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.

I Married a Widower with a Young Son – One Day, the Boy Told Me His Real Mom Still Lives in Our House

“My real mom still lives here,” my stepson whispered one night. I laughed it off, until I started noticing strange things around our home.

When I married Ben, I thought I understood what it meant to step into the life of a widower. He had been so devoted to his late wife, Irene, and he was raising their seven-year-old son, Lucas, all on his own.

A happy father-son duo | Source: Midjourney

A happy father-son duo | Source: Midjourney

I respected the deep love he still held for her, knowing it was tied to the memory of his first love and Lucas’ mother. I wasn’t here to replace her, just to create a new chapter for all of us.

The first few months as a family were everything I had hoped for. Lucas welcomed me warmly, with none of the hesitation I had feared. I spent hours playing games with him, reading his favorite bedtime stories, and helping him with schoolwork.

A woman helping a young boy with homework | Source: Midjourney

A woman helping a young boy with homework | Source: Midjourney

I even learned to make his favorite mac and cheese exactly how he liked it — extra cheesy with breadcrumbs on top.

One day, out of nowhere, Lucas started calling me “Mom,” and every time, Ben and I would catch each other’s eye with proud smiles. It felt like things were falling perfectly into place.

One night, after a cozy evening, I was tucking Lucas into bed. Suddenly, he looked up at me, his eyes wide and serious. “You know, my real mom still lives here,” he whispered.

A young boy lying in bed at night | Source: Midjourney

A young boy lying in bed at night | Source: Midjourney

I chuckled softly, running my fingers through his hair. “Oh, sweetheart, your mom will always be with you, in your heart.”

But Lucas shook his head, clutching my hand with an intensity that made my heart skip. “No, she’s here. In the house. I see her sometimes.”

A chill prickled at the back of my neck. I forced a smile, brushing it off as a child’s imagination running wild. “It’s just a dream, honey. Go to sleep.”

A woman forces a smile while sitting in her bed at night | Source: Midjourney

A woman forces a smile while sitting in her bed at night | Source: Midjourney

Lucas settled down, but I felt uneasy. I pushed the thought aside, telling myself he was just adjusting to a new family, a new normal. But as the days passed, small things around the house began to unsettle me.

For starters, I’d clean up Lucas’ toys, only to find them later exactly where I’d picked them up. Not just once or twice, but again and again.

A closeup of toy blocks scattered on the floor | Source: Pexels

A closeup of toy blocks scattered on the floor | Source: Pexels

And the kitchen cabinets — I’d rearrange them the way I liked, but the next morning, things were back in their old places, like someone was trying to undo my touch on the home. It was unnerving, but I kept telling myself it was just my mind playing tricks.

Then, one evening, I noticed something I couldn’t explain. I had moved Irene’s photograph from the living room to a more discreet shelf in the hallway. But when I came downstairs the next day, there it was, back in its original spot, perfectly dusted as though someone had just cleaned it.

A photo frame containing a woman's picture | Source: Midjourney

A photo frame containing a woman’s picture | Source: Midjourney

I took a deep breath and decided to discuss it with Ben. “Are you moving things around the house?” I asked one evening, trying to sound casual as we were finishing dinner.

Ben looked up, grinning as though I’d told a silly joke. “No, Brenda, why would I? I think you’re just imagining things.”

He laughed, but there was something in his eyes — a hint of discomfort or maybe reluctance. I couldn’t place it, but I felt an invisible wall between us.

A man laughs to hide his discomfort | Source: Midjourney

A man laughs to hide his discomfort | Source: Midjourney

A few nights later, Lucas and I were working on a puzzle on the living room floor. He was focused, placing the pieces with his little tongue poking out in concentration, when he suddenly looked up at me, eyes wide and sincere.

“Mom says you shouldn’t touch her things.”

My heart skipped a beat. “What do you mean, sweetie?” I asked, trying to keep my voice steady as I glanced toward the hallway.

A stunned woman | Source: Midjourney

A stunned woman | Source: Midjourney

Lucas leaned in, lowering his voice. “Real Mom. She doesn’t like it when you move her things,” he whispered, glancing over his shoulder like he expected someone to be watching us.

I sat frozen, trying to process what he was saying.

The way he looked at me was so serious, like he was sharing a secret he wasn’t supposed to. I forced a smile, nodded, and gave his hand a gentle squeeze. “It’s okay, Lucas. You don’t have to worry. Let’s finish up our puzzle, alright?”

A closeup shot of a child making a puzzle | Source: Pexels

A closeup shot of a child making a puzzle | Source: Pexels

But that night, as Ben and I lay in bed, my mind raced. I tried to tell myself it was just a kid’s overactive imagination. But each time I closed my eyes, I’d hear Lucas’ words, see the way he’d glanced nervously toward the hallway.

When Ben was finally asleep, I got up quietly, heading to the attic. I knew Ben kept some of Irene’s old things in a box up there. Maybe if I could see them and find out more about her, it would help me understand why Lucas was acting this way.

A closeup shot of a metal box | Source: Pexels

A closeup shot of a metal box | Source: Pexels

I climbed the creaky stairs, my flashlight slicing through the dark, until I found the box tucked in a corner, dusty but well-kept.

The lid was heavier than I expected, as though it had absorbed years of memories. I pulled it off and found old photos, letters she’d written to Ben, and her wedding ring wrapped carefully in tissue. It was all so personal, and I felt a strange pang of guilt going through it.

A wedding ring wrapped in a tissue lying on an old wooden table | Source: Midjourney

A wedding ring wrapped in a tissue lying on an old wooden table | Source: Midjourney

But there was something else. A few items looked freshly moved, almost as if they’d been handled recently. And that’s when I noticed it: a small door in the corner, half hidden behind a stack of boxes.

I froze, squinting at the door. I’d been in the attic a few times but had never noticed it. Slowly, I pushed the boxes aside and twisted the old, tarnished knob. It clicked, opening into a narrow room dimly lit by a small window.

A narrow room dimly lit by a small window in an attic | Source: Midjourney

A narrow room dimly lit by a small window in an attic | Source: Midjourney

And there, sitting on a twin bed covered in blankets, was a woman I recognized immediately from the photos. She looked up, her eyes wide.

I stepped back, startled, and stammered, “You… you’re Emily, Ben’s sister, aren’t you?”

Emily’s expression shifted from surprise to something else — a quiet, eerie calm. “I’m sorry. You weren’t supposed to find out this way.”

I couldn’t believe what I was seeing. “Why didn’t Ben tell me? Why are you up here?”

A woman is dumbfounded while standing in an attic | Source: Midjourney

A woman is dumbfounded while standing in an attic | Source: Midjourney

She looked down, smoothing the edge of her blanket. “Ben didn’t want you to know. He thought you’d leave if you found out… if you saw me like this. I’ve… I’ve been here for three years now.”

“Three years?” I could barely process it. “You’ve been hiding up here all this time?”

Emily nodded slowly, her gaze distant. “I don’t… go outside much. I prefer it up here. But sometimes, I get restless. And Lucas… I talk to him sometimes. He’s such a sweet boy.”

A woman sitting in an attic and looking at someone | Source: Midjourney

A woman sitting in an attic and looking at someone | Source: Midjourney

A chill ran through me. “Emily, what are you telling him? He thinks his mother’s still here. He told me that she doesn’t like it when I move things.”

Emily’s face softened, but there was a trace of something unsettling in her eyes. “I tell him stories sometimes. About his mother. He misses her. I think it comforts him to know she’s still… present.”

“But he thinks you’re her. Lucas thinks you’re his real mom,” I said, my voice breaking.

A shocked woman in an attic | Source: Midjourney

A shocked woman in an attic | Source: Midjourney

She looked away. “Maybe it’s better that way. Maybe it helps him to feel she’s still here.”

I felt my head spinning as I backed out of the room, closing the door behind me. This was beyond anything I could have imagined. I went straight downstairs, finding Ben in the living room, his face immediately full of concern when he saw me.

“Ben,” I whispered, barely holding it together. “Why didn’t you tell me about Emily?”

He went pale, his eyes darting away. “Brenda, I—”

A surprised man looking at someone | Source: Midjourney

A surprised man looking at someone | Source: Midjourney

“Do you realize what she’s been doing? Lucas thinks… he thinks she’s his real mom!”

Ben’s face fell, and he sank onto the couch, his head in his hands. “I didn’t know it had gotten that bad. I thought… I thought keeping her here, out of sight, would be best. I couldn’t leave her alone. She’s my sister. And after Irene passed, Emily wasn’t the same. She refused to get any help.”

I sat beside him, gripping his hand. “But she’s confusing Lucas, Ben. He’s just a child. He doesn’t understand.”

A woman looking kind and concerned | Source: Midjourney

A woman looking kind and concerned | Source: Midjourney

Ben sighed, nodding slowly. “You’re right. This isn’t fair to Lucas—or to you. We can’t keep pretending like everything’s fine.”

After a few moments, I whispered, “I think we should set up a camera, just to see if she’s really been leaving her room. To know for sure.”

Ben hesitated, but eventually, he agreed. We set up a small, hidden camera outside Emily’s door that night.

The next evening, after Lucas had gone to bed, we sat in our room, watching the footage. For hours, nothing happened. Then, just past midnight, we saw her door creak open.

A grayscale shot of an open attic door | Source: Midjourney

A grayscale shot of an open attic door | Source: Midjourney

Emily stepped into the hallway, her hair loose around her face, and stood there, looking at Lucas’ bedroom door.

Then Lucas appeared, rubbing his eyes, and walked toward her. Even on the grainy screen, I could see his little hand reaching for her. She knelt down, whispering something to him, her hand on his shoulder. I couldn’t hear the words, but I saw Lucas nod and say something back, looking up at her with that same, earnest expression.

A young boy standing in his room | Source: Midjourney

A young boy standing in his room | Source: Midjourney

I felt a wave of anger and sadness I couldn’t quite control. “She’s been… she’s been feeding his imagination, Ben. This isn’t healthy.”

Ben watched the screen, his face drawn and tired. “I know. This has gone too far. We can’t let her do this to him anymore.”

The next morning, Ben sat down with Lucas, explaining everything in simple terms. He told him that his Aunt Emily was sick, that sometimes her illness made her act in ways that confused people, and that his real mom wasn’t coming back.

A father talking to his young son | Source: Midjourney

A father talking to his young son | Source: Midjourney

Lucas was quiet, looking down at his little hands, and I could tell he was struggling to understand. “But she told me she’s my mom. You can’t send her away, Dad,” he murmured, his eyes filling with tears.

Ben hugged him tightly, his voice thick with emotion. “I know, buddy. But that was her way of trying to help you feel close to your mom. She loves you, just like we do. And we’re going to help her get better.”

A woman standing in an attic | Source: Midjourney

A woman standing in an attic | Source: Midjourney

Later that day, Ben arranged for Emily to see a doctor. The process was painful; she protested, even cried, but Ben stayed firm, explaining that she needed help. Once she was admitted to the hospital, the house felt quieter, almost lighter.

Lucas struggled at first. He’d ask about Emily, sometimes wondering if she was coming back. But gradually, he began to understand that what he’d believed wasn’t real, and he started to make peace with the truth.

Through it all, Ben and I grew closer, supporting each other as we helped Lucas cope.

A happy couple | Source: Midjourney

A happy couple | Source: Midjourney

It wasn’t the journey I expected when I married him, but somehow, we’d come out stronger on the other side, bound together not just by love, but by everything we’d faced as a family.

If you loved this story, here’s another one for you: When Ruth entered her in-laws’ house, she sensed something was wrong. The unsettling silence and her father-in-law’s strange text were just the beginning. But when she followed a mysterious noise to the attic and unlocked the door, nothing could have prepared her for what she found.

A shocked woman | Source: Midjourney

A shocked 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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