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.

Bride Claimed I Destroyed My Son’s Wedding Because of My Outfit Choice – Was I Really Wrong Here?

Claire just wants to be the glamorous mother-of-the-groom—but when she realizes that her daughter-in-law has her own plans for the wedding, she steps back to focus on her own outfit, only for there to be a fight between her and Alice on the big day. Alice claims that Claire has destroyed the wedding by stealing her dream dress, while Claire sees nothing wrong in her actions. Who is wrong?

All I wanted was to be the mother-of-the-groom. That’s it. I just wanted to be the doting mother who loved her son more than anything—but this is the story of how my attempt to make my son’s wedding perfect turned into a day we’d all rather forget.

When Mark introduced Alice to us, she was unlike anyone I expected him to fall for. Mark, my son, is a lawyer at a top firm—a position that he secured straight after his graduation from Stanford.

“I’m going to be a lawyer, Mom,” he told me once when he was still in high school and doing an essay on the career he wanted to get into.

“I could easily see that,” I told him, making him breakfast as he worked away.

“It’s to help fight injustices. For children, specifically,” he said, drinking his orange juice.

Mark had big dreams, and I knew that my son was always going to reach for the stars.

Alice, on the other hand, was completely different from my son. Her entire personality was light and carefree, whereas Mark was serious and brooding. Alice was a self-taught coder, who freelanced from their cozy apartment. Their worlds, their politics, their interests didn’t align.

But they made it work—and they were a sweet couple for the most part. But love, as they say, is blind.

When Mark proposed to Alice, we were all invited to the scene to help surprise her.

“Please, Mom,” Mark said on the phone. “Alice isn’t close to her family, so to see you and Dad there will be good for her. She’ll know that she’s welcomed and supported.”

“Of course, honey,” I told him, already envisioning their wedding in my head.

I swallowed my reservations and offered to pay for the wedding. James and I had put money away for Mark’s studies, but he had always gotten bursaries which paid for it all.

“We can just use that money for the wedding, Claire,” my husband said over lunch the day after the proposal.

“It’s the best thing we could do for them,” I agreed. “This way they can save up to move out of that small apartment. I know Mark’s been talking about a house with a garden because he really wants a dog.”

When we told Mark and Alice, I thought that the gesture would bring us closer. I didn’t have any daughters, so I thought that this would be my chance.

I could get to know Alice better—and that would be good for Mark, to know that his wife and his mother got along well. Instead, the wedding planning only highlighted our differences.

After a few months into the wedding planning, I met Alice at a coffee shop so that we could go over the details. But we clashed on everything.

“I think roses are timeless,” I said, helping myself to a slice of cake.

“They are, but they’re also overdone in a sense,” Alice said, sipping her tea. “Mark and I want peonies.”

Our meeting went back and forth a few times—and we were stuck in a space where we just couldn’t agree on anything.

“Okay, how about this?” I asked her. “You go ahead with everything else, and just tell me what color your bridesmaids are wearing, so that there won’t be any clashes.”

“They won’t be wearing green,” she said. “I’m leaning toward pink.”

I paid the bill and we parted ways with the wedding planning.

But then, one afternoon Alice texted me.

Hi Claire, just picking out my wedding dress with the girls! I’m so excited! I wish you were here!

Attached were photos of her five top wedding dress picks.

I knew that Alice and I were on different ends of what we thought that the wedding should look like, but I wanted to be included in the big things. I wished that she had included me in the wedding dress shopping.

“At least she’s sending you the top picks,” James said as he read the newspaper next to me.

“I know, but it’s not the same,” I said.

“Do they look good?” he asked. “Can I see them?”

Together, we scrolled through the photos of the potential dresses. They were adequate choices, but nothing stood out.

Nothing that would fit the standard of my future daughter-in-law.

The dress that was Alice’s favorite and the first contender for the actual wedding dress wasn’t what I expected.

I typed back, telling Alice that it wasn’t quite the best choice. And I hoped that my financial stake in the wedding would weigh in. James and I hadn’t given the kids a budget. They had everything at their disposal.

Why not consider the second one? It might be more flattering for you.

James chuckled beside me.

“You’re at the point of over-stepping,” he said.

Before I could say anything, my phone pinged with a message from Alice.

Sorry, but I disagree. This is the dress I’m choosing.

That night over dinner, as James was plating our salmon, I shared my frustration with him.

“Alice is not even considering my opinion, and I’m paying for the dress!” I exclaimed.

James tried to mediate; he also texted Mark to make sure that he knew how I felt, too.

“I think you should just leave the wedding planning to them now,” James said. “Put all your attention into yourself and what you’re going to wear.”

But it also turned out that Mark was able to persuade Alice to wear the dress I preferred.

I had to admit, it was the less stressful option, and I hadn’t been able to shop for my dress before that.

So, that’s what I did.

I went to a few different boutiques and eventually found my perfect dress. It was emerald green, which I knew brought out my eyes.

“That’s beautiful,” James said when I tried the dress on for him.

I had felt different. I no longer felt like the mother-of-the-groom who had been pushed aside. Instead, I felt beautiful in my own skin, my self-esteem growing every time I thought of the dress.

When the wedding week loomed upon us, James and I tried to make ourselves as present as possible. We went to all the events that Mark and Alice needed us to be at—including the rehearsal dinner where we saluted them and drank champagne to toast the festivities.

“All sorted, Mom?” Mark asked me. “Your dress and everything?”

I smiled at my son. Despite being in the middle of Alice and me, he was always checking in on me.

“Of course,” I said. “I’m ready to celebrate you and Alice.”

On the morning of the wedding, I put on my green dress and did my make up. It was everything I had wanted to look for my son’s wedding—elegant and sophisticated.

As I arrived at the venue, the air was thick with murmurs. I ignored them, thinking that everyone was just so used to me being dressed in comfortable clothing, that this was something different for them.

I went straight to the bride’s dressing room, hoping to see Alice and compliment her before she walked down the aisle.

Upon opening the door, Alice looked up—her joyful expression collapsing into one of utter devastation. She looked me up and down before bursting into tears.

“Why did you do this to me, Claire?” she sobbed, her voice choked with emotion.

Confused, I stepped into the room and closed the door.

“What’s wrong?” I asked her.

“Your dress!” she exclaimed.

“What about it?” I asked, second-guessing everything.

“It’s my dream wedding dress, just in another color,” she said, nearly shouting.

I was taken aback.

“Alice, honestly,” I said. “I didn’t realize—they look so different in color.”

But Alice wasn’t having any of it. She sat on the edge of the couch, her head in her hands.

“How could you?” she looked up and cried out. “You’ve made this day about you! Just because we didn’t take any of your suggestions!”

Mark, having heard the commotion from his dressing room next door, came rushing in.

“Mom? What’s going on here?” he asked me.

He looked from Alice to me, seeking an explanation.

Trying to calm the waters, I explained everything slowly.

“I didn’t see the resemblance, Mark,” I said. “I truly just loved the dress, and I thought—”

Alice stood up and marched toward Mark.

“No!” she exclaimed. “You thought that you’d show me what I could’ve had, but in green. Isn’t that it?”

“Mom, please,” my son said. “Let’s just try to get through the day. Please, for me.”

I agreed and left the dressing room. I just wanted to find James and sit quietly until the day was over.

I knew that Alice and I were walking a thin line, but I didn’t expect her to shout at me in the manner that she did.

Naturally, I was upset, but I didn’t want to ruin their day any further.

Reflecting now, perhaps I should have been more open to Alice’s preferences. It was her day after all, not just mine to orchestrate. The question of whether I was wrong hangs heavily over me.

Yes, in trying to enforce my vision, I might have lost sight of what was truly important—Alice’s happiness and Mark’s peace on their special day.

Was I wrong for what I did?

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