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.

Daughter Discovers Sealed Letter in Attic, But Her Mom’s Reaction Left Her Speechless

Chloe visited her sick mother, Helen, every week. One day, while at her mom’s house, she decided to clean the attic. It seemed like no one had been up there for years. While cleaning, she found a box of old letters that could hold the answer to her biggest question—why her father left. But one letter stood out. It was sealed and had never been opened.

Source: Midjourney

Chloe, now 34, had been coming to visit her mother more often recently. Helen’s health had gotten worse, and she was now bedridden and weak.

Chloe couldn’t shake the fear that any visit could be the last. This feeling hung over her heart constantly.

Every week, Chloe would come by with groceries. She cooked meals for her mother and handled the tasks that Helen could no longer do.

Source: Midjourney

It was hard for Chloe to watch her once-strong mother, Helen, grow so weak. But Chloe knew it was important to be there, no matter how difficult it felt.

One chilly afternoon, Chloe stood in the kitchen, stirring a pot of soup. The smell of chicken and herbs filled the room, and the bubbling of the broth was the only sound.

But then Helen’s sharp voice broke the silence from the living room.

“You know, at your age, I already had you,” Helen called, sounding irritated. “When are you going to have children?”

Chloe tensed, gripping the spoon tighter. Her mother had made this comment before, but it always hurt.

Source: Midjourney

Helen had grown more critical with age. She often commented on Chloe’s lack of children, her career, or her relationship. Chloe tried not to let it get to her, but it was tiring.

“Maybe one day, Mom,” Chloe replied softly, not wanting to argue since Helen wasn’t well enough for it.

Source: Midjourney

After feeding Helen and making sure she was comfortable, Chloe tidied up the kitchen. The house was a mess since her mother’s illness had worsened, and there was always so much to do.

Source: Midjourney

When Helen finally fell asleep, Chloe decided to tackle a bigger job—the attic. No one had been up there for years, and it was time to clean it out.

Source: Midjourney

The attic was dimly lit, with thick layers of dust covering everything. Cobwebs hung in the corners, and the air smelled musty.

As Chloe sorted through old belongings, something caught her eye—a small box in the corner. She pulled it out and saw it was locked. After finding a hammer, she gently tapped the rusty lock until it broke.

Source: Midjourney

Inside were dozens of old letters, yellowed with age. Chloe’s breath caught as she realized they were love letters from her father—the man she had never known.

Source: Midjourney

Each letter was filled with love and promises to return soon. Her father had been an actor, traveling with a theater troupe. In his letters, he sent money and wrote about missing Helen. Chloe was completely absorbed, learning about a love story she had never heard.

Source: Midjourney

At the bottom of the box, Chloe found one final letter. It was still sealed, as if waiting all these years. Her heart raced—why hadn’t her mother opened it? What secrets did it hold?

Source: Midjourney

Chloe knew she couldn’t open it without asking her mother first, no matter how badly she wanted to know the truth.

She went to her mother’s room, where Helen was awake. Chloe hesitated, knowing this would upset her.

“Mom, I found a box of letters in the attic. They’re from Dad,” Chloe said carefully.

Source: Midjourney

Helen’s face hardened, and she snapped, “What were you doing going through my things?”

“I was just cleaning,” Chloe answered quickly. “But there’s one letter you never opened. Why?”

Helen’s face flushed with anger. “Burn them! I never opened that letter for a reason. You will never read it! Swear it!”

Chloe was shocked. “But Mom, don’t I have a right to know? He’s my father, and I know nothing about him.”

Helen sighed deeply, too exhausted to argue anymore. Chloe, feeling defeated, left the room, still holding the unopened letter.

Chloe sat in the living room, staring at the sealed envelope. This letter might finally reveal why her father had left, but part of her didn’t want to open it. What if the truth was worse than the mystery?

After a long pause, Chloe took a deep breath and opened the letter. Her heart sank as she saw it was charred, but the message was clear: her father loved Helen and their unborn child. He had promised to come back.

Behind it was another letter, from her father’s best friend, explaining that her father had died a hero, saving people from a fire during one of his performances.

Chloe rushed back to her mother’s room, demanding, “Why didn’t you tell me? Dad loved us!”

Helen’s voice trembled as she explained, “He loved us, but he loved his work more. He stayed behind to help people in a fire and died.”

Chloe was stunned. “He died… a hero?”

Helen nodded. “I couldn’t read that letter. I wanted to forget.”

Chloe sat down beside her mother. “Do you want me to read it to you?”

Helen hesitated but smiled through her tears. “I’d love that.”

With a deep breath, Chloe began to read her father’s final words aloud, letting the love he left behind fill the room.

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