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.

During my grandfather’s funeral, a stranger gave me a note — I couldn’t help but laugh after reading it because Grandpa had played a trick on us

At Grandpa’s funeral, 18-year-old Dahlia feels isolated as her family fumes over the pitiful $1 inheritance. But when a stranger slips her a secret note, Dahlia is pulled into a mystery only she can solve.

I stood by the graveside, hands clenched in the pockets of my too-small black dress, listening to the priest’s droning voice blend with the rustle of the wind.

This was the saddest day of my life, but everyone else in the family seemed more concerned with glaring at each other than mourning Grandpa.

I could feel their bitterness lingering in the chilly October air, thick like syrup. One dollar each. That’s all Grandpa left us in his will, and they were furious. But me? I wasn’t angry. Just… hollow.

Grandpa wasn’t supposed to be gone. He was the only person who ever saw me, not the mess-up or the spare kid nobody paid attention to, but me. He let me in when no one else cared.

I stared down at the flowers resting on his coffin. I’d brought him a red rose, and it stood out among the white daisies everyone else had placed on the casket.

“One dollar,” Aunt Nancy hissed from behind me. “One damn dollar! That man was loaded, and this is what we get?”

Uncle Vic let out a bitter laugh. “Right? I swear he did it on purpose, the spiteful old man.”

“Typical Dad,” Mom muttered, crossing her arms tight across her chest. “He always played favorites, and Dahlia here was his little pet. Bet she got something we don’t know about.”

Aunt Nancy’s eyes cut toward me, sharp as glass. “What did he leave you, Dahlia? Anything? Don’t act like you didn’t get something.”

I stiffened. “I got the same as all of you.”

Mom’s fingers tightened over my shoulder. “Are you sure?” she asked in a low voice. “You were always with him. Maybe he told you something… think hard, Dahlia. You owe it to your family to share whatever he gave you.”

Memories came rushing back of Grandpa’s goofy stories about long-lost treasure and the butterscotch candies he always kept in his coat pocket.

Sometimes, he’d wink at me and say, “One day, kiddo, I’m leaving you a treasure. Real treasure!” But it was just a game, a joke between us.

I shook my head and turned my gaze back to the coffin. “What Grandpa gave me was his love, his stories, and a place that felt more like home than my actual home. Those things were worth more than money, and there’s no way I can—”

“Nobody cares about any of that!” Mom snapped. “Think, girl! What happened to all of his money?”

I shrugged. I truly didn’t know the answer to her question and didn’t care. Grandpa was gone. He was my confidant, my safe place, my friend. I’d lost the most important person in the world, but all they cared about was slapping a price tag on his death.

“She knows something,” Vic muttered, loud enough for me to hear.

Their voices twisted together, accusing, scheming — like they could squeeze secrets out of me if they tried hard enough. But I had no secrets that could earn them more money.

The second they realized there’d be no fortune, they turned away from the grave and stormed off. I could still hear them bickering as they walked away, lashing out at each other like vultures. It made me sick.

“You must be Dahlia.”

I looked up to see a woman, maybe in her 60s, with kind eyes and a worn leather bag slung over her shoulder. Her smile was soft and secretive, like she knew something the rest of us didn’t.

“I was a friend of your grandpa’s,” she said, leaning in as if we were co-conspirators. “He asked me to give you this.”

Before I could respond, she slipped a folded piece of paper into my hand and whispered, “Don’t let anyone see it, especially your family.”

Her presence felt surreal, almost dreamlike, and before I could say anything, she was gone, swallowed by the crowd of mourners. My heart pounded in my chest as I unfolded the note.

111 locker — Southern Railway Station.

For a second, I stood frozen, the words blurring in front of me. Then it hit me: Grandpa’s “treasure.” A laugh bubbled up from my throat, inappropriate and wild, but I couldn’t help it. He wasn’t joking after all.

That night, I lay in bed staring at the ceiling. The note was tucked under my pillow like a secret. Grandpa’s voice echoed in my mind, playful yet certain: “Locker number 111… There’s treasure in there, kiddo!”

A weight settled on my chest, something between grief and hope. What if this wasn’t just some wild goose chase? What if Grandpa had really left something for me, hidden away where no one else could reach?

The thought twisted around in my mind until I couldn’t take it anymore. I needed to know what was in that locker.

I called a cab the next morning. It was the first thing I did after I woke up. As I tiptoed past the kitchen, I could hear Mom muttering on the phone about Grandpa’s will, probably trying to squeeze sympathy or cash out of anyone who would listen.

I clenched my jaw and slipped out the door, the chilly morning air hitting my skin like a slap.

The ride to Southern Railway Station felt like the longest 20 minutes of my life.

My knee bounced with nervous energy as the cab wound through narrow streets, past graffiti-covered walls, and empty coffee shops just starting to open. The driver glanced at me in the rearview mirror but didn’t say a word.

When we finally pulled up at the station, I stepped out and asked him to wait for me. I clutched the note tightly as I entered the train station.

The station smelled like diesel and stale popcorn. People rushed past me in every direction — commuters, travelers, strangers with places to go.

I hesitated at the entrance, suddenly feeling small and out of place. But then Grandpa’s voice floated back into my mind, steady and reassuring: “Real treasure, kiddo.”

I took a deep breath and headed toward the lockers and I could hear my heart pounding. Rows of metal boxes lined the wall, each one looking identical: gray, dented, and slightly rusty.

My eyes scanned the numbers until I found number 111.

I reached into my pocket and pulled out the folded note. The key was taped to the back. With trembling fingers, I peeled it off and slid it into the lock.

For a second, it jammed, and I panicked. But then — click! The lock turned, and the door swung open.

Inside was a duffel bag. It was old, faded, and heavy. My hands shook as I pulled it out and unzipped it.

The bag was full of cash. Bundles upon bundles of it!

I gasped, my mind reeling. It couldn’t be real, could it? I reached in and pulled out a stack, flipping through crisp hundred-dollar bills. There had to be at least $150,000 in there.

And tucked inside the bag was another note, written in Grandpa’s messy scrawl:

For my beloved granddaughter, everything I saved is now yours. Take it and live free, kiddo. The rest of the family may not see your worth, but I’ve always believed in you.

Tears blurred my vision, and I hugged the note to my chest, a knot forming in my throat. This wasn’t just money. It was freedom — a way out.

Grandpa always knew how badly I needed to escape this family. And now, he’d given me exactly what I needed and tricked everyone else in the process!

I zipped the bag shut, slung it over my shoulder, and walked out of the station, my heart pounding in tune with my footsteps.

The early morning sun was just starting to peek through the clouds, casting everything in a soft, golden light. For the first time in years, I felt… light.

During the cab ride back, I stared out the window, watching the city come to life. I had options now. No more suffocating family dinners, no more being ignored or treated like an afterthought, no more being the family scapegoat.

I could leave. I could build something new.

The thought scared me as much as it excited me, but Grandpa’s voice echoed in the back of my mind: “Live free, kiddo.”

As the cab pulled up to my house, I made my decision. I wasn’t staying. Not another minute!

I didn’t even bother going inside. I pulled out my phone, booked a ticket to anywhere, and told the driver to head straight to the airport.

With the duffel bag in my lap and Grandpa’s note tucked safely in my pocket, I smiled for the first time in days.

I was free. And for the first time in my life, I knew exactly what that meant.

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