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.

Prince Louis and his siblings are ‘likely asking questions’ about Prince Harry

Is it just me or are Prince George, Princess Charlotte, and Prince Louis growing up fast? George, of course, will become king one day, while Charlotte and Louis’ royal lives will likely entail a lot of exciting things. For now, naturally, the most important thing is that they get to remain kids, and Prince William and Kate Middleton appear to be very aware of that.

At the same time, as the three royal children are quietly getting older behind the walls of their royal abode, across the Atlantic in the US their cousins are doing the same thing behind the walls of a multimillion-dollar mansion. Prince Archie and Princess Lilibet live far from the British press, but their parents, Prince Harry and Meghan Markle, have ensured that their children remain hot topics of conversation through their various actions.

Sadly, it’s been reported that Prince George, Princess Charlotte, and Prince Louis have lost contact with their uncle Harry, with whom George and Charlotte had formed a strong bond before he left the Royal Family for good.

That’s something that might soon return to haunt Prince William and Kate Middleton, with a royal expert now painting a sad verdict on what could be coming next.

Prince Harry was the happiest uncle in the world when he heard the news of Prince George’s birth in 2013. By his own admission, Harry saw himself visiting for daily play dates and quality time, but in his book, Spare, the Duke gave the impression that he had been essentially closed off by William and Kate and was “never invited” over.

“I took it for granted that I would be invited to their house at any moment. But the days went by, and it didn’t happen,” he explained. “I understand, I thought. They’re busy! Building a family! Or maybe… three’s a crowd. Maybe if I get married things will change,” Harry wrote in Spare.

Prince Harry’s relationship with Prince George, Princess Charlotte & Prince Louis

Two years later William and Kate welcomed Princess Charlotte, and Harry was able to create a bond with his nephew and niece. Prince Louis, though, was only two years old when the Duke left the UK behind, and it’s quite clear that the youngest of the Prince and Princess of Wales’ children doesn’t have any real connection to Harry.

That said, Harry has made it clear that he wants to be a part of the children’s lives. Not only that, but another sad part of his “exile” is that his children, Prince Archie and Princess Lilibet, have pretty much never seen their cousins.

As mentioned, Louis has never experienced the sort of relationship with his uncle Harry that his elder siblings did, simply because he was too young. But when the young prince was christened, Harry went to lengths to ensure he gave his youngest nephew a great present.

When Louis was christened, Harry put in plenty of work to get the perfect gift. Looking back, he remembered how his mother, Princess Diana, had a great passion for collecting first editions. Therefore, Harry wanted to start a new chapter with his nephews and nieces, thereby keeping the tradition alive.

Prince Harry on stage at the Clinton Global Initiative in New York
Craig Barritt/Getty Images for Clinton Global Initiative

“One of Harry’s happiest childhood memories was being read a bedtime story by his mother. She loved all the old classics, and Harry had the brilliant idea of starting a little library of first editions for Louis, Charlotte, and George to enjoy as they get older,” a close source told the Daily Record.

Prince Harry’s special gift to Prince Louis was inspired by his mother

Harry went shopping and bought an original edition of A. A. Milne’s Winnie the Pooh. It cost him about £8,000 ($10,000).

It was previously reported Harry opted for a rare copy from the initial print run of 30,000 copies in 1926.

“He originally wanted to get Lewis Carroll’s Through The Looking Glass, which was on sale for £24,000, but decided Winnie-The-Pooh would be more suitable for a first tome. Robinson Crusoe was William’s favorite book, but Harry loved all things A.A. Milne,” the source continued.

But while Harry undoubtedly adores his brother’s children, sadly, he also harbors concerns. In an interview with The Telegraph to promote his book, the Duke stated his worries about Princess Charlotte and Prince Louis becoming “spares” just like him.

“Though William and I have talked about it once or twice, and he has made it very clear to me that his kids are not my responsibility, I still feel a responsibility knowing that out of those three children, at least one will end up like me, the spare,” Harry said.

“And that hurts, that worries me.”

Prince William and Kate Middleton brings their children Prince George, Princess Charlotte and Prince Louis to school
Jonathan Brady – Pool/Getty Images

Harry continued: “I was brought into the world in case something happened to Willy, I was summoned to provide backup, distraction, diversion and, if necessary, a spare part. Kidney, perhaps. Blood transfusion. Speck of bone marrow. This was all made explicitly clear to me from the start of life’s journey and regularly reinforced thereafter.”

Prince William & Kate Middleton “aware” of possibly ‘Spare’ problems

At the time, royal expert Ingrid Seward criticized Harry for his words about Charlotte and Louis, saying he should” lay off Prince William’s children.” 

But even though Harry might have his worries, recent reports state that Prince William and Kate Middleton have everything under control. 

Speaking with the Mirror, royal expert Jennie Bond says that the Prince and Princess of Wales “must be acutely aware” of the problems that could come with Prince Louis — and Princess Charlotte — becoming “spare.”

“They have already shown that they have a different and modern attitude to bringing up royal children and I’m sure they will do everything to make Charlotte and Louis feel every bit as special, loved and valued as George,” Bond told the Mirror.

“I imagine they will encourage Louis to explore life outside the royal fold… it could be the military, but it could also be working in the charity world or whatever he finds appealing after his education is finished. I’m sure they will encourage him to go to University, which they both enjoyed and where, of course, they found love.”

Prince Louis sits in a wagon during Trooping the Colour.
Karwai Tang/WireImage

The royal expert continued: “And from there they will want him to find a life that is meaningful to him as well as appropriate for the son of a future King. They will try to ensure that he feels he is living a life of value, irrespective of his place in the line of succession and that will probably involve service of some kind as they have emphasised from the start that they want their children to understand that having empathy with others is not only a kindness, but is rewarding as well.”

Prince Louis could have ‘own career’ outside royal spotlight, expert says

As Bond suggested, William and Kate might encourage Louis to try new things and find his passion outside of royal life. Should he opt to remain in the royal fold, meanwhile, he will likely be handed a crucial senior role within the monarchy and significant titles.

But Bond isn’t the only one predicting that Prince Louis could do more than just royal engagements. In an interview with OK!, per Yahoo, Camilla Tominey, royal expert and associate editor at The Telegraph, claimed Prince William and Kate Middleton would want Charlotte and Louis to “have their own careers” if they’d prefer it.

“[William & Kate] don’t want history to repeat itself and Prince Louis seem like a royal hanger-on and go down the Duke of York path,” she told the Telegraph.

“A lot of the more minor royals have got careers of their own so they aren’t really being tax payer funded,” she continued. “The extent to which the Cambridges have tried to normalise the lives of their children very much points in the direction of – yes, Prince George has his destiny mapped out but Princess Charlotte and Louis’ having their own careers?’”

Prince Louis, Prince George, and Princess Charlotte waives to a crowd of people
Karwai Tang/WireImage

Tominey concluded: “They’ve got to get the balance right of what their own children want to do with their lives and their royal commitments.”

“We might be seeing fewer royals in the future than we’re used to. But the question is, are there going to be enough royals to go around?”

“In their family it would never be the ‘heir and spare’”

In an interview with Hello! Magazine, parenting expert Jo Frost said that the Prince and Princess of Wales would never allow Princess Charlotte and Prince Louis to become” heir and spare” to their older brother, Prince George. 

“I think William and Catherine understand the importance of nurturing the sibling relationships between the three of them,” Frost said.

“Dare I say it, in their family it would never be the ‘heir and spare’. It would be about the importance of all of them. The understanding that it really takes a team, with the important roles in upholding the crown and the monarchy.”

The relationship expert added: “And so, we’re seeing these very early seeds now, with respect to what it means to support each other and to nurture together.”

While Prince George and Princess Charlotte surely have recollections and great memories of spending time with Harry, Louis does not. Whether the kids know exactly why their uncle isn’t around anymore is unknown – but that could soon change.

Speaking to GB News, royal commentator Lydia Alty stated that the three royal children are ‘likely asking questions’ about Harry and what really happened when he left.

Prince Louis and his siblings are ‘likely asking questions” about Prince Harry

“Prince Harry used to be close to his brother, Prince William. He was also very close to Prince William’s wife, the Princess of Wales and their children, Prince George, Princess Charlotte and Prince Louis,” she said.

“Harry was even close to his father, despite reports and claims from him that he wasn’t. Now that the royals have all split up and, as far as we know, not talking, this will have affected George, Charlotte and Louis.”

Lydia Alty concluded: “His nephews and niece will probably be wondering why they haven’t seen their uncle and cousins.”

Do you think Prince Louis will become a working Royal Family member or move on to another career? Please share this article with friends and family and give us your opinion!

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