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 Sister Showed Up After 15 Years of Silence, Begging for Help, but Her Visit Shattered My Family — Story of the Day

Fifteen years of marriage felt unshakable—until the night my estranged sister, Megan, showed up at my door with nothing but a suitcase and a storm of secrets. What began as an unexpected reunion unraveled into betrayal, lies, and truths I never imagined. Because of that night, my world changed forever.

My husband, Michael, and I sat together in the kitchen, the soft glow of candlelight creating a romantic atmosphere. We were celebrating our 15th wedding anniversary, and I felt special wearing the exquisite earrings Michael had given me earlier.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Their delicate sparkle caught my eye as I glanced at their reflection in my wine glass.

Everything about the moment felt warm and perfect, a quiet escape from life’s usual worries.

Michael lifted his glass with a smile. “Here’s to us,” he said, his voice warm. “To fifteen years of marriage, to love, and to sticking together through all the challenges.”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

We clinked glasses, but my chest tightened. I understood what he meant by challenges.

He was thinking of the heartbreak we had endured, the years of trying for a child, only to discover Michael was infertile.

A sudden knock broke the silence. I frowned. “Who would show up at this hour?” I asked.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Michael sighed. “If it’s Tom, tell him I’m not here.” I knew why—he still hadn’t returned Tom’s hammer.

I laughed, shaking my head, and went to answer the door. But as I opened it, my breath caught.

My heart seemed to stop. Standing there was someone I hadn’t seen in fifteen years.

“Megan…” I whispered, staring at her in disbelief.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“Hi, sis,” she replied softly, her face pale and tired.

“What… what are you doing here?” I managed to ask, stepping aside to let her in. She dragged a small suitcase behind her, the wheels scraping against the floor.

“I… I left Henry,” she said, her voice trembling. Her eyes filled with tears as she struggled to speak. “I didn’t know where else to go. I have no one left. But if you don’t want me here, I’ll understand.”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Before she could say more, I pulled her into a hug. I hadn’t seen my younger sister in 15 years.

The years, the distance, the reason for her leaving—all of it faded as I held her tightly. She hugged me back, her body shaking as she sobbed into my shoulder.

“Where’s your son?” I asked after a moment, stepping back to look at her. Megan had moved to another state when she got pregnant, and I hadn’t heard from her since.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“She’s a girl. Rose,” Megan said, wiping her eyes. “She’s at a camp right now. I didn’t want to involve her in all this yet.”

I nodded, unsure what to say.

Just then, Michael’s voice called from the kitchen. “Did you tell Tom I wasn’t here, and he stormed off in a huff?” He walked into the room, holding his glass. When his eyes landed on Megan, he froze.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“Hi, Michael,” Megan said, her voice sharp and cold.

Michael’s face tightened. “Hello,” he muttered before turning and walking out of the room without another word.

“Don’t mind him,” I said quickly, trying to ease the tension. “You know how he is.”

“Unfortunately, I do,” Megan replied, her tone colder than before.

Megan and I sat at the kitchen table while I prepared us some tea. The quiet clinking of the cups felt heavy, like the calm before a storm.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Once we sat down, I looked at her and asked softly, “What happened with Henry?”

She sighed, her shoulders slumping as if the weight of her story had been crushing her. “It was awful from the start—well, not right away,” she said. “After Rose was born, things seemed okay for a little while. I thought we could make it work.”

Her face tightened. “But then Henry changed. He became cruel, distant. He wouldn’t help with Rose. I spent everything I had on her because he wouldn’t give me a dime.”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

I frowned. “You mean he refused to support his own child?”

Megan nodded. “When I demanded support, he made everything worse. He yelled, threatened… it was unbearable.” Her hands trembled as she spoke, and I felt my chest tighten.

Megan avoided giving too many details about Henry, but her broken tone and tired eyes told me enough.

“Why didn’t you call me?” I asked, my voice trembling. “Why go through all of that alone? I would’ve been there for you.”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

She looked away, her hands gripping the edge of the table. “Helen, stop. We both know why. After what I did… you wouldn’t have forgiven me. Not that easily.”

I shook my head, frustrated and hurt. “You’re my sister. I would’ve helped you, no matter what. But you blocked my number. You didn’t even tell me how to find you. You cut me off completely.”

“I was young,” she said, her voice breaking. “I was stupid and guilty. I thought you hated me.”

I sighed and pulled her into a hug. “I never hated you,” I whispered.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

After a while, I sent Megan to the guest room to rest. I made my way to the bedroom, where Michael lay on the bed with his back to the door. I recognized this posture. He only did that when he was upset.

“Why are you sulking?” I asked.

“You know why,” he muttered without turning to face me.

“Is it because of Megan?” I pressed.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Michael sat up suddenly, his face tight with anger. “Do you not remember how she left, Helen? She stole from you! She took your things, blocked your number, and vanished!”

“I know,” I said quietly. “But it’s been so many years.”

“She took your wedding ring!” he snapped. “And other jewelry. How can you forget that?”

“Maybe she’s changed,” I said.

“People don’t change,” he said, lying back down and turning away from me again. His voice was flat, final, as if no other possibility could exist.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Megan stayed with us for a few days. Each day, Michael’s irritation seemed to grow.

He avoided Megan completely, barely looking at her or speaking a single word. Then, one morning, I went to grab my earrings—the ones Michael gave me for our anniversary—and they were gone.

My heart sank as I searched the jewelry box again, hoping I had overlooked them, but they weren’t there.

“Michael, have you seen my earrings?” I asked, already feeling uneasy.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“No,” he said, his voice sharp, “but I have a pretty good idea where they are.”

“Stop it. She wouldn’t do something like that,” I said, trying to defend Megan.

“Fool me once…” he muttered, letting the unfinished sentence hang in the air.

“I’ll talk to her,” I said firmly. I headed toward the guest room, hearing Michael’s footsteps close behind me.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

I knocked softly and waited until Megan called out, “Come in.” Pushing the door open, I stepped inside. “Have you seen my earrings?” I asked.

“I don’t even know what they look like,” Megan said.

“Then you won’t mind if I check around?” I asked.

“Go ahead,” Megan said, but then added, her tone sharp, “Wait. Do you think I took them?”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“I’m just trying to find them,” I replied, feeling a knot of guilt in my chest.

“Where else would they be?” Michael said from the doorway. “It’s not the first time you’ve stolen.”

Megan’s head snapped toward him, her eyes flashing with anger.

I carefully searched through Megan’s things, feeling both tense and guilty. When I found nothing, I let out a quiet breath of relief.

Then my eyes landed on a book with a thick bookmark sticking out. Something about it caught my attention. I opened it, and there they were—my earrings.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“Megan…” I said, holding them up.

Her face twisted with shock. “I swear, I don’t know how they got there!” she said.

Michael stood behind me, his expression smug. “Maybe you didn’t take anything last time, either?”

Megan’s eyes burned with fury. Her hands balled into fists as she turned toward him. “Enough! I’ve kept quiet for 15 years, but I’m done. I’m telling her the truth!”

Michael’s face changed. For the first time, he looked truly afraid.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“What are you talking about?” I asked.

“Do you know who Rose’s real father is?” Megan spat. “Michael!”

“What?” I said, my voice rising. “That’s impossible. Michael can’t have children. Why are you lying?”

“He can,” Megan said sharply. “He just didn’t want to. That’s why he got rid of me when I told him I was pregnant.”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“Megan, stop,” I said. “Just admit you took the earrings. There’s no need for this.”

“I’m not lying!” Megan shouted. “We slept together. Once. We were drunk. When I told him I was pregnant, he wanted me to get rid of the baby. When I refused, he gave me your jewelry and told me to disappear.”

Tears filled my eyes as I turned to Michael. “Michael? Is any of this true? Do you have anything to say?” I asked.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

He stayed silent, his head bowed.

Megan’s voice broke as she continued. “He pushed me to be with Henry. He wanted me gone. I’ve suffered for all these years because of him!”

Tears streamed down my face. I couldn’t believe the man I had trusted for so many years, my husband, had done something so cruel.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“We got married right after Megan left,” I said, my voice breaking. “How could you lie to me for so long? How could you keep this from me?”

Michael’s face twisted, and his voice shook. “And you believe her? After everything? You’re taking her word over mine?”

“I believed you for too long,” I said, anger rising in my chest. “You made me think you were infertile. You knew how much I wanted children, and you married me anyway. You lied to me about everything!”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“He got a vasectomy right after he found out I was pregnant,” Megan added quietly, her words hitting me like another blow.

Michael opened his mouth, trying to speak, but I cut him off. “Leave,” I said, my voice firm.

“But—” he began, his tone desperate.

“Get. Out,” I said again, my voice shaking but steady.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

He stared at me for a long moment, then sighed and walked out. The slam of the front door echoed through the house.

I collapsed to the floor, sobbing uncontrollably. Megan knelt beside me and wrapped her arms around me, holding me tightly.

“I’m sorry,” I said between sobs. “I’m so sorry I wasn’t there for you as an older sister. I should have protected you.”

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

“And I’m sorry for staying silent,” Megan replied softly.

I wiped my tears and looked at her. “We’ll bring Rose here. You’ll stay with me. We’ll figure it out together.”

Megan nodded, and we stayed there, holding each other. But I felt relief. The truth was finally out.

For illustration purposes only. | Source: Midjourney

For illustration purposes only. | Source: Midjourney

Tell us what you think about this story and share it with your friends. It might inspire them and brighten their day.

If you enjoyed this story, read this one: Caught in a snowstorm, Elina and her mother-in-law, Laura, find themselves on a journey fraught with tension and unresolved grievances. But, as the storm grows more dangerous, an unexpected event forces them to confront their differences in a way that will change their relationship forever. Read the full story here.

This piece is inspired by stories from the everyday lives of our readers and written by a professional writer. Any resemblance to actual names or locations is purely coincidental. All images are for illustration purposes only. Share your story with us; maybe it will change someone’s life.

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