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 ruined my birthday because of her fixation on diet culture — I didn’t let it go unnoticed

Madeleine’s birthday takes an unexpected turn when her sister’s diet obsession turns the celebration upside down. Determined not to ruin her special day, Madeleine plans a bold move and gives Fiona a taste of her own medicine. Will Madeleine’s daring response save the day or create even more chaos?

“Fiona, can you come over to help with the birthday party?” I asked, sitting comfortably on my plush sofa, my phone pressed to my ear.

“Sure, Madeleine,” Fiona replied cheerfully. “What do you need me to do?”

“Decorations and food,” I said, relief washing over me. “I could really use an extra pair of hands!”

“No problem,” she said. “I’ll take care of it.”

I smiled, feeling a weight lift off my shoulders. “Thanks, Fiona! What would I do without you? I’ll send you some money for the decorations, drinks, and a simple BBQ.”

“Got it. I’ll make sure everything looks perfect,” Fiona assured me.

After hanging up, I quickly transferred the money to her account.

I trusted Fiona with the decorations; she had an eye for detail and always made everything look beautiful. I texted her the list of things we needed and told her I’d leave the keys under the doormat.

“Hey, sweetheart, are we all set for the party?” my fiancé, Albert, asked as I sent my last text to Fiona.

“Almost,” I said, standing up and giving him a reassuring smile. “Fiona’s handling the decorations and food. We just need to pick up some cups and plates from the supermarket.”

“Didn’t we already have enough?” he asked, a little puzzled.

“I thought so, too,” I admitted, shaking my head. “But it turns out we’re short. I don’t want to risk running out during the party.”

“Good call,” Albert said, grabbing the car keys. “Let’s go then. Better to get this done early.”

As we drove to the supermarket, I felt both excited and nervous. Hosting a party always brought these feelings, but having Fiona and Albert helping made everything easier.

I thought about the backyard and how I wanted it to look festive and welcoming. Fiona’s decorations would be perfect, and the BBQ would keep everyone happy and full.

“Are you okay?” Albert asked, glancing at me as he drove.

“Yeah,” I replied, smiling. “Just thinking about how everything will turn out.”

“It’ll be great, Madeleine,” he said, squeezing my hand. “We’ve got this.”

We arrived at the supermarket and quickly gathered the cups and plates we needed. As we loaded them into the car, I felt a sense of accomplishment.

Everything was coming together.

“And we’re back!” I called out as Albert and I walked into the backyard, carrying the cups and plates. But my smile quickly turned to shock as I took in the scene before me.

The table was filled with an array of vegetables, rice cakes, and several containers of 0% yogurt, which was essentially yogurt with no fat or sugar.

And instead of a proper cake, there was half a watermelon with candles stuck into it.

My heart sank. This wasn’t what I had in mind at all.

I turned to Albert, whose eyes widened in disbelief. “What’s going on here?” he asked, clearly puzzled.

“I don’t know,” I said, confused.

I spotted Fiona arranging the table and quickly walked over to her, pulling her aside. “Fiona, what happened to the BBQ??” I asked, trying to keep my frustration in check.

“Well, it wasn’t a good idea considering your size, so I chose better options!” she said matter-of-factly.

I was shocked.

I come from a “bigger” family and have learned to love myself as I am. However, Fiona has always struggled with her self-image, trying hundreds of diets but never sticking to any of them.

I felt my cheeks flush with anger, knowing she’d done it because of her diet obsession! But I swallowed my anger as causing a scene wouldn’t help anything. The guests were starting to arrive, and I didn’t want to ruin the evening for everyone.

“So yeah, what was I saying? Yep, I just thought healthier options would be better for you, Madeliene,” she said, looking at me as if she had done me a favor.

“Fiona, this is a party! People expect to have fun and enjoy good food!” I almost snapped.

“I just thought this would be better,” she shrugged as if it was no big deal.

Taking a deep breath, I decided I had to fix this. I walked over to Albert, who was also puzzled by the spread.

“Albert, we need to order some normal food. The guests will be here any minute,” I said.

“Alright, I’ll call the pizza place and get some burgers delivered, too. We can’t let this ruin the evening.”

“Thank you,” I said, grateful for his quick thinking.

As Albert made the calls, I tried to mingle with the arriving guests, keeping a smile on my face despite my frustration. Everyone was polite, but I could see the confusion in their eyes as they looked at the food.

“What’s going on with the food?” one of our friends asked.

“Just a little mix-up,” I said with a forced laugh. “We’ve got some more food coming soon.”

Soon, Albert came back, giving me a reassuring nod. “Food’s on its way. Should be here in about thirty minutes,” he whispered to me.

“Perfect,” I sighed. “Thank you, Albert.”

“Don’t worry, Madeleine,” he said, giving my shoulder a squeeze. “We’ll turn this around.”

With Albert’s reassuring nod, I felt a bit more at ease, knowing that more food was on its way. But I was starting to place the order for the BBQ when Fiona snapped.

“SORRY FOR BEING SUCH A TERRIBLE SISTER AND TRYING TO HELP YOU LOSE ALL THIS FAT!” she screamed, her voice echoing across the backyard. “KEEP STUFFING YOURSELF WITH BBQ, BUT DON’T EXPECT ME TO CHEER YOU UP WHEN YOUR FIANCÉ KICKS YOU OUT!”

The sudden outburst left everyone stunned. The guests looked around awkwardly, not sure what to do or say. I felt my face flush with embarrassment and anger!

“Fiona, will you please stop it?!” I said, pulling her aside again.

She glared at me, her eyes filled with frustration. “I was only trying to help you, Madeleine. You never listen!”

“Look, this is not the time or place for this,” I said, my hands shaking slightly. “We have guests here. Can we please talk about this later?”

“Everyone, let’s enjoy the evening. The food will be here soon, and we can all have a good time,” Albert announced, facing the guests. I could only feel grateful he was there to handle the situation with me.

Fiona crossed her arms, fuming, but she didn’t say anything further. I could see the guests shifting uncomfortably. I took a deep breath, trying to regain my composure.

“I’m sorry, everyone,” I said, addressing the crowd. “There was a bit of a misunderstanding, but it’s all sorted now. Please, make yourselves comfortable.”

With that, I turned and hurried inside to write a note for the delivery guy. “Please make sure to hand the order directly to me (Madeleine), not my sister,” I scribbled quickly, sticking the note on the front door.

The minutes dragged on as I anxiously awaited the arrival of the food. I kept glancing at the clock, hoping it would get there soon so we could move past the awkwardness. Finally, the doorbell rang.

I opened the door to greet the delivery guy, who handed me the bags filled with BBQ and other goodies.

“Thank you so much,” I said, taking the food from him.

“No problem,” he replied with a friendly smile.

Carrying the food back to the backyard, I took a deep breath. I was determined to salvage the evening, no matter what. But I was also going to teach Fiona a lesson about respecting boundaries and understanding what it means to truly help someone.

“Alright, everyone,” I announced, placing the BBQ and sides on the table. “The food is here! Let’s dig in and enjoy the evening!”

I began handing each guest a plate piled high with BBQ meat, salads, and sides. As I served, I made sure to keep my composure, smiling and chatting with everyone.

When I reached Fiona, I couldn’t help but feel a little mischievous. I stacked all the rice cakes and vegetables on a plate for her, making sure it was an impressive tower of the healthiest options available!

“Fiona,” I called out, drawing everyone’s attention. “I’ve got a special plate just for you!”

She looked up, surprised by the attention. As I handed her the plate, I couldn’t resist adding a little jab. “Here you go, Fiona. Make sure to stick with the healthy stuff. I wouldn’t want you to become unlovable by eating something unhealthy!”

Fiona’s face turned bright red. She stared at the plate, then looked at me with a mix of embarrassment and anger. “Thanks,” she mumbled, barely able to meet my eyes.

“Everyone, enjoy!” I said cheerfully as I moved on to serve the next guest.

I also kept an eye on Fiona. She stood off to the side, barely touching her plate. I could see the discomfort and humiliation on her face. Eventually, she put the plate down and made her way towards the exit.

“I’m leaving,” she said quietly as she passed by me, avoiding eye contact.

“Okay,” I replied, shrugging.

I watched her walk away, feeling a sense of relief.

The BBQ was a hit, and people came up to me, complimenting the food and the decorations. It was exactly the kind of evening I had hoped for despite the rocky start. Most importantly, my “sweet” sister received a taste of her own medicine.

What would you have done?

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