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.

Working as a Waitress at a Wedding, I Froze When I Saw My Own Husband Dressed as the Groom — Story of the Day

While serving at a wedding, I suddenly spotted the groom—it was my husband, David. Seeing him with another woman, pretending to be someone else, sent my world crashing down. In that moment, everything I thought I knew about my life was turned upside down.

Oh, weddings… They always had a way of stirring up old memories, bringing me back to that day when David and I said our vows. Our wedding wasn’t anything grand or over the top—far from it, actually.

For illustration purposes only. | Source: Pexels

For illustration purposes only. | Source: Pexels

We were just two young people in love, not concerned about fancy decorations or a big reception. Even now, after seven years of marriage, those memories still brought a smile to my face.

Working as a waitress for a catering company meant that I was always around weddings. Every time I walked into a beautifully decorated hall, the smell of fresh flowers in the air, I couldn’t help but think back to our simple ceremony. If only I had known how fragile things could be…

That day, just like any other, we arrived early to set everything up before the guests and the newlyweds showed up.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

About an hour later, the guests started arriving, their excited chatter filling the hall as they waited for the bride and groom to return from their photo session. I was in the restroom when Stacy, my colleague, burst in, her face pale with worry.

“Lori, listen,” Stacy said, her voice shaky, “I think you should go home.”

“Go home? Why would I do that?” I asked. “Are you trying to get more shifts for yourself? Sorry, but I need the money just as much as you do.”

Stacy shook her head, looking more nervous than I’d ever seen her. “No, Lori, you don’t understand. I really think you shouldn’t be here.”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“What are you talking about? Why are you acting so weird?” I said. “Stacy, seriously, what’s going on?”

She bit her lip, glancing toward the hall. “You’re not going to like what you see.”

I headed back to the hall, my mind racing with thoughts of what Stacy had said. My heart nearly stopped when I saw the bride and groom. Stacy was right—I shouldn’t have come.

There, standing in front of all the guests, was David… my David. The man I had shared my life with for seven years, now standing with another woman.

For illustration purposes only. | Source: Pexels

For illustration purposes only. | Source: Pexels

My breath caught in my throat. I felt like the ground had been ripped out from under me. I couldn’t make sense of what I was seeing. I turned and ran outside, tears streaming down my face. It was like a nightmare, one I couldn’t wake up from.

Outside, I collapsed against the wall, gasping for air. My vision blurred with tears, but I forced myself to look at the sign with the bride and groom’s names: “Welcome to the wedding of Kira and Richard.” Richard? What a liar!

Stacy rushed outside. She tried to speak, to comfort me, but I couldn’t hear her. All I could think about was how he had betrayed me. I wiped my tears away, anger building inside me. I wasn’t going to let him get away with this. No way. I was going to ruin this wedding and expose him for the fraud he was.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

I returned to the hall just as the bride and groom were giving their first toast. My heart pounded in my chest, but I knew I had to do this.

I marched straight up to David and snatched the microphone right out of his hand. He looked at me, his face full of shock and anger, but I didn’t care. He deserved every bit of what was coming.

“I have an announcement!” I shouted into the microphone, my voice echoing through the hall. Every head turned toward me, the room falling into a stunned silence.

The bride, this poor woman, clung to David like he was her lifeline. She looked at me with wide, fearful eyes, clearly not understanding what was happening.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“David, or as you all know him, Richard, has deceived you all!” I began, my voice trembling with rage. “He’s already married! To me!” The words hung in the air like a bomb that had just gone off. Gasps rippled through the crowd, and I could see the confusion and disbelief on their faces.

“What?” the bride stammered, her voice barely above a whisper. She turned to David, her eyes filling with tears. “Richard, what’s going on? Who is this woman?”

David shook his head, his face a mask of feigned confusion. “I… I don’t know,” he stammered. “I’ve never seen this woman in my life.”

“Seven years of marriage, and you were blind?!” I shouted, feeling my anger boil over.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“What? What seven years of marriage?” he asked, still trying to play dumb.

“Stop pretending you don’t know me,” I said. “You’re only making it worse, David.”

“My name is Richard!” he shouted back, his voice desperate. “I have no idea who your David is. You’re crazy!”

“Oh, really?” I said, narrowing my eyes. “Then what’s this?” I pulled out my phone, the screen lit up with a picture of our wedding day. I held it up for everyone to see. The room fell into a deeper silence as people strained to get a look.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

The bride, Kira, stepped closer, her eyes locking onto the image. “Richard…?” she asked, her voice trembling. “How could you do this to me? How could you lie to me like this? And to her?” She pointed at me, her hand shaking as tears spilled down her cheeks.

“Kira,” Richard said, his voice softening as he reached for her. “I swear, I don’t know who this woman is or why she has a photo with me. I would never hurt you.”

But the bride shook her head, backing away from him. “I loved you, Richard… or David, or whoever you really are,” she said, her voice breaking. “How could you betray me like this? I don’t even know who you are anymore.”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“I’m Richard,” he insisted, desperation creeping into his voice. “And I love you, Kira. I’m telling the truth!”

I couldn’t hold back a bitter laugh. “He’s probably only with you for your money,” I said, the words dripping with contempt.

“Shut up!” David yelled, his voice raw with anger and fear.

The bride shook her head, tears streaming down her face. “No, Richard, I can’t do this. I can’t be with someone who could lie like this, who could do something so awful.”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

She turned to me. “I’m sorry,” she whispered. “I really didn’t know.”

“It’s not your fault,” I replied, my voice softening. “He deceived us both.”

“Kira, please,” David begged, but it was too late. She was already turning, running toward the door, her wedding dress trailing behind her like a broken dream.

Without a second thought, David bolted after her. “Kira! Wait!” he shouted as he disappeared through the doors after her, leaving the stunned guests and me standing there in silence.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

I stormed outside, ready to tell David I was done and filing for divorce. But when I found him, he was sitting on the curb, tears streaming down his face.

“Of course, play the drama,” I said, crossing my arms.

He looked up, his face twisted with anger. “You! This is all your fault!” he shouted. “My wife ran away from me, and it’s because of you! Some crazy waitress!”

“I’m the crazy one?!” I yelled back. “You’re the one who married another woman while still being married to me!”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“I’m not your husband! I’ve never seen you before in my life!”

“Oh, really?” I challenged, pulling out my phone. “Then let’s call David, who you claim you’re not, and see what happens.”

“Go ahead, call him!” he snapped.

I dialed David’s number, putting it on speaker, but the phone just kept ringing. “How strange that you’re not picking up,” I said, my voice dripping with sarcasm.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Then, suddenly, the ringing stopped, and I heard his voice. “Yes, dear. Is everything okay?”

“What the…?” I stammered, staring at the man in front of me.

“I told you I’m not your husband!” he said, his voice calmer now, but still tense.

“Honey,” I said into the phone, trying to keep my voice steady, “I think you should come here; something strange is going on.”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

David arrived about half an hour later. For what felt like forever, he and Richard just stood there, staring at each other in complete silence. It was like looking into a mirror—they were identical in every way.

Finally, Richard broke the silence, turning to me with a wry smile. “Well, if I were in your shoes, I would’ve done the same,” he said.

David’s eyes shifted to me, filled with hurt and confusion. “How could you think I would do something like this to you?” he asked quietly.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“He’s your exact double,” I blurted out, desperate to make him understand.

“Yes,” David replied, his voice soft. “But it still hurts that you thought that.”

“I’m sorry, honey. I was just so angry and hurt,” I said, reaching for his hand.

As it turned out, Richard and David were both adopted from the same orphanage when they were just babies. But they were taken in by different families. They had no idea the other existed. I couldn’t believe what I was hearing. My husband had a twin brother he never knew about.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“But that doesn’t change the fact that my wife hates me,” Richard said, his voice filled with despair.

“We’ll fix that,” I replied.

“Yes, get in my car, and let’s go,” David added, already moving toward the car.

“She’ll never forgive me,” Richard muttered.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“She will when she sees David,” I assured him.

We drove in silence to the hotel where Kira was likely staying. We went to her room, but she wouldn’t let us in. I could hear her crying through the door, and it broke my heart.

We didn’t give up. We stood outside under her window, shouting up at her, trying to get her attention. Finally, she looked out the window, her eyes red from crying.

“Kira!” I shouted, waving my arms to get her attention. “Your fiancé didn’t lie to you! And my husband didn’t cheat on me! Look!” I pointed to Richard and David, who stood side by side, identical in every way.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Kira’s eyes widened in shock. “How is this possible?!” she shouted down at us.

“We were separated in the orphanage!” Richard shouted back.

For a moment, she just stared at us, then she closed the window, and our hearts sank.

“See? I told you she wouldn’t forgive me,” Richard said, his voice heavy with defeat. But just as the words left his mouth, the door burst open, and Kira ran out, tears streaming down her face. She threw her arms around Richard and kissed him, holding him tight.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

David pulled me into a hug. “I’m sorry I doubted you,” I said softly, looking up at him.

David smiled, brushing a strand of hair from my face. “Oh, I think I would’ve done the same. Honestly, I’m flattered that after seven years of marriage, you’re still willing to fight for me.”

I laughed, nudging him playfully before leaning in to kiss him. So, my husband gained a brother, and I gained a friend I can’t imagine my life without.

For illustration purposes only. | Source: Pexels

For illustration purposes only. | Source: Pexels

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: My son Scott, who had never dated anyone, suddenly showed up with a sweet girl and announced they were getting married next week. I was shocked, thrilled, and confused all at once. But as the truth unraveled, I realized our family was about to face a challenge I never saw coming.

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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