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.

Entitled Couple Took My Premium Seat on the Plane – I Taught Them a Lesson and Turned It into a Profit

When I went out of my way to get one of the best seats on my flight, I didn’t expect to be swindled out of it by a manipulative couple. But what they didn’t know was that they messed with the wrong person, and in the end, I was the victor!

As soon as I settled into my aisle seat, feeling quite pleased with the extra legroom I had carefully selected for this long flight, I noticed a couple approaching. Little did I know that my interaction with them would lead to me teaching them an important lesson. Here’s my tale that can teach you how to stand up for yourself against bullies. Read on…

A woman at the airport | Source: Midjourney

A woman at the airport | Source: Midjourney

The woman who approached me was in her late thirties, dressed in a designer outfit that screamed wealth. But her expression was anything but pleasant. Her husband, tall and broad-shouldered, walked slightly behind her with an air of arrogance that matched her demeanor.

They stopped right next to me, and the woman’s eyes zeroed in on my seat. Without so much as a polite greeting and while exuding entitlement, she rudely demanded, “You need to switch seats with me. I accidentally booked the wrong seat, and I refuse to sit away from my husband.”

A mean couple trying to swindle a premium airplane seat | Source: Midjourney

A mean couple trying to swindle a premium airplane seat | Source: Midjourney

I blinked, taken aback by her tone. She spoke as if her mistake was somehow MY problem to fix! I glanced at her boarding pass, which confirmed my suspicion. It was a middle seat in row 12, not even close to the premium one I had chosen!

When I didn’t immediately comply, the woman rolled her eyes dramatically.

“Come on, it’s just a seat. YOU don’t need all that space,” she scoffed dismissively at my hesitation, her tone dripping with condescension.

A rude and arrogant woman on a plane | Source: Midjourney

A rude and arrogant woman on a plane | Source: Midjourney

Her husband, standing behind her with his arms crossed, smirked as he added, “Yeah, be reasonable. We need to sit together, and you don’t really need to be up here, do you?”

The audacity of their request left me momentarily speechless. They were clearly arrogant and hadn’t even bothered to ask nicely. They just assumed I would give in to their demands. I could feel the other passengers’ eyes on us, some curious, others sympathetic.

I took a deep breath, weighing my options. A confrontation wasn’t something I wanted to deal with, especially not at the start of a six-hour flight.

An upset woman sitting in her seat | Source: Midjourney

An upset woman sitting in her seat | Source: Midjourney

“Alright,” I said with as much calm as I could muster. Standing up, I handed over my boarding pass while trying hard to hide my irritation. “Enjoy the seat,” I told them without meaning it.

The woman snatched the ticket from my hand with a satisfied smirk. She muttered something under her breath about people in premium seats being “So selfish.” Her husband supported her by saying, “Someone like her doesn’t even need it.”

A happy couple sitting on a plane | Source: Midjourney

A happy couple sitting on a plane | Source: Midjourney

As I made my way toward the back of the plane, where her assigned seat was, I could feel my blood boiling. But I wasn’t one to make a scene. I had a better idea. Just as I approached row 12, a flight attendant, who had been watching the whole exchange, intercepted me.

She leaned in, her voice low as she whispered, “MA’AM, YOU DO REALIZE THIS WAS A SCAM, RIGHT? THEY TRICKED YOU OUT OF YOUR BETTER SEAT! THEY’RE BOTH MEANT TO BE IN ROW 12!”

I smiled at her, the anger simmering down to a cool resolve. “I know. But I’m about to turn the tables.”

A woman talking to a flight attendant | Source: Midjourney

A woman talking to a flight attendant | Source: Midjourney

“I actually have a little trick up MY sleeve. Don’t worry, I’ve got this,” I said as I winked.

The flight attendant raised an eyebrow, but she didn’t press further as she quickly put two and two together and tried stifling a laugh. She directed me to my new seat. So, as soon as I reached my middle seat and sat down, I started forming my plan.

The premium seat had been booked using my frequent flyer miles, and with that came certain privileges that most passengers wouldn’t be aware of. I knew exactly what to do to teach those two bullies a lesson they’d never forget…

A woman plotting while sitting in her seat | Source: Midjourney

A woman plotting while sitting in her seat | Source: Midjourney

My middle seat in row 12 wasn’t close to being as comfortable as the premium one I had given up, but I knew it would all be worth it. I allowed the mean couple to enjoy the seat and think they’d won.

About an hour into the flight, when the cabin had settled into a comfortable hum of quiet conversations and the occasional clink of glasses, I signaled for the flight attendant who had spoken to me earlier. She approached, and I asked to speak with the chief purser.

A flight attendant talking to a passenger | Source: Midjourney

A flight attendant talking to a passenger | Source: Midjourney

She nodded with a knowing smile and disappeared, returning moments later with a woman who exuded authority.

“Good afternoon, ma’am. I understand there was an issue with your seating,” the chief purser said, her voice professional but warm.

I explained my situation calmly, emphasizing how I had been moved from my premium seat due to the couple’s deception. The purser listened carefully, her expression serious.

When I finished, she nodded and said, “I appreciate you bringing this to my attention. Please give me a moment.”

A chief purser talking to a passenger | Source: Midjourney

A chief purser talking to a passenger | Source: Midjourney

I noticed a few passengers paying close attention to what was happening. They must have figured that I was retaliating in some way and didn’t want to miss anything. They hilariously kept throwing glances in my direction and at the departing purser.

When the head stewardess walked away, she left me wondering what my next move should be. A few minutes later, she returned, but instead of an apology, she offered me a choice.

A chief purser talking to a passenger | Source: Midjourney

A chief purser talking to a passenger | Source: Midjourney

“Ma’am, you have two options. You can either return to your original seat, or we can compensate you for the inconvenience with a significant amount of airline miles, equal to upgrades on your next three flights.”

I pretended to consider it, but I already knew what I wanted. “I’ll take the miles,” I said, smiling inwardly at the thought of the extra benefits this would bring. I knew fully well that the miles were worth far more than the price difference between premium and economy on this flight.

A woman thinking | Source: Midjourney

A woman thinking | Source: Midjourney

The purser smiled and made a note on her tablet. “It’s done. And as a token of goodwill, we’ve upgraded your next flight to first class.”

“Thank you,” I replied, genuinely pleased. As she walked away, I settled back into my seat, a sense of satisfaction washing over me. I knew the couple up front had no idea what was coming.

The flight continued without incident until we began our descent. That’s when I noticed a flurry of activity around row 3, where the couple sat. The chief purser, accompanied by another flight attendant had made their way to them, their expressions serious.

A chief purser and a flight attendant walking together | Source: Midjourney

A chief purser and a flight attendant walking together | Source: Midjourney

“Excuse me, Mr. Williams and MISS Broadbent,” the purser began, her tone no longer friendly. She pronounced the woman’s title with emphasis, making it clear to all aboard that the couple weren’t even married!

“We need to address an issue with your seats,” she continued looking quite stern.

Broadbent’s smile faltered, and Williams looked genuinely puzzled.

“What do you mean?” she asked, her voice tinged with irritation.

Shocked passengers | Source: Midjourney

Shocked passengers | Source: Midjourney

The purser glanced at her tablet before continuing. “We’ve been informed that you manipulated another passenger into switching seats with you, which is a violation of our airline’s policy. This is a serious offense.”

The color drained from the woman’s face, and she stammered, “But… but we didn’t do anything wrong! We just asked to switch seats!”

“Unfortunately,” the purser interrupted, “we have clear reports of your behavior. Upon landing, you’ll need to go with security for further questioning.”

A serious chief purser talking to passengers | Source: Midjourney

A serious chief purser talking to passengers | Source: Midjourney

All the passengers had wide eyes as they absorbed all the drama!

“Also, lying about being married when you are not to manipulate other passengers, is problematic in its own way. Additionally, due to this breach, you will be placed on our airline’s no-fly list pending an investigation,” the purser continued.

Williams opened his mouth to protest, but no words came out. The flight attendants, already poised to act, ushered them out of their seats and toward the back of the plane. As they were escorted, Broadbent felt the need to defend herself.

An angry passenger shouting on a plane | Source: Midjourney

An angry passenger shouting on a plane | Source: Midjourney

“I might not be his wife now, but I will be in a few months! He is going to divorce his wife to be with me!” she yelled frantically.

A collective shock settled among all of us as we realized the two were having an affair!

The crew took them where they would be the first to be escorted off by airport security.

As I gathered my belongings after landing, I couldn’t resist glancing at the couple one last time. Their smug expressions were gone, replaced by a mix of anger and humiliation.

A happy woman gathering her luggage before disembarking from a plane | Source: Midjourney

A happy woman gathering her luggage before disembarking from a plane | Source: Midjourney

They had lost more than just a seat as they were now facing consequences that would follow them long after this flight. Walking through the airport, I couldn’t help but smile to myself.

In my 33 years of life, I’ve realized that sometimes, getting even isn’t about making a big spectacle to get your way; it’s about patiently watching those who think they’ve won realize just how badly they’ve lost!

A pleased woman leaving the airport | Source: Midjourney

A pleased woman leaving the airport | Source: Midjourney

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