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.

My Sister Planned a Lie Detector Contest for My Fiancé and Me at My Wedding—the Wedding Was Canceled After Taking It

I always thought my wedding day would be unforgettable for all the right reasons. Instead, it became unforgettable for a reason I could never have imagined. It all began when my sister brought a lie detector test to the wedding.

I’m Harlene, a 28-year-old teacher, and until recently, I thought I had the perfect life. My fiancé, Mark, and I had been together for five wonderful years, planning a future filled with love and laughter. That future vanished the moment my sister, Melissa, turned my wedding into a nightmare.

Let me explain.

A woman standing outdoors | Source: Midjourney

A woman standing outdoors | Source: Midjourney

Mark and I met through a mutual friend five years ago, and from the moment we connected, it felt like we’d known each other forever.

He was very kind and sensitive to everyone’s feelings around him. What I loved the most about him was how he respected everyone equally and never shied away from helping others.

It didn’t take time before we became inseparable. We’d spend weekends exploring new restaurants, binge-watching sitcoms, and dreaming about the future.

“Har,” he’d say with a teasing grin, “if you weren’t such a good cook, I’d probably starve to death.”

A man standing in his house | Source: Midjourney

A man standing in his house | Source: Midjourney

“Good thing I love feeding you,” I’d reply, laughing as he polished off yet another plate of lasagna.

Mark worked as a software developer, a job that sometimes kept him at his desk late into the night. I never minded, though. I understood his dedication and appreciated the effort he put into his career.

As for me, I was living my dream as a teacher. My students were my little rays of sunshine, and I loved every chaotic, beautiful moment of my job.

Children in a classroom | Source: Pexels

Children in a classroom | Source: Pexels

When we decided to get married, we both agreed that our wedding should be a celebration of love and fun. We wanted everyone to feel as happy as we did.

“Let’s make it the kind of wedding people will talk about for years,” Mark said one evening as we brainstormed ideas.

“Definitely,” I replied. “How about games? Fun ones that get everyone involved?”

“Perfect,” he said, his eyes lighting up. “We can have trivia or charades or something. Maybe even a karaoke battle.”

A man talking to a woman | Source: Midjourney

A man talking to a woman | Source: Midjourney

We even looped in my sister, Melissa, for some ideas. At the time, she didn’t seem particularly interested.

“I don’t know,” she said with a shrug. “You guys are the creative ones. Just tell me what to do, and I’ll help.”

With Melissa’s lackluster input, Mark and I continued planning the wedding of our dreams. Every detail mattered to us, from the playlist to the seating chart.

Mark was attentive to everything, from how the napkins matched the centerpieces to ensuring that the cake was perfect.

A wedding planner | Source: Pexels

A wedding planner | Source: Pexels

“This is going to be the best day of our lives,” I told him as we finalized the guest list.

“It will,” he said, squeezing my hand. “I can’t wait to see you walk down the aisle.”

And I believed him. I believed in us. We were the perfect team, and nothing could go wrong.

Little did I know, the wedding we so lovingly planned would turn into a moment I’d wish I could forget.

An upset woman | Source: Pexels

An upset woman | Source: Pexels

The day of the wedding had finally arrived, and I was filled with excitement.

As I stood in front of the mirror, I couldn’t stop smiling. This was it. This was the day I’d dreamed of for so long.

When I walked into the venue, the energy was electric. Everyone seemed to be having a wonderful time, laughing, chatting, and soaking in the atmosphere we’d worked so hard to create.

Mark greeted me at the entrance with a kiss on the cheek.

A woman smiling on her big day | Source: Midjourney

A woman smiling on her big day | Source: Midjourney

“You look stunning, Har,” he said, his voice full of admiration.

“And you look dashing yourself,” I replied with a grin, taking in his crisp suit and the way his eyes sparkled.

Everything felt magical until Melissa grabbed the microphone.

“Alright, everyone!” she called out, her voice cutting through the chatter. “I have a little surprise for the happy couple! I’ve been planning this for weeks, and I promise it’s going to be so much fun!”

I looked at her with wide eyes. I hadn’t heard anything about a surprise game.

A woman at her sister's wedding | Source: Midjourney

A woman at her sister’s wedding | Source: Midjourney

“Melissa, what’s this about?” I asked, walking over to her.

“You’ll see!” she said with a mischievous grin. She waved to a man in the corner, who wheeled in a small machine with wires and sensors.

“What on earth is that?” I asked, my curiosity piqued.

“It’s a lie detector!” Melissa exclaimed, beaming. “I saw this online and thought it would be a hilarious wedding game. You and Mark will answer a few fun questions while hooked up to it. Trust me, everyone’s going to love it.”

A woman talking to her sister | Source: Midjourney

A woman talking to her sister | Source: Midjourney

I glanced at Mark, who gave me a skeptical look but shrugged.

“Why not?” he said. “Let’s give them a show.”

“That’s the spirit!” Melissa exclaimed, clapping her hands. “Come on, let’s get started.”

The technician hooked us up to the machine, and Melissa began with lighthearted questions.

“Mark,” she said with a smirk, “have you ever eaten the last slice of pizza and blamed it on Harlene?”

He laughed. “Yes,” he admitted, to a chorus of laughter from the guests.

A man on his big day | Source: Midjourney

A man on his big day | Source: Midjourney

Next, it was my turn.

“Harlene,” Melissa asked, “have you ever secretly binge-watched a show without Mark?”

“Guilty as charged,” I said, grinning as the detector beeped to confirm I was telling the truth.

The questions continued, each one sillier than the last. Guests took turns coming up with their own, like, “Have you ever lied about liking your partner’s cooking?” or “Did you ever have a crush on a celebrity while dating each other?”

The air was filled with laughter, and I thought this might actually be one of the most memorable moments of the day.

A woman looking straight ahead, smiling | Source: Midjourney

A woman looking straight ahead, smiling | Source: Midjourney

Then Uncle Sam stood up. His usually jovial face was deadly serious as he walked toward the mic.

“Now it’s my turn,” he said, his voice low and deliberate. “Mark, did you ever cheat on my niece?”

Wait, what? I thought. Where did that come from?

I stared at him in silence, while the murmurs filled the air.

Mark chuckled nervously, looking around at the stunned faces.

“That’s a ridiculous question, Uncle Sam. I don’t think I need to dignify it with an answer,” he said, trying to wave it off.

A groom talking to a man | Source: Midjourney

A groom talking to a man | Source: Midjourney

But Uncle Sam wasn’t smiling.

“I think you should, Mark,” he said firmly. “If you’ve got nothing to hide, what’s the harm in answering?”

I felt my heart pounding in my chest.

“Mark,” I said, trying to diffuse the tension, “it’s just a game. Let’s not ruin the mood, okay?”

Mark turned to me, his jaw tight. “Exactly. It’s just a game, and this question is out of line.”

But the look in his eyes gave me pause. There was no humor there, no easy confidence. He looked… defensive.

A groom at his wedding | Source: Midjourney

A groom at his wedding | Source: Midjourney

I tried to reassure myself. This was Mark, my Mark. The man I’d trusted and loved for five years. There was no way he’d cheated on me. Right?

But Uncle Sam wasn’t backing down. “Why not answer, then? If it’s absurd, prove it.”

Mark clenched his fists, his face hardening. “Because it’s insulting, that’s why. I don’t owe anyone an answer to something so ridiculous.”

I glanced around the room, noticing the growing unease among the guests. The whispers, the exchanged glances. My pulse quickened. Why was Mark reacting this way?

A woman at her wedding | Source: Midjourney

A woman at her wedding | Source: Midjourney

“Mark,” I said softly, reaching for his hand. “Answer it so we can move on.”

But he shook his head. “No, Harlene. I won’t dignify this with a response.”

His response told me something wasn’t right.

“Mark,” I said, my voice trembling, “if you don’t answer, I’m not sure I can go through with this wedding. I need to know there’s nothing to hide.”

He looked around and then sighed.

“Fine,” he said, glaring at Uncle Sam. “No, I have not cheated on Harlene.”

A man talking to an older man | Source: Midjourney

A man talking to an older man | Source: Midjourney

Uncle Sam looked at the technician. “He’s lying, isn’t it?”

The technician quickly analyzed the results and nodded. “It looks like a lie.”

The gasp from the crowd was deafening.

“What?” I whispered. How is this possible?”

Uncle Sam smiled.

“Is there anyone in this room with whom you cheated?” he asked.

Mark looked like he’d been cornered. “No,” he said flatly.

“Another lie,” the technician said promptly.

I couldn’t believe it.

“Who, Mark?” I asked. “Who did you cheat on me with?”

A bride talking to the groom | Source: Midjourney

A bride talking to the groom | Source: Midjourney

He didn’t answer.

That’s when I noticed Melissa, my sister, shifting uncomfortably. A horrible thought crept into my mind.

“Was it her?” I asked, pointing at Melissa. “Did you cheat on me with my sister?”

Mark froze. He looked at Melissa before his gaze locked with mine.

“Tell me Mark!” I insisted. “Was it her? Melissa?”

Mark looked at the ground and said what I didn’t want to hear.

“Yes,” he said.

The machine didn’t need to confirm it, but it did. Truth.

A man standing outdoors | Source: Midjourney

A man standing outdoors | Source: Midjourney

The silence in the room was deafening, broken only by my shaky breath. My mind raced as I stared at Mark, then at Melissa, who looked like she wanted to disappear into the floor.

Before I could even form a question, Uncle Sam cleared his throat.

“I wasn’t going to say anything today,” he began, his gaze fixed on Mark. “But I saw you two together a few weeks ago. I was at the mall, grabbing lunch, when I spotted you, Mark, holding Melissa’s hand. I thought maybe I was imagining it until I saw the way you leaned into her. The way you touched her cheek.”

A man and a woman standing in a mall | Source: Midjourney

A man and a woman standing in a mall | Source: Midjourney

He paused, shaking his head in disgust. “It wasn’t how a future brother-in-law behaves with his fiancée’s sister. I hoped I was wrong, but something told me I wasn’t. So, when Melissa showed up today acting nervous and twitchy, I decided it was time to find out the truth.”

His words were like knives, cutting through whatever illusion I’d been clinging to. I looked at Melissa, whose face was streaked with tears. “Why?” I whispered, barely able to speak. “You’re my sister. How could you?”

“Harlene, I…” she started, but her voice cracked, and she couldn’t finish.

A woman talking to her sister | Source: Midjourney

A woman talking to her sister | Source: Midjourney

Then, I turned to Mark. “You didn’t just betray me. You betrayed everything we built together. How could you do this? Why?”

Mark looked away, unable to meet my eyes. “I made a mistake,” he muttered, as if that was supposed to erase the pain he’d caused.

My chest tightened, and my vision blurred with tears. I couldn’t forgive Mark. I knew cheating wasn’t just a mistake. It was a choice, and one I could never accept.

Without another word, I ripped off the wires from the lie detector and walked out, leaving behind the man I thought I knew, the sister I thought I could trust, and the wedding that would never be.

Some betrayals leave scars too deep to heal, and this was one I couldn’t ignore.

A bride running away | Source: Freepik

A bride running away | Source: Freepik

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