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.

Our Stepdad Gifted My Mom a Pack of Toilet Paper for Her Birthday — Our Revenge on Him Was Harsh

My stepdad always made a big deal about being the “man of the house,” but when his “special gift” for my mom’s birthday turned out to be a pack of toilet paper, I decided it was time for payback. And let’s just say someone else ended up desperately needing that present.

My stepfather, Jeff, loved reminding us he was the breadwinner of the house throughout our entire childhood. Anytime we sat down to dinner, he’d start with his usual spiel.

A man lauhing at a dinning table | Source: Midjourney

A man lauhing at a dinning table | Source: Midjourney

“You’re lucky I keep this roof over your heads,” he’d say and chortle. He also said it all the time while leaning back on his worn-out recliner. It was his favorite thing in the world.

My mom, Jane, always nodded along. She was the kind of woman who avoided conflict at any cost. She wasn’t raised in the 1950s, but her upbringing had been different from ours. Staying quiet had become almost an art form for her.

As her kids, my siblings (Chloe, Lily, and Anthony) and I could see that she desperately wanted to speak up but didn’t. Meanwhile, we surely didn’t consider him “the king of the castle” or a “real man,” which were other phrases Jeff used to describe himself.

A woman at a dinning table | Source: Midjourney

A woman at a dinning table | Source: Midjourney

Yes, he paid all the bills while we were growing up, and we were thankful. But that wasn’t an excuse to treat our mother like a servant and think he was better than the rest of us.

We had tried for years to get Mom to leave him to no avail.

Eventually, we all moved out of their house as we reached adulthood, but my sisters and I continued to visit Mom often. Anthony lived on the other side of the country, but he checked in every other day.

A man on the phone | Source: Midjourney

A man on the phone | Source: Midjourney

Still, we worried about her.

I felt that our visits weren’t enough to truly know what was going on in that house. I often sat alone in my apartment and wondered if Mom would ever leave this man and if there was something he could do to finally make her snap out of her proverbial shackles.

Yes, this is where it gets good.

This year, Jeff simply went too far. For days leading up to Mom’s birthday, he wouldn’t stop bragging about the “special gift” he’d picked out for her.

A man on a reclining chair | Source: Midjourney

A man on a reclining chair | Source: Midjourney

“This one’s going to knock her socks off,” he said over dinner at their house, grinning like a buffoon.

I wanted to believe him. Maybe he had finally decided to treat her with the respect she deserved. But deep down, I knew better. Jeff was Jeff, and people like him never changed.

My mom’s birthday arrived, and of course, my sisters and I were there, sitting in the living room. Jeff had a twinkle in his eyes, and I knew Mom had hope in hers.

Three sisters with presents in their hands | Source: Midjourney

Three sisters with presents in their hands | Source: Midjourney

After she opened our presents, my stepdad handed her a huge, beautifully wrapped package. He was smiling, and my mom’s face lit up as she carefully untied the ribbon.

“Oh, Jeff, you didn’t have to,” she said softly.

“Yes, I did. Go on. Open it,” he urged, leaning forward in his chair.

She unwrapped the box slowly, savoring the moment… until she saw what was inside— toilet paper. 12-pack. Four-ply. Jumbo rolls.

A woman smiling with a big present | Source: Midjourney

A woman smiling with a big present | Source: Midjourney

Mom blinked in confusion.

“It’s so soft. Just like you!” Jeff declared, slapping his knee and cackling. “And look, four-ply, to represent your four kids. Perfect, right?”

Mom let out a nervous laugh, but I could see her eyes glistening. My sisters and I exchanged a look. This wasn’t just a bad joke; it was cruel.

We’d had enough. We had to do something.

A woman looking angry | Source: Midjourney

A woman looking angry | Source: Midjourney

***

Two days later, our plan began to take shape. Jeff loved two things: being the “big man” and free food. So, we invited him to a “family dinner” at the Chinese restaurant he always raved about.

Chloe, my youngest sibling, was the one who planted the idea.

“We’ll do it in his favorite place. He won’t suspect a thing,” she said, smirking.

Lily, being the eldest and most practical, raised an eyebrow. “And what happens after?”

“Oh, don’t worry,” Chloe replied. “We’ll handle it.”

A woman smiling | Source: Midjourney

A woman smiling | Source: Midjourney

We set the date and made sure to hype it up, so Jeff wouldn’t miss it.

“Dinner’s on us this time,” Chloe told him sweetly

Jeff puffed out his chest. “Well, it’s about time someone else paid for once. I’m glad that being out of the house has finally opened your eyes to how great you fared because of me!”

We rolled our eyes internally.

The restaurant was bustling that night. Shiny red lanterns hung from the ceiling, giving the space a nice reddish glow.

Chinese restaurant | Source: Midjourney

Chinese restaurant | Source: Midjourney

The food from other tables smelled delicious, and I could tell Jeff was hungry as we sat down at our table.

“When are your mom and Lily getting here?” he asked, wrinkling his nose toward the front door.

“Don’t worry. They’ll be here soon. How about we order food anyway?” I suggested, nodding towards Chloe.

She agreed and started rattling off things she wanted, things we specifically planned to order: Szechuan beef, Kung Pao chicken, and the spiciest mapo tofu on the menu.

Chinese menu | Source: Midjourney

Chinese menu | Source: Midjourney

Jeff ordered his usual, but I knew what we had in mind would still work.

Each dish came out looking like a masterpiece of fiery reds and deep browns, garnished with fresh herbs and enough chili to make a grown man cry.

Chloe’s eyes twinkled as the waiter finished arranging everything on the table.

“Jeff, you can handle spicy, right?” she asked, pretending to be concerned.

A woman smiling at Chinese restaurant | Source: Midjourney

A woman smiling at Chinese restaurant | Source: Midjourney

Jeff stayed silent for a second, stumped, then nodded quickly. “I didn’t realize you gals wanted to share everything. Of course, I can eat anything. Nothing is ever too spicy for a real man.”

I chimed in with, “Be careful with these, though. They’re pretty hot.”

I just knew my words would make him mad.

“Don’t be ridiculous, Amelia,” Jeff scoffed and took his chopsticks to skewer a piece of beef straight into his mouth.

A man looking serious at a Chinese restaurant | Source: Midjourney

A man looking serious at a Chinese restaurant | Source: Midjourney

At first, he gave out an exaggerated moan, to “prove his manliness,” but soon, his face turned redder than the lanterns above us. Sweat beaded on his forehead as he chewed and breathed through his nose.

“Everything alright?” Chloe asked, again faking worry.

“Yes, yes,” he lied through his full mouth. “This is good stuff.”

I was sure Jeff wouldn’t grab more after gulping down an entire glass of Coke, but Chloe and I began eating in earnest.

“Oh, it’s not so spicy after all,” Chloe commented, smiling sugary-sweet. She was baiting him.

A woman smiling with chopsticks in her hand | Source: Midjourney

A woman smiling with chopsticks in her hand | Source: Midjourney

I nodded, grabbing more.

Not to be outdone, Jeff began to eat more. He was breathing roughly now, but when we asked if he was alright, he simply said, “This really clears the sinuses, gals.”

Still, his fingers went up and snapped at the waiter to bring him more Coke.

Chloe leaned over and whispered, “He’s going to feel that later.”

“Oh, definitely,” I whispered back, grinning conspiratorially.

A woman smiling | Source: Midjourney

A woman smiling | Source: Midjourney

***

While Jeff was busy showing off his “macho” tolerance for heat, Mom and Lily were busy back at the house with a rented U-Haul and movers.

They worked quickly to load up Mom’s belongings, such as clothes, keepsakes, her favorite chair, and even the toaster. I told them to take the things Mom had given Jeff over the years by saving up when she could: the recliner and his specialty tools.

A truck and workers loading boxes | Source: Midjourney

A truck and workers loading boxes | Source: Midjourney

But the pièce de résistance was Chloe telling them to remove every single roll of toilet paper in the house.

***

Jeff was still red when we left the restaurant, and he was grumbling about Mom and Lily being no-shows. So I just suggested going to the house to see if anything had happened.

When we arrived, everything was ready. The truck had already left. Meanwhile, Mom and Lily were hiding in the garage.

Jeff walked in with Chloe and me right behind him. He barely made it two steps into the living room before he froze.

A dimly lit living room | Source: Midjourney

A dimly lit living room | Source: Midjourney

“Where’s my recliner?” he barked, scanning the empty spot.

“Gone,” Chloe piped in casually, tilting her head. “Mom took what’s hers.”

Jeff turned to us and his face reddened again, but before he could say another word, his stomach gurgled loudly. He doubled over slightly, clutching his gut.

“Oh, man, I think that spicy food—” He paused, looking around frantically.

A man holding his stomach | Source: Midjourney

A man holding his stomach | Source: Midjourney

“Is something wrong, Jeff? I hope it wasn’t the food,” I said, blinking innocently.

He stared daggers at me before bolting down the hall. Moments later, we heard the bathroom door slam.

Lily and Mom appeared out of their hiding spot right in time to hear the sound of Jeff panicking. “What the hell? Where’s all the toilet paper?!” he yelled.

I couldn’t hold it in anymore.

“We took that along with the recliner!” I shouted, laughter bubbling up. “After all, it also belonged to Mom!”

A woman laughing | Source: Midjourney

A woman laughing | Source: Midjourney

“WHAT?” he shouted back.

It seemed like he wasn’t getting it, so Mom stepped closer to the bathroom door. “I’M LEAVING YOU, JEFF! And I took what was mine,” she exclaimed firmly. “Including my dignity.”

Jeff groaned loudly from behind the bathroom door. “You can’t just leave me like this!” he yelled.

“WATCH ME!” Mom replied, adding, “Not that you can right now, but enjoy staying in the bathroom all night!”

A woman next to a closed door | Source: Midjourney

A woman next to a closed door | Source: Midjourney

My sisters and I stared at each other, giggling.

Jeff groaned, and there were other unsavory sounds, which I took as our cue to leave. “Let’s go, Mom,” I said.

She nodded and walked out, thanking us.

***

The next day, Jeff tried to call her. Over and over again, he left voicemails full of fake apologies and pitiful excuses.

“Jane, come on, be reasonable! You can’t just run off like this!” he begged.

A man using a phone | Source: Midjourney

A man using a phone | Source: Midjourney

But Mom didn’t answer or call back.

Instead, Chloe had a better idea.

On his birthday, we sent Jeff a little gift. A jumbo pack of toilet paper, wrapped just as carefully as the one he’d given Mom.

Attached was a handwritten note that read: “For a real man.”

Rolls of toilet paper on a porch | Source: Midjourney

Rolls of toilet paper on a porch | Source: Midjourney

Mom moved in with Lily, a temporary arrangement where we all helped while she found a job. Anthony was delighted to learn about what we had done and wished he was there, too.

From what I hear, Jeff’s still complaining to anyone who’ll listen. But Mom is finally living her life without his control, and we couldn’t be prouder.

A happy woman | Source: Midjourney

A happy woman | 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.

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