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 Returned Home from My Daughter’s Funeral to Find a Tent in My Backyard — I Went Pale at What I Found Inside

After burying her eight-year-old daughter, Lily, Ashley returns home, drowning in grief and exhaustion. But something unexpected awaits in her backyard, pulling her out of the numbness and forcing her to confront a mystery she never could have anticipated.

I wasn’t ready to say goodbye, even though I thought I was. They said it would be peaceful at the end, and maybe it was for Lily. But for me, the pain cut deeper than anything I could imagine. My little girl was gone, and I didn’t know how to make sense of a world without her in it.

A grieving woman | Source: Pexels

A grieving woman | Source: Pexels

It’s been a week since we laid her to rest. The days leading up to her death were a blur of hospital beds, whispered prayers, and the slow, cruel slipping away of her laughter. Today, we buried her, but it didn’t feel real. I moved through the funeral like a shadow of myself. Family and friends came, faces blurred by my tears.

“Ashley, I’m so sorry,” Aunt Ruth said, wrapping me in her arms. Her perfume was too strong. I didn’t want to be hugged. I just wanted Lily.

Two grieving women hugging | Source: Pexels

Two grieving women hugging | Source: Pexels

“She was such a light,” someone else added. I nodded, but I couldn’t really hear them.

All I could think of was Lily’s laugh. How her little giggle could fill a room. I’d never hear it again. That thought crushed me more than anything. I wanted to scream, but no sound came out.

A silent woman looking at a headstone | Source: Pexels

A silent woman looking at a headstone | Source: Pexels

As people filtered out, offering their condolences, I just kept staring at the empty chair where Lily should’ve been. My body felt heavy, like I was dragging myself through mud, and my mind kept wandering back to her final days.

“Let me know if you need anything,” a voice said as I walked out of the cemetery. I nodded but didn’t respond. What could anyone do?

A crying, grieving woman | Source: Pexels

A crying, grieving woman | Source: Pexels

The drive home was silent. I couldn’t turn on the radio—music felt wrong, somehow. I just wanted quiet. The kind of quiet where you can pretend the world stopped with your grief.

When I pulled into the driveway, I wasn’t even sure how I got there. I sat in the car for a minute, staring at the house, trying to gather the energy to go inside. I didn’t want to face that empty space. Not without her.

But something stopped me before I could get out.

A woman driving at night | Source: Pexels

A woman driving at night | Source: Pexels

There, in the backyard, was a tent.

A huge, brightly colored tent. The kind you’d see at a circus. Red and yellow stripes, with little flags fluttering at the top. It didn’t make sense. My heart jumped into my throat.

“What… is that?” I whispered to myself.

A bright tent | Source: Pexels

A bright tent | Source: Pexels

I blinked, rubbed my eyes. Maybe I was hallucinating. Grief does strange things to people, right? I was exhausted and emotionally drained. But no, the tent was still there. Bold, bright, and out of place. It was like a splash of color in a black-and-white world.

I got out of the car slowly, my legs feeling like they might give way at any second. Who would put a tent in my yard? And on today, of all days? My head spun with questions. Was this some sort of prank? Or had I completely lost it?

A shocked woman | Source: Freepik

A shocked woman | Source: Freepik

I walked closer, every step feeling heavier than the last. The wind picked up, rustling the colorful flags on top of the tent. My heart pounded so hard I thought it might burst.

“This can’t be real,” I muttered, clenching my fists.

A sad, thoughtful woman | Source: Pexels

A sad, thoughtful woman | Source: Pexels

But it was real. As I got closer, I could see the details—the stitching on the fabric, the wooden stakes holding it in place. My mind raced. There was no note, no sign of who had put it there or why.

I reached out, my hand trembling as I touched the flap of the tent. It felt solid, real. My stomach twisted. I didn’t want to open it, but I had to know what was inside.

A huge lit up tent | Source: Unsplash

A huge lit up tent | Source: Unsplash

With a deep breath, I gripped the edge of the flap and pulled it open.

I opened it slowly, my breath shallow, heart racing. Inside, there was something bundled up in the middle of the space. For a second, my mind couldn’t make sense of it. It was wrapped in a blanket, small and still. My stomach twisted, and I couldn’t stop the flood of memories that hit me all at once.

A small blanket with something inside | Source: Midjourney

A small blanket with something inside | Source: Midjourney

Lily, lying in the hospital bed. So pale. So fragile. The tubes, the machines. I remember her tiny body swallowed by the blankets, the way she barely moved in those last few days. My knees nearly buckled under the weight of it all.

“No,” I whispered, my voice trembling. “No, not again…”

I took a step forward, my whole body shaking. The sight in front of me felt like another cruel joke, like the world was mocking me. Why today? Why now?

A scared woman | Source: Pexels

A scared woman | Source: Pexels

Suddenly, the bundle moved.

I gasped, freezing in place. My heart pounded so loud I could hear it in my ears. For a split second, I didn’t know what to do. My mind spun, expecting the worst, preparing for more pain.

A blanket in a tent | Source: Midjourney

A blanket in a tent | Source: Midjourney

But then, a small head popped out from under the blanket. A tiny Labrador puppy, its fur soft and golden like sunlight. It blinked up at me with wide, curious eyes, a pink bow tied around its neck. My breath caught in my throat. I stared, completely overwhelmed.

“What… what are you doing here?” I whispered, my voice cracking.

A small Labrador puppy | Source: Unsplash

A small Labrador puppy | Source: Unsplash

The puppy wiggled out of the blanket and stumbled toward me, wagging its little tail. It was so full of life, so innocent, a stark contrast to the grief that had consumed me for so long. I knelt down slowly, reaching out to touch the soft fur, still in disbelief. My fingers trembled as they brushed against the puppy’s coat, warm and alive.

Tears welled up in my eyes. “Why is there a puppy here? Who did this?” My voice broke, the confusion mixing with the heavy sadness I had carried all day.

A sad tearful woman | Source:Freepik

A sad tearful woman | Source:Freepik

As I stroked the puppy, I noticed something else—an envelope tucked under the blanket. My heart skipped a beat. With shaking hands, I picked it up and stared at it for a moment. The handwriting on the front was familiar. My breath hitched as I recognized it. Lily’s handwriting. Messy, but hers.

Tears blurred my vision as I carefully opened the envelope. Inside was a note, short and simple. My hands shook as I read the words.

An envelope with a note | Source: Pexels

An envelope with a note | Source: Pexels

“Dear Mommy,

I know you’re sad because I had to go to heaven. But I wanted to leave you something to help you smile again. I asked Daddy to get you a puppy, so you’ll have someone to cuddle with when you’re missing me. Her name is Daisy, and she loves to play! Please take care of her for me. I’ll always be with you, watching from above. I love you so much.

Love, Lily.”

A child writing a letter | Source: Pexels

A child writing a letter | Source: Pexels

I dropped to my knees, clutching the note to my chest. The tears came in waves, and I couldn’t stop them. I cried harder than I had at the funeral. Harder than I had since the moment I knew I was losing her.

“Lily…” I sobbed, my voice barely a whisper.

A close-up shot of a crying woman | Source: Pexels

A close-up shot of a crying woman | Source: Pexels

Even in her final days, my sweet little girl had been thinking of me. She knew. She knew how much I’d miss her, how much it would hurt. And she found a way to make sure I wouldn’t be alone. A puppy. A new life to care for, to love.

I held Daisy close, the warmth of her little body grounding me in the moment. I could still feel Lily’s presence. The tent, the puppy—it was all part of her last gift to me. A way to remind me that even though she was gone, her love would always be with me.

A labrador puppy looking up | Source: Freepik

A labrador puppy looking up | Source: Freepik

The tent didn’t feel so strange anymore. It was a place for me to find Daisy, a place to feel connected to Lily one more time.

Over the next few days, Daisy became my shadow. She followed me everywhere, her tiny paws tapping on the floor as she scampered after me. At first, I didn’t know what to do. How could I care for this puppy when my heart was so shattered?

A sad woman hugging herself | Source: Pexels

A sad woman hugging herself | Source: Pexels

But Daisy didn’t give me much choice. She’d nuzzle into my side when I was curled up on the couch, licking my hand until I smiled through my tears. She’d bounce around with her little pink bow, full of energy and joy, reminding me of the brightness Lily used to bring.

Every morning, I’d sit with my coffee, Daisy at my feet, and I’d think of Lily. I’d imagine her watching over me, her smile still lighting up the sky. And every time Daisy curled up in my lap, I felt a piece of Lily’s love wrapping around me.

a woman with her dog | Source: Pexels

a woman with her dog | Source: Pexels

Daisy wasn’t a replacement. Nothing could ever replace my Lily. But she was a part of her. A living, breathing reminder of the love Lily left behind. Slowly, day by day, the weight on my chest lightened, just a little.

Taking care of Daisy pulled me out of the fog I’d been in. I had to get up, feed her, play with her. She needed me, just like Lily had known I’d need her.

A smiling woman with her dog | Source: Pexels

A smiling woman with her dog | Source: Pexels

Lily had given me one final gift: a reason to keep going. And even though the pain of losing her would never fully go away, I knew now that I wasn’t facing it alone.

Liked this story? Consider checking out this one: A splitting headache sent me home early, and I hoped for a quiet afternoon alone. But seeing my daughter, who should’ve been at school, and her stepdad behind that closed door shook me to my core. What I discovered tore my heart in two and left me in tears.

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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