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 MIL Left the House Every Thursday & Returned Smelling Terribly — I Went Pale When I Discovered Why

They say you never really know someone until you’ve lived with them. I thought I knew my mother-in-law, but everything changed when I decided to follow her. What I uncovered wasn’t just a secret; it was a ticking time bomb that threatened the peace of our home.

I used to think my life was predictable, with its comforting routine. I worked as a freelance graphic designer, which gave me the flexibility to be home most days while still bringing in a decent income.

A woman working on her laptop from home | Source: Midjourney

A woman working on her laptop from home | Source: Midjourney

Xander, my husband, worked long hours at his law firm, so I often had the house to myself. It was peaceful until my mother-in-law, Cordelia, moved in three months ago.

After her husband passed away, she called us one night, her voice trembling.

“Olive, dear… I don’t know how to do this on my own,” she’d sobbed over the phone. “The house is so empty, so lonely… I just need to be around my family.”

An extremely sad senior woman talking on her phone | Source: Midjourney

An extremely sad senior woman talking on her phone | Source: Midjourney

I glanced at Xander, and he nodded, looking concerned. We agreed to let Cordelia move in; it felt like the right thing to do for a grieving woman who’d just lost her partner of 40 years. But from the start, something felt off.

Cordelia had always been a little strange, but now her behavior was unpredictable. Every Thursday, she would leave early in the morning and return late in the evening, her clothes carrying a terrible stench: something rotten and damp, like decay. It lingered, clinging to the air and making me question what she was really up to.

A woman looks thoughtful and curious while sitting at home | Source: Midjourney

A woman looks thoughtful and curious while sitting at home | Source: Midjourney

“Mom, where were you today?” Xander asked her one Thursday evening as she shuffled into the kitchen, her eyes avoiding ours. I stood by the stove, pretending to stir a pot of soup, trying not to wrinkle my nose at the smell.

“Oh, just out with some old friends,” she said, waving a hand dismissively, her smile tight and unconvincing.

A senior woman forces a smile while looking at someone | Source: Midjourney

A senior woman forces a smile while looking at someone | Source: Midjourney

“Every Thursday?” I asked, keeping my tone casual. “That must be some social circle.”

She glanced at me, her eyes lingering a moment too long, then shrugged. “We like to meet regularly. It’s good for the soul, you know, catching up with old friends.”

But that smell — it was like she’d been crawling through a sewer. The scent lingered long after she’d passed, a pungent blend of garbage and something wet and decayed. I could feel my curiosity gnawing at me, the way you can’t help but poke at a sore tooth.

A curious woman standing in the kitchen and looking at someone | Source: Midjourney

A curious woman standing in the kitchen and looking at someone | Source: Midjourney

One Wednesday night, I couldn’t take it anymore. “Xander,” I whispered, nudging him awake. “Are you seriously buying that story?”

He blinked sleepily. “What story?”

“Your mom’s ‘out with old friends’ story,” I replied. “Every Thursday? And that smell… it’s not normal.”

He sighed. “Maybe she’s just grieving in her own way, Olive. People cope differently.”

I felt my jaw tighten. “And what way is that? Dumpster diving?”

He chuckled softly, half-asleep, “Let it go, love. It’s probably nothing.”

A man chuckles softly while lying in bed at night | Source: Midjourney

A man chuckles softly while lying in bed at night | Source: Midjourney

But it didn’t feel like “nothing.” It felt like a secret, and I needed to know.

The next Thursday, I called in sick and decided to follow her. I waited by the window, peeking through the blinds like some kind of amateur detective. Cordelia left the house at her usual time, dressed in her oversized coat, clutching her handbag tightly.

I kept a safe distance as she walked down the street, turning left at the end and then another left into an alley I didn’t even know existed. My heart pounded in my chest as I tailed her.

A woman is out on the street, looking at someone | Source: Midjourney

A woman is out on the street, looking at someone | Source: Midjourney

She stopped at the corner and looked around like she was checking for someone or something.

“Where are you going, Cordelia?” I whispered, more curious than ever.

I was expecting something harmless, maybe even laughable, like an old ladies’ knitting club or maybe a bingo night in a creepy basement. But what I found inside was nothing like that.

Cordelia didn’t meet up with friends. Instead, she made her way through the shadiest part of town, slipping into an old, run-down building that looked like it could collapse at any moment.

A senior woman standing outside an old building | Source: Midjourney

A senior woman standing outside an old building | Source: Midjourney

I hesitated outside, the walls covered in graffiti and the windows boarded up, but I took a deep breath and followed her inside. The air was thick with smoke, the kind that sticks to your skin, and the room was filled with the low hum of murmurs and distant laughter.

That’s when I saw it: a hidden, illegal casino tucked away in the back, reeking of stale smoke and the sour smell of desperation. The dimly lit room was filled with flashing lights and the sounds of poker chips clinking filled the air.

Stacks of poker chips on a table | Source: Pexels

Stacks of poker chips on a table | Source: Pexels

And there, in the middle of it all, was my mother-in-law. Not just “hanging out with friends,” but gambling away every penny she could get her hands on, her eyes fixed on the cards in front of her, her hands trembling with each bet she placed.

I stayed in the shadows, barely breathing, watching her play hand after hand. She looked different, haggard, almost like she was wearing the weight of every decision she’d ever made. Her lips were moving, but I couldn’t hear what she was saying over the noise.

A grayscale photo of a senior woman sitting in a casino with gambling chips lying on her table | Source: Midjourney

A grayscale photo of a senior woman sitting in a casino with gambling chips lying on her table | Source: Midjourney

I saw her lose money, win a little, then lose it all again. She seemed almost possessed, her fingers shaking as she reached for the chips, her face lined with a mixture of desperation and obsession.

I wanted to pull her out of there, to grab her by the arm and drag her home, but I couldn’t move. I felt frozen, glued to the spot. I needed to see how far she would go. She didn’t leave until late in the evening, and when she finally did, she looked exhausted.

A senior woman looks exhausted while sitting in a casino | Source: Midjourney

A senior woman looks exhausted while sitting in a casino | Source: Midjourney

Her eyes were glazed over, and her shoulders slumped like she was carrying the weight of her losses on her back.

I waited until she turned the corner before I followed, keeping my distance. As we walked back, I felt a wave of anger and pity twisting in my stomach. What had she gotten herself into? And why hadn’t she told us?

The next morning, I couldn’t hold it in any longer. At breakfast, I set my coffee cup down a little too hard. “Cordelia, where were you yesterday?” I asked, my voice sharper than I intended.

A woman looks serious while standing in the kitchen and looking at someone | Source: Midjourney

A woman looks serious while standing in the kitchen and looking at someone | Source: Midjourney

She barely looked up from her cereal. “With friends, like I told you.”

“Stop lying, Cordelia,” I snapped. “I followed you. I know where you were.”

Her spoon clattered against the bowl, and she went pale. “You… you followed me?”

Xander looked between us, confused. “What’s going on?”

“She wasn’t with friends, Xander,” I said, my gaze fixed on her. “She was at an illegal casino, gambling. And from the looks of it, she’s been doing it for a while.”

A senior woman gambling in a casino | Source: Midjourney

A senior woman gambling in a casino | Source: Midjourney

Cordelia’s face crumpled, and she broke down. “I… I’m sorry,” she sobbed. “I’ve lost everything… everything. I had nowhere else to go. That’s why I begged you to let me stay. I was ashamed, and I didn’t know how to tell you…”

Xander’s face turned a deep shade of red. “You mean to tell me you’ve been lying to us this whole time? Using us?”

“I didn’t mean to!” she cried. “I didn’t know how to stop. I thought maybe… maybe I could win it all back.”

A grayscale photo of a senior woman looking sad and desperate | Source: Midjourney

A grayscale photo of a senior woman looking sad and desperate | Source: Midjourney

I felt a pang of guilt, but it was overshadowed by the anger boiling inside me. “You’ve been draining us, Cordelia. We took you in because we cared, not so you could feed your addiction.”

She looked at me, her face streaked with tears. “I know, I’m so sorry. I promise I’ll change. Just… don’t throw me out. Please.”

That night, Xander and I lay in bed, unable to sleep. “We have to do something,” I whispered. “We can’t just let her keep doing this.”

Xander sighed deeply. “What do you suggest, Olive? Tough love?”

A man looking at his wife while sitting in bed at night | Source: Midjourney

A man looking at his wife while sitting in bed at night | Source: Midjourney

I nodded. “Exactly. If she’s not going to stop on her own, then we’ll have to make her stop.”

The following Thursday, I handed her a large sum of cash, more than she had seen in one place since she’d moved in with us. Her eyes widened, and for a moment, I saw that familiar spark of greed.

“Go ahead,” I said, forcing a smile. “Take this and do whatever you want with it.”

A woman forcing a smile while looking at someone | Source: Midjourney

A woman forcing a smile while looking at someone | Source: Midjourney

She hesitated for just a second before snatching the money and stuffing it into her purse.

“Thank you, Olive,” she murmured, her voice shaking, but she didn’t meet my eyes. And then she was gone, practically running out the door.

Xander stood behind me, his arms crossed. “Are you sure about this?”

“Trust me,” I replied. “She won’t get far.”

Earlier that day, I had made a few calls, and by the time Cordelia reached the casino, the place was swarming with undercover cops. The raid went down right as she was about to hand over the cash.

Two cops standing in a casino | Source: Midjourney

Two cops standing in a casino | Source: Midjourney

I wasn’t there to see it, but I could imagine the look on her face: shock, maybe a little betrayal, as they caught her red-handed, along with the owners of the illegal casino.

That evening, the phone rang. It was the police. “Mrs. Fields?” the officer said. “We have your mother-in-law in custody.”

“We know,” I replied calmly. “And we’re not bailing her out. You should know she’s been struggling with a gambling addiction. We want her to get help.”

A woman talking on her phone | Source: Midjourney

A woman talking on her phone | Source: Midjourney

The officer seemed taken aback but eventually agreed to include our statement in the report. The judge showed no mercy; Cordelia was sentenced to mandatory rehabilitation and a hefty fine.

Months later, when she was released from rehab, Cordelia looked different. She seemed smaller, more fragile. She stood in our doorway, wringing her hands.

“I’m so sorry,” she whispered, her voice raw. “I know I hurt you both, and I’m ready to make it right. I want to rebuild my life.”

A senior woman looks sad and ashamed | Source: Midjourney

A senior woman looks sad and ashamed | Source: Midjourney

Xander and I exchanged a look. He stepped forward, his expression soft but firm.

“We’re willing to give you another chance, Mom,” he said, “but on our terms. We’ve found you a modest apartment nearby. We’ll cover the rent, but only if you keep your word and attend your support group meetings.”

Cordelia nodded eagerly, tears in her eyes. “I will. I swear. Thank you… thank you for giving me a chance.”

As we watched her walk away to her new home, I couldn’t help but feel a flicker of hope mixed with the fear of another betrayal.

A woman looks hopeful and a bit fearful while standing outside her house and looking at something | Source: Midjourney

A woman looks hopeful and a bit fearful while standing outside her house and looking at something | Source: Midjourney

We’d done all we could, and the rest was up to her. The ball was in her court, and only time would tell if she could truly change.

But when Natasha starts to see a change in Marlene’s behavior, she begins to get worried about the old woman. Eventually, when the truth is revealed, Natasha doesn’t know what to do.

Two women cooking together | Source: Pexels

Two women cooking together | Source: Pexels

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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