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 Walked up to My Groom at the Altar – All of a Sudden, a Woman in White Dress Appeared behind His Back

After six months of dating, Chris proposes to Beth. His enthusiastic family runs with the wedding planning — only to include unorthodox items on the program, causing Beth to leave her wedding.

For my 25th birthday this year, my boyfriend, Chris, whisked me off to Hawaii.

It was a fairytale because we had only been dating for six months, and I wasn’t expecting anything. But then, Chris proposed to me on the beach — I said yes, swept away by the enchantment of the moment, although I knew that six months of knowing someone was not enough before marrying them.

Little did I know that fairytale was about to unravel into more drama than I had signed up for.

Beach proposal | Source: Pexels

Beach proposal | Source: Pexels

I wasn’t one of those girls who spent hours dreaming up their wedding. So when Chris’s family, fueled by their eagerness and involvement, took complete control over every detail of the wedding, even offering to foot the bill — I allowed it.

I’ll admit that there were moments when I felt sidelined, especially when I said that shades of blue for the color scheme weren’t my cup of tea.

But contributing to their enthusiasm was the better option than fighting with them.

Then, the big day arrived, and I was completely calm about everything — knowing that Chris’s Mom and sister had sorted everything out. I wasn’t close to my family, so other than my father, they didn’t play any big roles.

Blue wedding decor | Source: Pexels

Blue wedding decor | Source: Pexels

“Beth,” his Mom, Leeanne, said, fixing my hair. “I want you to walk down the aisle with your eyes closed.”

“What? Why?” I exclaimed, already thinking about tripping over something while walking.

“I can barely walk properly in these heels with my eyes open,” I chuckled.

“It’s just tradition,” Leeanne said. “I did it, too. The whole thing is about seeing your husband first — the first thing out of the darkness.”

“He’s supposed to be the light,” Chris’s sister, Maggie, giggled.

The whole thing sounded strange. It wasn’t anything I had heard of before, but I also knew that people always came up with superstitions and stories.

“I wouldn’t have to wear a blindfold and mess up my make-up, right?” I asked.

“No, just close your eyes and hold onto your father’s hand tightly,” Leeanne said.

When I told my Dad what I needed to do, he laughed, thinking I was joking.

Pair of glittery Jimmy Choo heels | Source: Unsplash

Pair of glittery Jimmy Choo heels | Source: Unsplash

It was absurd, of course. But my wedding only got worse from there.

At the altar, I opened my eyes, expecting the loving gaze of my fiancé, but I got way more than I bargained for.

Chris smiled at me, and after a second, another sight sent shockwaves through me — a woman in a white dress stood behind him.

I couldn’t tell whether he knew she was there from his expression. I wondered who she was, but the murmurs around me revealed her identity — Julia, Chris’s first wife.

“Chris, what’s happening?” I whispered, pointing to Julia. My voice was barely audible amidst the collective gasps.

Woman standing in white dress | Source: Pexels

Woman standing in white dress | Source: Pexels

But before either Chris or I could process this bizarre twist in the ceremony, Leeanne walked down the aisle, holding onto a little boy’s hand. Every face turned to look toward them.

Then, Julia stepped forward and held her arms open for the boy, ready for him to walk in.

“This is Eli,” she said, looking at me. “He’s six years old, and he is autistic. He’s the best part of me, but he’s also part of Chris. Elizabeth, this is our son.”

“But he wouldn’t tell you that,” Maggie chimed in from next to me — she was one of my bridesmaids.

“Did you know about Eli?” Maggie asked.

Boy covering his face | Source: Pexels

Boy covering his face | Source: Pexels

I shook my head. The air had become dense with emotion. The crowd’s eyes were on me, but my gaze was fixed on Chris, desperate for an explanation, an excuse, a denial, anything.

But there was none. Instead, he fingered his watch nervously, guilt undeniable on his face.

“Why didn’t you tell me?” I demanded, my voice shaking.

“I didn’t know how,” he stammered, avoiding eye contact.

I turned to look at Eli, who was holding tightly onto Julia’s hand and looking around the room. I could clearly see Chris’s features all over his face.

“You let me believe that your divorce was admirable and that there were no ties to Julia,” I said. “But you abandoned your family. You abandoned your son.”

“He abandoned Eli when he found out that he was autistic,” Maggie said loudly.

My heart sank. How could I have almost married a man who was so thoughtless and cold? He left his son behind because of something that he was born with.

As the truth unfolded, I felt I was drowning in the weight of everything. Leeanne, upon discovering that Chris wanted to remarry, had orchestrated this dramatic revelation.

Man holding his tie | Source: Pexels

Man holding his tie | Source: Pexels

“You’re too young, Elizabeth,” she said. “You’re too young to be caught up in his mess. He couldn’t care for Julia, so she cared for herself and Eli. Chris has disappointed me in many ways, but nothing will make up for the neglect of his own child.”

It turned out that my wedding was just a harsh, public lesson aimed at a man who had turned his back on his responsibilities.

I kicked off my heels, handed them to Maggie, and walked away from the altar — not as a bride but as a woman who had narrowly escaped a life bound to deceit.

The experience was painful — sure, it had only been six months of knowing Chris, but I knew what I had felt for him was real. That’s why it hurt so much when I found out the truth.

People holding passports | Source: Pexels

People holding passports | Source: Pexels

In the aftermath, I took time to focus on myself. I decided I needed to travel and live life while still young. I needed more bad romances and horrible dates before figuring out who I wanted to be with.

I just knew one thing for sure — I didn’t want to be with someone like Chris. A man who lied about having a son — a son that was rendered invisible to him because he was autistic.

I’m just grateful that the only thing I had to pay for was my wedding dress — which had been returned three days after the so-called wedding.

Even now, when I think about the entire episode, I admit I’m not mad about it all. Leeanne did what she needed to do. And she did it to protect me and that sweet little boy.

Little boy with red hair | Source: Pexels

Little boy with red hair | Source: Pexels

Has anything unreal happened to you?

Here’s another story for you | Fred is about to get married to Julia when five other women dressed as brides show up and spoil his plans. Julia loves him, and Fred is very convincing. Even after the can of worms is forcefully opened, Julia can’t help but wonder if he is a changed man.

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