks for letting me stay last night. It was kind of you.”

“Not a problem. Storm like that? You’d have frozen at the airport.”

Liv hopped down from her chair and skipped over to the counter. She picked up a plate piled high with golden pancakes and walked it over to me, balancing it carefully with both hands.

“Daddy, can we have whipped cream on them?” Liv asked, tugging at Justin’s sleeve.

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

“You have to ask our guest first. Does Sophia like whipped cream?”

Liv turned to me. “Do you?”

“Of course,” I said, laughing. “Who doesn’t?”

Liv clapped her hands. As she sprayed a generous swirl onto her pancake, she glanced at me again, her finger returning to her lips in a playful “shh.”

My heart sank slightly.

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

She did remember!

Justin slid into the seat across from me. As we ate, he shared his story.

“After Liv’s mom passed away during childbirth,” he began, “it was just the two of us. Balancing parenthood and running the company hasn’t been easy, but Liv’s my reason for everything.”

Liv looked up from her pancakes, her face glowing with pride. “Daddy works hard, but he always has time for me.”

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

This man isn’t just kind. He is incredible! And I betrayed his trust the night before.

Justin leaned back, his gaze thoughtful. “What about you, Sophia? What drives you?”

What can I say? That my job feels like a race I could never win? That I don’t even know what I am chasing anymore?

“I guess I’ve been so focused on my career that I haven’t stopped to think about it,” I admitted, pushing my fork into the last bite of pancake. “Maybe it’s time I do.”

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

The warmth of the moment was shattered when my phone buzzed loudly on the table. Lori’s name flashed across the screen. I excused myself and stepped outside. The cold air bit at my cheeks as I read her latest message:

“Where is the file, Sophia? If you don’t send it now, you’re done. Fired. And don’t think you’ll find work elsewhere. I’ll make sure no one hires you again.”

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

I stared at the phone. My career, my reputation… It was all on the line. But then I thought about Justin’s story and Liv’s trust in her Dad.

Can I really betray that?

I turned back toward the house, walked over, and held out the flash drive to Justin.

“Here. I can’t do this. I’m sorry.”

He looked at me, then nodded. I grabbed my coat and bag, said a quick goodbye to Liv, and walked out the door, fighting back tears.

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

At the airport, I waited for my flight, staring at my phone as Lori’s messages piled up.

“You’re done. You’ll regret this. You’re fired!”

My future felt uncertain, and fear clawed at me. But before I could spiral further, I heard a familiar voice.

“Sophia.”

I turned to see Justin standing there, holding Liv’s hand. My heart almost stopped.

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

“I knew everything from the start,” he said calmly. “Liv told me about ‘hide-and-seek,’ and I recognized your company’s name on your documents on the plane. Lori and I have crossed paths before.”

“Why didn’t you say anything?”

“I invited you because I liked you. Even after everything, I could see you weren’t the kind of person to go through with something like this. I wanted to see what you’d choose. And you made the right choice.”

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

“Daddy says you can stay for Thanksgiving. Will you?”

Justin smiled softly. “The offer still stands.”

I didn’t have to think long. “I’d like that.”

That Thanksgiving, as snow blanketed the world outside, I felt a warmth of home. Perhaps that was the start of a life filled with meaning, love, and the promise of a future with Justin and Liv.

For illustration purposes only | Source: Midjourney

For illustration purposes only | Source: Midjourney

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