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 Had Doubts about Dating a Single Dad, but What I Found after He Moved into My House Left Me Pale

I came home expecting a quiet evening, but what I found instead shook me to the core. In that moment, I realized my trust had been betrayed, and my peaceful life was about to be turned upside down.

When I first started dating Ryan, I knew there would be challenges. I was stepping into a relationship with a man who had three young daughters, and I was prepared for the extra noise, the mess, and the constant whirlwind that would follow us wherever we went.

Woman laughing with her husband | Source: Midjourney

Woman laughing with her husband | Source: Midjourney

I had been living alone in my cozy, peaceful home for years and had gotten used to the calm and order that came with it. But I knew that loving Ryan meant embracing the chaos his daughters would bring, and I was ready to make the necessary sacrifices.

My home was my sanctuary, but I was willing to adjust. When Ryan moved in, I sacrificed my guest room and the upstairs rec room so the girls could have their own spaces. It wasn’t always easy.

Middle aged couple standing in their house | Source: Midjourney

Middle aged couple standing in their house | Source: Midjourney

I would often find myself retreating to my bedroom just to get a moment of quiet. But I was committed to making our new family dynamic work, so I kept reminding myself that this was what it meant to love someone—sacrifices, compromises, and the willingness to adapt.

But just when I thought I had a handle on things, the situation took a turn I never saw coming.

Ryan’s ex-wife, Laura, had always been a bit of a wild card. She was the kind of person who thrived on drama and attention. So, when she suddenly decided to get the girls a dog, three kittens, and a bunch of rodents, I wasn’t entirely surprised.

A woman with her cats | Source: Midjourney

A woman with her cats | Source: Midjourney

What did surprise me was the fact that her lease strictly prohibited pets. I couldn’t understand why she would make such a reckless decision, knowing it would cause problems. But I chalked it up to her trying to win the girls’ favor, hoping they’d see her as the “fun” parent.

I thought that would be the end of it, that she’d have to face the consequences of her actions on her own. “She’ll sort it out,” I muttered, hoping Ryan would agree. But that wasn’t the case. When her landlord found out about the pets and threatened to evict her, Ryan stepped in, determined to play the hero. “They can stay with us,” he told the girls with a reassuring smile, “We’ll make room.”

Ryan smiles at his daughter | Source: Midjourney

Ryan smiles at his daughter | Source: Midjourney

“Are you serious?” I asked, my voice sharp with disbelief. “We can’t possibly take in all those animals, Ryan. You know I have allergies, we both work long hours, and let’s be honest, you’re not exactly the most reliable when it comes to keeping the house in order.”

He frowned, clearly taken aback. “But they’re just kids,” he pleaded. “They’ve already fallen in love with the animals. How can we take them away now?”

“I get that,” I replied, trying to stay calm. “But maybe a few of the rodents could stay, not the entire zoo. We can’t turn this place into a circus.”

A woman arguing with her husband in their bedroom | Source: Midjourney

A woman arguing with her husband in their bedroom | Source: Midjourney

The girls, overhearing our conversation, looked devastated. They had already become attached to the animals, and now they were faced with the possibility of losing them.

Ryan, caught in the middle, started sulking, his usual response when things didn’t go his way. Meanwhile, his ex, ever the drama queen, played the victim. She acted as if I was the evil stepmother ruining everyone’s fun, and that’s how the girls started to see me too.

Sad man sulking in his bed | Source: Midjourney

Sad man sulking in his bed | Source: Midjourney

Then, one afternoon, after a particularly exhausting day at work, I came home ready to unwind. As I pushed open the door, I froze. My living room looked like an animal shelter.

The dog was lounging on my couch, the kittens were scampering around like they owned the place, and the rodents were making themselves at home in the corners. My throat started itching almost immediately, my nose tingling with the telltale signs of an impending allergy attack.

A dog on the couch | Source: Pexels

A dog on the couch | Source: Pexels

I felt a surge of anger, betrayal burning in my chest. Ryan had brought all the animals over behind my back. As I stood there, trying to process what was happening, one of the girls, Emma, approached me, looking guilty.

She hesitated before blurting out, “Mom told us you wouldn’t mind the pets because you told her you liked animals. But when we were at dinner last week, I heard you tell Dad that you had allergies. I think Mom heard too.”

Girl whispering something to her mother | Source: Midjourney

Girl whispering something to her mother | Source: Midjourney

I didn’t react right away, just nodded and reassured her that it wasn’t her fault. But that was the first crack in the story I’d been told. Why was Ryan’s ex lying to her kids?

That’s when it clicked. Ryan’s ex had done this on purpose. She’d overheard me talking about my allergies and decided to use it against me, knowing it would cause chaos in our home. I was furious, but I also realized that I wasn’t going to let her get away with it.

A woman has a moment of realization | Source: Midjourney

A woman has a moment of realization | Source: Midjourney

That evening, I confronted Ryan. “Why did you bring the animals here without telling me?” I asked, my voice trembling with barely controlled anger.

He looked at me, guilt written all over his face. “I didn’t think it would be a big deal. The girls were so upset, and I just wanted to make them happy.”

“And what about me?” I shot back. “You know I have allergies. You know how hard it is for me to keep up with the housework as it is. Why didn’t you talk to me first?”

Woman arguing with her husband | Source: Midjourney

Woman arguing with her husband | Source: Midjourney

Ryan sighed, running a hand through his hair. “I’m sorry. I just… I didn’t want to disappoint them.”

I shook my head, feeling a mixture of anger and sadness. “Ryan, this isn’t just about the animals. It’s about trust. You went behind my back, and you let your ex manipulate you. We’re supposed to be a team, and right now, it feels like I’m fighting this battle alone.”

Frustrated woman looking down | Source: Midjourney

Frustrated woman looking down | Source: Midjourney

He looked at me, his expression softening. “You’re right. I should have talked to you first. I won’t let it happen again.”

But I wasn’t satisfied with just an apology. I needed to get to the bottom of what had really happened. I decided to dig deeper.

The next day, I made a few phone calls. It wasn’t hard to find the truth once I knew where to look. I managed to get in touch with her landlord under the guise of verifying some information about his other property. When I casually mentioned the pet situation, he was puzzled.

Landlord talking on the phone | Source: Midjourney

Landlord talking on the phone | Source: Midjourney

“I’ve never had a problem with pets,” he said. “In fact, I encourage it. Makes the place feel more like home, you know?”

That was all I needed to hear. Ryan’s ex had lied. She’d never been at risk of eviction. She’d used the pet issue as a way to manipulate the situation, knowing it would cause a rift between Ryan and me, and likely hoping I’d cave in to keep the peace.

Middle aged woman talking on the phone | Source: Midjourney

Middle aged woman talking on the phone | Source: Midjourney

That evening, I confronted Ryan again, this time with the full story. “I talked to her landlord,” I said, watching his face carefully. “He doesn’t have any problem with pets. She lied about being at risk of eviction.”

Ryan was floored. He stared at me, disbelief and anger flickering in his eyes. “She lied?” he asked, his voice barely above a whisper.

I nodded. “She used the situation to stir up trouble between us. She knew it would cause problems, and she did it anyway.”

Sad middle-aged man | Source: Midjourney

Sad middle-aged man | Source: Midjourney

Ryan clenched his fists, anger radiating off him in waves. “I can’t believe she would do that. I feel like such an idiot.”

I reached out, placing a hand on his arm. “You’re not an idiot, Ryan. But you need to see her for who she really is. We can’t let her manipulate us like this. We need to be stronger together.”

He looked at me, a mixture of regret and determination in his eyes. “You’re right. I’m sorry I didn’t see it sooner.”

Middle-aged man hugging his wife | Source: Midjourney

Middle-aged man hugging his wife | Source: Midjourney

The next day, I texted Ryan’s ex. I calmly explained that I knew the truth and that the animals needed to go back to her place. When she tried to argue, I reminded her that her own landlord had no issue with pets. She had no choice but to take them back.

The girls were understandably upset when they found out that their mom had lied to them about the pets. It wasn’t easy for them to reconcile that their mom had used them as pawns in her own game. But in the end, it brought some much-needed clarity to the situation.

Girls holding their pets | Source: Midjourney

Girls holding their pets | Source: Midjourney

Ryan and I had a serious talk about trust and communication. I made it clear that if we were going to make this work, we needed to be a team, making decisions together and not letting outside forces pull us apart. He agreed, and while things weren’t perfect, we were on the same page for the first time in a long while.

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.

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