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 wife started to distance herself from my daughter and me. One day, she left an envelope and disappeared

When my wife started pulling away from me and our daughter, I couldn’t understand why. My heartbreaking story is about how someone can love you so much that they try to protect you by all means. Read on to see how we traversed secrets, innocent lies, and heartache to unite as a family.

There’s something deeply unsettling about not knowing the whole story, especially when it involves the people you love the most. Okay, let me backtrack a bit, my name is Kevin, and Levine and I have been married for 15 lovely years.

We share one amazing child, Emily, who is still quite young and attending school. My wife and daughter mean the world to me, and I believe we have a great family. However, around six months ago, Levine started withdrawing and avoiding me and our daughter.

For months, I watched as my formerly loving and caring wife grew increasingly distant by the day. What started as small changes in her demeanor escalated into full-blown avoidance. Her smiles are fewer and her nights spent awake longer.

I even sometimes caught glimpses of her crying in the bathroom more than once. But every time I approached her about it, she brushed off my concerns with a shaky “I’m fine.” Yet, she wasn’t. And deep down, I knew it.

This unspoken “thing” hung over me and our daughter heavily, causing our family relationships to start cracking.

“Levine, please talk to me,” I pleaded one evening, finding her again at the window, staring into the backyard. Her back was to me, her shoulders tense.

“I just need some air, Kevin. That’s all,” she murmured, her voice hardly above a whisper.

I stepped closer, my concern deepening. “It’s been months of ‘just needing air.’ You’re scaring me, baby. You’re scaring Emily.”

She turned then, her eyes wet with unshed tears. “I can’t, not yet…” her voice trailed off as she turned back to the window, leaving me standing helplessly behind her.

I returned home yesterday from picking Emily up at school to find the house eerily silent. The morning Levine left was like any other, except she didn’t say goodbye. My stay-at-home wife wasn’t anywhere when we arrived.

However, on the kitchen table amidst the usual clutter of mail and Emily’s school books that she had come with, I found THIS DREADFUL ENVELOPE. My name scrawled across it in Levine’s familiar handwriting.

My heart sank to my stomach as I tore it open with trembling hands. Inside, her letter lay, written in the same shaky hand that had addressed the envelope. As I opened it, tears streamed down my face as I found out what she had been going through all along:

“My dearest husband,

If you’re reading this, then I am already gone. I couldn’t bear to tell you in person, for fear I would never be able to leave. I have been diagnosed with stage 3 cancer, and the doctors are not hopeful. It is my deepest fear to become a burden to you and our beautiful Emily.

I want to protect you both from the pain of watching me deteriorate. I love you both more than life itself, and it’s because I love you that I need to do this. Please understand that this is the hardest choice I’ve ever made, but it’s made out of love. I am at Clear Life Center, a quiet hospice two states away. Please forgive me.

With all my love, always,

Levine.”

Tears blurred my vision as I tried to compose myself. My lovely, beautiful wife had chosen solitude over the anguish she believed her illness would cause us. If I thought I loved her before, at that moment I realized I loved her MORE THAN EVER.

Without a second thought, I packed a bag. I told Emily, “My baby, mommy’s not feeling too well, and we are going on a little trip to see her, okay?” My brave little girl with a worried face asked, “Is she going to be okay, Daddy?”

Not wanting to lie to her, I replied, “She’s going to feel much better when she sees us, I promise.” We drove straight to the facility my wife mentioned, desperate to be with her, regardless of her wishes to shield us.

When we arrived and I found her, the reality of her condition hit hard. Levine was frail, a shadow of the vibrant woman I had fallen in love with. Yet, when she saw us, her eyes lit up with a mix of joy and sorrow, and she instantly looked better, than I had envisioned!

“Kevin, Emily,” she murmured, reaching out weakly.

“Mom, why didn’t you tell us? We could have helped…” Emily sobbed, clutching her mother’s hand. “I thought… I thought it would be easier this way,” Levine whispered, tears streaming down her face.

“We needed to be here, with you. No matter what,” I said, gripping her hand.

We spent those last weeks of her illness by her side, achieving her life goals before her death. Whenever she was strong enough, we went out for walks, well, she was in a wheelchair. She got to tell Emily all the things she wished her to know before her passing.

“I’ll always love you, my sweet baby girl. And I want you to know that I will be with you in spirit for all the days of your life,” Levine told Emily as they embraced, shedding more tears.

We talked, laughed, and sometimes sat in silence, savoring the precious moments we had left. Emily read her favorite books aloud, and I held her mother’s hand every night until she fell asleep.

My darling wife passed away holding my hand. Emily curled up beside her, a peaceful expression on her face. Her last days were not filled with the pain and suffering she had feared but with love and the warmth of her family.

In the wake of her passing, I’ve come to realize the profound strength it took for her to make the decision she did. Levine’s act, initially so incomprehensible to me, was one of selfless love. The kind that sees beyond immediate pain to the eventual peace it can bring to those left behind.

Now, as Emily and I adjust to a world without Levine, we do so with a deep understanding of her last gift to us. Not just the envelope that explained her absence, but the enduring presence of her love.

A love that, like the subtle fragrance of her favorite flowers, lingers around us, invisible yet palpable. It remained a gentle reminder that even in their absence, love remains.

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