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.

Little Girl Stopped Me on the Street and Said, ‘Your Picture Is in My Mom’s Wallet!’ – When I Saw Her Mom, I Was Speechless

While jogging through a quaint seaside town, I was stopped by an insistent little girl who claimed, “Your picture is in my mom’s wallet!” Curious and uneasy, I followed her to a charming house. When her mother appeared, I was shocked speechless!

The ocean breeze hit differently here, away from the urgency I was used to back in Silicon Valley.

A man staring out at the ocean | Source: Midjourney

A man staring out at the ocean | Source: Midjourney

I’d forgotten what it felt like to breathe without checking my phone every few seconds. My sister had practically pushed me onto the plane, insisting I needed this break from running my tech empire.

She’d insisted the beautiful beaches, great surfing, and lack of crowds made it the perfect place to relax. Looking back now, I wonder if she knew what she was setting in motion.

I’d been in this small coastal town for three days, and while its charm was undeniable — all weathered boardwalks and salt-sprayed storefronts — I felt like a fish out of water.

A man walking down the street in a coastal town | Source: Midjourney

A man walking down the street in a coastal town | Source: Midjourney

The locals moved at their peaceful rhythm, while I still vibrated with the energy of quarterly reports and board meetings. Even my temporary rental cottage, with its shabby-chic furniture and views of the sunset, felt like someone else’s life I was trying on for size.

That morning, I decided to burn off some of this restless energy with a run through the quiet streets.

The fog was just lifting, and the early sun painted everything in soft gold. My expensive running shoes felt out of place on these worn sidewalks, just like I did.

A man jogging down a street | Source: Midjourney

A man jogging down a street | Source: Midjourney

A few early risers nodded hello as they walked their dogs or opened their shops. Their easy smiles made me realize how long it had been since I’d exchanged simple pleasantries with strangers.

“Mister, wait! Mister! I know you!”

I froze mid-stride, my heart suddenly racing faster than my run had caused. A little girl, maybe eight years old, was running toward me, her wild curls bouncing with each step.

An excited girl running down a misty street | Source: Midjourney

An excited girl running down a misty street | Source: Midjourney

Before I could process what was happening, her small hand grabbed mine.

“Mister, come with me! To my mom! Come on!”

I gently but firmly pulled my hand away, alarm bells ringing in my head. “Wait, little one. What’s your name? And how do you know me?”

She looked up at me with eyes so earnest it almost hurt. “My name’s Miranda! Your picture is in my mom’s wallet! I see it all the time!”

A girl smiling up at someone | Source: Midjourney

A girl smiling up at someone | Source: Midjourney

Her words hit me like a physical blow. My picture? In her mom’s wallet? I took a step back, my mind racing through possibilities.

“Miranda, that’s… that’s impossible. I don’t know anyone here.”

“Yes, you do! You know my mom!”

She reached for my hand again, but I kept it safely at my side. The morning sun caught her features just right, and something about her profile tugged at my memory, but I couldn’t place it.

A man on a misty street | Source: Midjourney

A man on a misty street | Source: Midjourney

“Listen, I can’t just follow a child I don’t know. Who’s your mom? And why would she have my picture?”

“Julia! My mom’s name is Julia!” She bounced on her toes, practically vibrating with excitement. “She looks at your picture sometimes when she thinks I’m not watching. She gets all quiet after.”

Julia? I searched my memory, but the name only brought up vague recollections of business meetings and casual introductions. Nothing significant enough to warrant having my photo in anyone’s wallet.

Yet something about this child’s certainty made me hesitate to just walk away.

An insistent young girl speaking to someone | Source: Midjourney

An insistent young girl speaking to someone | Source: Midjourney

“Come on, come on!” Miranda tried to grab my hand again, but I shook my head.

“I’ll walk with you, but no hand-holding, okay? I don’t want anyone thinking I’m up to no good.”

She nodded, accepting this compromise, and skipped ahead of me, looking back every few steps to ensure I was following.

We walked down a street lined with mature oak trees, their branches creating dappled shadows on the sidewalk. Finally, we reached a modest house with white shutters and a garden full of bright flowers.

A modest house surrounded by a garden filled with flowers | Source: Midjourney

A modest house surrounded by a garden filled with flowers | Source: Midjourney

Miranda bounded up the steps and threw open the door, disappearing inside.

“Mom! Mom! He’s here! He’s here! The man from your wallet! He’s here!”

I stood awkwardly in the hallway, wondering if I should leave before this got even more bizarre. But then Miranda reappeared, practically dragging a woman behind her.

The woman froze when she saw me. Her hand flew to her mouth, and tears immediately welled in her eyes.

A woman standing in a hallway with one hand over her mouth | Source: Midjourney

A woman standing in a hallway with one hand over her mouth | Source: Midjourney

I didn’t recognize her at first, not until she lowered her hand, and eight years of buried memories came crashing back.

“What? How is this possible?” I whispered. “Meredith? Is that you?”

“Nobody’s called me that in years,” she said, her voice thick with emotion.

The world tilted on its axis as I looked between her and Miranda.

A woman with a shocked expression standing in an entrance hallway | Source: Midjourney

A woman with a shocked expression standing in an entrance hallway | Source: Midjourney

The same wild curls, the same determined set to their jaws. My throat went dry as understanding began to dawn.

“You left, remember?” Julia’s words came out sharp and bitter. “That day at the café. You told me you didn’t want to be with someone who only cared about your money.”

The memory hit me like a punch to the gut. My sister had shown me documents — fabricated documents, I now realized — claiming Julia had a history of pursuing wealthy men, and that she had debts she was trying to pay off.

An astonished man standing in an entrance hallway | Source: Midjourney

An astonished man standing in an entrance hallway | Source: Midjourney

I had believed it all without question, too caught up in my fears of being used to see what was right in front of me.

“You never even let me speak,” Julia continued, tears streaming down her face. “You accused me of chasing after rich men and told me your sister showed you documents detailing my debts. I never had any debts.”

She paused then and looked down at Miranda, her voice softening. “I knew that if I told you about the baby, it would only confirm your sister’s lies about me. And I couldn’t do that because I truly loved you. And… I have my pride.”

A woman leaning against a wall while her daughter stands on something behind her | Source: Midjourney

A woman leaning against a wall while her daughter stands on something behind her | Source: Midjourney

Miranda stood between us, her small hand clutching her mother’s, looking confused by the tension she’d created. My daughter!

The thought hit me with such force that I had to lean against the wall for support. All these years of building my company, of chasing success, and I’d had a child I didn’t even know about.

“Why ‘Julia’?” I managed to ask, trying to make sense of anything in this moment. “Why did you go by Meredith back then?”

A man leaning forward slightly while speaking to someone | Source: Midjourney

A man leaning forward slightly while speaking to someone | Source: Midjourney

“Meredith was my middle name. I used it that year because I’d just lost my grandmother. She was also called Meredith. I thought you knew that. But I guess there were a lot of things you didn’t know about me. You were always so busy…”

Everything clicked into place with devastating clarity. My sister’s manipulation, her pushing me to date her best friend after Meredith and I broke up, the convenient “evidence” of Julia’s gold-digging ways.

I’d been such a fool, so wrapped up in my ambitions and fears that I’d missed what really mattered.

A man astounded by a realization | Source: Midjourney

A man astounded by a realization | Source: Midjourney

“I was wrong,” I said, my voice cracking. “About everything. I believed lies, and I let them ruin us. But now… now I want to make it right.”

Julia’s laugh was hollow. “How do you make up for eight years? For a child growing up without a father? For all the school plays and violin recitals and birthday parties you missed?”

“I can’t,” I admitted, feeling the weight of every missed moment. “But I can be here from this moment forward, if you’ll let me. For Miranda. For both of you.”

A man speaking earnestly to a woman | Source: Midjourney

A man speaking earnestly to a woman | Source: Midjourney

Miranda’s eyes lit up at this, but Julia’s expression remained guarded.

“Words are easy,” she said. “Especially for a man who makes his living selling dreams to investors.”

“Then let me prove it with actions,” I insisted. “I’ll move here. Take a step back from the company. Whatever it takes. I’ve spent so long building something I thought was important, but standing here now, I realize I was building the wrong thing all along.”

A man looking stricken | Source: Midjourney

A man looking stricken | Source: Midjourney

“Daddy?” Miranda’s voice was small but hopeful, and it shattered what was left of my heart. That one word held so much: all the years I’d missed, all the possibilities ahead.

Julia’s shoulders slumped slightly. “We can try,” she said finally. “But slowly. And at the first sign that you’re going to disappear again…”

“I won’t,” I promised. “I’ve spent eight years chasing success, thinking it would fill this empty space inside me. But standing here, looking at both of you… I finally understand what matters.”

A man appealing to someone | Source: Midjourney

A man appealing to someone | Source: Midjourney

Miranda launched herself at me, wrapping her arms around my waist. After a moment’s hesitation, I hugged her back.

Julia’s expression was still cautious, but there was something else there too — a tiny spark of hope that matched the one growing in my own heart.

The morning sun had burned away the last of the fog, and the sea breeze carried the sound of distant waves and seabirds. Through the open door, I could hear wind chimes singing their gentle song.

Wind chimes hanging on a porch | Source: Midjourney

Wind chimes hanging on a porch | Source: Midjourney

My sister had been right about one thing — I had needed this break from my normal life. But instead of just finding rest, I’d found something I hadn’t even known I was missing: a chance to reclaim the family I’d almost lost forever.

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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