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.

This $30 Cake Destroyed My Marriage – My Husband Broke Down in the Middle of His Birthday Party

At Tom’s lively birthday celebration, a seemingly innocent cake delivery unexpectedly turned the atmosphere from festive to frosty. When the cake was unveiled, revealing a shocking secret, the room fell into stunned silence as Tom’s betrayal was laid bare for friends and family to see.

I was rushing around the house, making sure everything looked perfect for Tom’s birthday party. Balloons floated in corners, and streamers hung from the ceiling, adding pops of color everywhere.

The living room buzzed with laughter and chatter as early guests started to arrive, bringing with them the warm, comforting smell of home-cooked dishes and the sound of cheerful greetings.

In the midst of setting up the snack table, the doorbell rang. I wiped my hands on my apron and hurried to answer it. A delivery man stood there, holding a large box with a cheerful “Happy Birthday!” sticker plastered on the side.

“For you,” he said, handing me the box that was surprisingly heavy.

“Oh, I didn’t order this,” I murmured, more to myself than to him, as I signed for the package. I assumed it was a surprise from one of Tom’s friends or his family. Busy as I was, I thanked him quickly and placed the cake box on the kitchen counter to deal with later.

As the party filled up, Tom was the center of attention, laughing and clapping his friends on the back. He always had this easy charm that made everyone feel welcome. His parents, Jane and Michael, brought in a homemade pie, smiling broadly.

They hugged me, praising the decorations and the cozy atmosphere. My best friend Lisa was right behind them, her arms laden with gifts and her kids in tow, adding to the joyful chaos.

In the kitchen, I finally had a moment to slide the mysterious cake into the fridge. Curiosity got the better of me, and I lifted the lid just enough to sneak a peek. There was a picture on the cake, but it wasn’t the happy birthday message I expected. It looked like a screenshot of a text conversation, but I couldn’t make out the details.

“Need any help in here?” Lisa’s voice snapped me back to reality.

I quickly closed the cake box, plastering a smile on my face. “Just trying to make room for everything,” I replied, pushing the box into the fridge.

As we walked back to the living room, I shook off the uneasy feeling. It was probably just a quirky joke from Tom’s work friends, I thought. They always tried to outdo each other with humorous gifts.

The party buzzed with energy, everyone enjoying the food and music. Tom’s laughter mingled with the happy chatter of our friends and family. I moved through the crowd, refilling drinks and sharing laughs, my mind occasionally drifting back to the odd cake in the fridge.

I decided to wait until we were ready to cut it. After all, it was just a cake, and it wouldn’t spoil the night I had spent weeks planning. But deep down, I couldn’t shake the nagging thought that something was off.

The room was lively, filled with the warmth of close friends and family, all gathered to celebrate Tom’s birthday. As the clock ticked closer to cake time, I felt a surge of energy.

I excused myself, heading back to the kitchen to retrieve the cake. My hands were steady but my heart wasn’t. The earlier unease had settled in my stomach, a constant reminder that something might be amiss.

As I rolled the cake out on the cart, the guests gathered around, their voices rising in a chorus of “Happy Birthday.” Tom’s face lit up with a broad smile, his eyes twinkling in the glow of the candles. Everyone cheered, clapping him on the back, waiting for the grand reveal of the cake.

I took a deep breath and lifted the lid off the cake box. The room fell silent in an instant. All eyes were glued to the cake, not because of its design or size, but because of the image plastered across it—a screenshot of a text conversation between Tom and someone named Jenna. The messages were clear, unmistakably intimate, words no wife should ever have to read about her husband.

Whispers cut through the silence. “What is that?” “Is this some kind of joke?”

Tom’s face drained of color. He looked from the cake to me, his mouth opening but no words coming out.

I found my voice, though it trembled. “Tom, what is this?” I asked loudly, the room echoing my question in their hushed murmurs.

“It’s not what it looks like, Ella,” Tom stammered, his eyes darting around the room as if looking for an escape.

“Not what it looks like?” I repeated, my voice rising. “It looks like you’ve been cheating on me, Tom. With Jenna? Who is Jenna?”

The room was heavy with shock, Tom’s friends and family looking from him to me, unsure of where to stand or what to say. His mother covered her mouth with her hand, tears in her eyes.

“Ella, I can explain,” Tom said, reaching out to me. I stepped back, refusing his touch.

“Explain? In front of everyone? You owe me that much, don’t you?” I demanded, my hands shaking but my voice firm. The cake, once a symbol of celebration, now sat between us—a stark, sweet betrayal.

Tom looked around, the weight of the eyes on him too much to bear. “I’m sorry,” he whispered, but the words were hollow, lost in the larger echo of his deceit.

The party was over. The silence said it all. No more laughter, no more chatter. Just a room full of people stunned by the truth laid bare on a $30 cake.

Tom attempted to speak, to salvage some shred of dignity, but his explanations faltered against the undeniable truth displayed for all to see. “It was a mistake,” he kept saying, but the words sounded empty, meaningless.

One by one, the guests made their excuses and left, leaving behind a wake of cold, uneaten cake and broken promises. Finally, Tom was left alone in the center of the chaos he had caused, isolated even in his attempts to explain.

With the last guest gone, the silence of the house was deafening. I sat in the quiet, the remnants of the party around me, and thought about everything Tom and I had built together. Love, trust, years of memories—all tainted now. The pain of the betrayal was sharp and deep, but even in the midst of it, a resolve was forming within me.

I knew what I needed to do. Respect and trust were the foundations of any marriage, and once they were gone, what was left to build on? I couldn’t live in the shadow of Tom’s choices. It was not just about what I had learned today; it was about self-respect, about not settling for someone who could so easily deceive me.

I decided to end our marriage. It was not a decision made out of anger, but out of a profound need to reclaim my life and my self-worth. As I stood up, the empty house seemed to echo back my resolve, its emptiness a mirror of what remained of our relationship.

Stepping outside, I looked back at the home that had harbored so many dreams and secrets. Tomorrow, I would start anew, building a life marked not by what I had lost, but by what I had chosen to gain: my freedom and dignity. The night was quiet, and in its silence, I found my first moment of peace.

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