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.

Son Leaves Mom in Wheelchair on the Street, Year Later Sees Her Coming to His House on Her Feet – Story of the Day

Wendy hoped her son, John, would care for her in her sunset years. But John left her alone on the street. He did not expect his mother to appear at his doorstep a year later, standing on her feet.

“Can’t talk now, mom! I’m with a customer. I might finally sell a house this year. I’ll call the neighbors to check up on you. But I’m sure it’s nothing. You must’ve sat on the pot too long. Ok. Gotta go. I’ll come in to check on you tonight.”

Wendy remembered the call with her son, John, the first time her legs went numb. She remembered the state of panic she was in when she called him for help. She remembered getting breathless, fearing she was going to die. But her son did not have time to help her despite living a few blocks away.

He didn’t remember to call the neighbors to check in on her or visit her that night. And he even failed to sell the house, or any house, for that entire year.

For illustration purposes only. | Source: Getty Images

For illustration purposes only. | Source: Getty Images

It had been a year since Wendy started feeling numbness in her legs. They stopped working all of a sudden as if they were paralyzed. Initially, the weakness in her legs lasted 10-15 minutes. She would wait it out by simply gathering herself and resting in the corner of the house until her legs came back to normal.

Eventually, the frequency of her legs going numb increased, until one day, when she had a fall and couldn’t get up. She cried for help, and luckily, the neighbors showed up. They informed John, who rushed in and took Wendy to the hospital.

Wendy was diagnosed with a rare nerve compression syndrome that caused numbness in her lower limbs. Her situation got complicated for over a year as she and John ignored her symptoms. And the injuries she sustained while falling made things worse.

Wendy was now in a wheelchair.

For illustration purposes only. | Source: Getty Images

For illustration purposes only. | Source: Getty Images

John drove Wendy to the hospital and back for the first month of her physiotherapy sessions, but nothing helped Wendy get better. Although Wendy was spending her money for the treatment, John was getting frustrated, driving her to and fro.

“I think you should give up, mom. How many times am I supposed to miss my meetings? You know I need to focus on selling houses, right?” Wendy would wipe her tears while listening to her son’s insensitive comments during their car rides.

‘But he’s my son. At least he’s there for me,’ Wendy would console herself.

Karma will always hit you back.

After the physiotherapy and medication did not improve Wendy’s condition, the doctors suggested she get an expensive surgery. Wendy had spent all her savings on her treatment. She asked John for help, but he refused.

“Do you know how much rent I pay for my house? I can’t afford it, but as a realtor, I need to have a lifestyle. Who would buy a house from someone who lives in a small house?” John explained to Wendy.

For illustration purposes only. | Source: Getty Images

For illustration purposes only. | Source: Getty Images

One day, John received a call from Wendy’s neighbors saying she was at the hospital for surgery. John did not know about any surgery, but he drove to the hospital.

He reached Wendy’s room and saw her sitting on her bed, crying while a group of doctors spoke to her. The primary doctor noticed John and came out of the room and said, “Are you Mr. John Matthews, her son?” John nodded.

“Where have you been? We waited for someone next of kin, but since no one arrived, we decided to deliver the news to Wendy directly.”

“What news?”

“Mr. Matthews, your mother’s surgery did not give the expected results. We still haven’t noticed any significant movement in her legs. And we can’t be sure when we will see a change. We’ll have to wait and watch for now. Wendy has already signed the discharge formalities and is free to go.”

For illustration purposes only. | Source: Getty Images

For illustration purposes only. | Source: Getty Images

John feigned empathy for Wendy and consoled her. As he took her in the wheelchair towards his car, he asked her how she arranged for the money.

“I didn’t want to trouble you for any money, son, so I made the decision myself.”

“What decision, mom?”

“I sold the house.”

John stopped in his tracks, stunned.

“Remember Joanne? My friend from the old book club who moved to another city? She introduced me to her nephew, who wanted to buy a house in our area. Actually, they called and said they were coming here to visit me—”

“Are you kidding, mom? You sold the house? And for what, a failed surgery? You’re so selfish! You didn’t even think of me! It’s my house too, right? I was waiting on that house after—”

For illustration purposes only. | Source: Getty Images

For illustration purposes only. | Source: Getty Images

John stopped himself, but Wendy realized what he meant. She was hurt that all John cared about was his inheritance and did not care about her.

Wendy was wiping her tears when John got a call from a prospective customer. He walked away to answer it. After his call, he told Wendy he had an urgent meeting with his customer.

“Go, son. As I said, Joanne was coming to visit me. I’ll ask her to drop me at the nursing home, and I have already spoken to them about moving there.”

“You see, that’s what I’m talking about. I had no idea what you do—”

John was interrupted by another call. He shook his head with disgust at his mother and just took off. Wendy was quietly sobbing on the street near the parking lot, feeling alone and hurt.

For illustration purposes only. | Source: Getty Images

For illustration purposes only. | Source: Getty Images

A year had passed, and John hadn’t spoken with his mother. One morning, he heard a car pull up near his driveway. He wasn’t expecting visitors. He went out and saw a senior woman get out of the car. She stood outside the car, searching for something in the glove compartment.

“Can I help you, ma’am?” John asked, confused to see a stranger park outside his house.

When the woman turned around, John had the shock of his life. It was Wendy, and she was able to walk on her feet.

“Mom, oh my God! How are you?”

“Much better, son. I love every moment.” Wendy’s positive response took John aback, and he invited her to the house and offered her a glass of water.

John did not know how to interact with her. Wendy broke the ice and said, “Don’t look so gloomy, son. Look, I’m fine now. Remember when you left me all alone on the street after I was out after a failed surgery?” John turned pale as he recounted his behavior.

For illustration purposes only. | Source: Getty Images

For illustration purposes only. | Source: Getty Images

“Well! My friend Joanne and her nephew, Evan, arrived shortly after that. They were heartbroken seeing me all alone near the parking lot, so they took me with them instead of dropping me at the nursing home. Joanne had to leave the next day, but Evan offered me to stay with him in my old house. I mean, his house since he bought it from me.”

“He cared for me like a son and even found better doctors in another city. I was afraid of another surgery, but Evan was there by my side throughout. And miraculously, the surgery worked. Evan also paid for my knee replacement surgery. Not only can I walk, but I can also run like I used to when I was young.”

John was speechless. Although he was embarrassed, he did not like how Wendy praised a stranger. He snarled, “I get it. I was a horrible son. But if this Evan is so great, why are you even here?”

John heard another car pull up outside his house. A young man walked into his house.

For illustration purposes only. | Source: Getty Images

For illustration purposes only. | Source: Getty Images

“Oh, Evan. Great timing. We were just talking about you,” Wendy chuckled, greeting Evan.

“Excuse me. You can’t just enter my house like that.” John said, furiously pointing at Evan.

“Well, but I can enter MY house, can’t I?” Evan’s words confused John.

As it turned out, Evan owned the house Jonathan was living in. John was unaware since he only dealt with the agency that mediated all the transactions. Furthermore, John had skipped six months’ rent and evaded calls from the agency.

The agency notified Evan after John skipped rent for a couple of months. But Evan knew that John was struggling based on what he heard from Wendy, so he decided to go easy on John and asked the agency to back off, too.

But when Wendy learned about John’s antics, she realized that she couldn’t give him any more rope. She urged Evan to punish John for not paying the rent.

“Oh, I almost forgot, son!” Wendy reached into her bag. “Here is the eviction notice. You have 15 days.” Wendy handed John the documents and left with Evan.

For illustration purposes only. | Source: Getty Images

For illustration purposes only. | Source: Getty Images

John sat on his couch and held his head. He realized that his behavior had finally led to him hitting rock bottom.

What can we learn from this story?

  • Take care of your parents. Our parents sacrificed a lot to raise us; the least we can do for them in their old age is care for them. Wendy cared a lot for John even if he disrespected and hurt her. John never cared for Wendy when she needed him but still expected her house as an inheritance.
  • Karma will always hit you back. John always treated Wendy with disdain and disrespect. His bad karma finally hit back when his mother decided to help evict him from his house.

Share this story with your friends. It might brighten their day and inspire them.

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