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.

10+ Mistakes Every Parent Should Avoid for Their Child’s Financial Future

Fearing for their children’s futures, parents search for universal parenting techniques that will put their kids on the route to a prosperous job and a happy life. But times are changing, and the old principles of success are no longer relevant. Sometimes, parents’ actions, intended to be helpful, can actually create challenges for their children’s future.

1. Not allowing their kid to fail

Perfectionist parent often strives for perfection themselves, leading them to expect increasing levels of perfection from their child as they grow older — from the child’s artwork never being good enough to their bed not being made perfectly or not studying hard enough. The child faces constant criticism and reprimands but is never allowed to learn from their mistakes. Children of perfectionist parents may grow up to be perfectionists themselves or develop low self-esteem and lack confidence. Both outcomes can negatively impact their future careers.

  • Anna’s mother always compared her to Mary, saying, “Look how tidy Mary is compared to you, Anna!” Despite Anna’s efforts to emulate Mary, she never measured up, and her mother’s criticism only intensified. Anna’s mother never allowed her the chance to improve her habits and learn basic skills. Now at 25 years old, Anna still compares herself to others and always comes up short in her own eyes. Needless to say, this constant comparison has taken a toll on her self-esteem.

2. Paying a child for good grades

This topic remains a subject of debate, but consider this perspective: imagine yourself as a contractor continually paying more for a product or service, with the child as the supplier providing it in exchange for money or rewards. It doesn’t sound like a good idea, does it?

  • Alexandra’s parents sought to motivate their daughter to excel in her studies by offering money as an incentive. Initially, Alexandra’s grades improved, suggesting the approach was effective. However, her parents later discovered that she had been fabricating stories about an imaginary illness and sharing them with her teachers. She even falsely claimed that her parents constantly criticized her for poor grades. The sympathetic teacher then raised Alexandra’s grades out of pity. Following this incident, Alexandra’s parents discontinued the practice of paying for grades and sought guidance from a child psychologist.

3. Preventing their child from expressing their feelings

Sometimes, adults dismiss a child’s feelings as wrong — insisting that bruises don’t hurt, feeling anger toward a child who hit them is shameful, or being sad even with a valid reason is incorrect. Parents often do this with good intentions, wanting to teach their children proper behavior. However, it’s crucial to recognize that a fundamental skill for modern individuals is the ability to acknowledge and manage their feelings, emotions, and needs.

  • Kate, now 37, vividly remembers how her mother forced her to give away her beloved doll to another girl, admonishing her for being “greedy” and scolding her for getting upset over a “stupid toy.” Kate never got her doll back. Over the years, she has worked hard to assert herself, learning to say “no” to demanding people, including her boss and coworkers. Despite this, Kate often feels guilty whenever she refuses to comply with their requests.

4. Failing to support their child in front of strangers

Every child needs the assurance that their parents will stand up for them in any conflict, regardless of the situation, and won’t blindly trust the words of authority figures like teachers, principals, or neighbors. When parents allow their children to speak up for themselves when they are ready to take responsibility for their actions, it helps them develop healthy self-esteem and a sense of personal accountability.

  • Maggy was raised by her grandmother, who often said, “But what will other people think?” Although her grandmother loved Maggy and wanted the best for her, she constantly emphasized the importance of public opinion. As a result, Maggy struggles to make her own decisions and even relies on her friends’ opinions when choosing something as simple as dessert.

5. Drawing inspiration and comparing to successful people

Each generation has its own set of heroes whom young people aspire to emulate. In recent decades, the tales of personal success from wealthy and influential individuals have become widespread. However, it’s not as simple as learning their life story and achieving happiness. If it were that easy, everyone who reads their books would have solved all their financial problems by now.

  • Alex developed a passion for computers from a young age. Inspired by the story of Steve Jobs that his dad shared with him, Alex immersed himself in learning everything about Apple. When it came time to choose a university, Alex initially believed he didn’t need higher education because Steve Jobs succeeded without it. Eventually, Alex realized the importance of education for his path and pursued college to advance his career. Now, Alex jokes, “What worked for Steve Jobs is just a waste of time for an ordinary guy like me.”

6. Pressuring their child to decide on their future career

The notion that a person should stick to one career for their entire life is likely outdated and impractical. Many modern occupations didn’t exist a decade ago, while others have already become obsolete.

  • Since childhood, Max had a passion for exploring computers and understanding various software programs. Despite his parents’ concerns, he pursued this interest and eventually discovered online courses in software testing. Now, he is thriving in this field, leveraging his potential and skills.
  • Laura, at 37, worked as a sociologist for a major consulting firm but found it challenging to maintain her career after having her son. During maternity leave, she rediscovered her love for photography. Starting with unique photos of her child, Laura progressed to offering photoshoots for friends’ and acquaintances’ kids. Over time, she opened her photo studio. Laura now earns as much as her husband and successfully manages her professional life while caring for her family. This shift exemplifies the evolving nature of careers and the importance of embracing new opportunities.

7. Arguing about money

Since children may absorb long-lasting messages from these circumstances, it’s crucial to avoid arguing about money or other matters in front of them. Instead of one-on-one conflicts, which can cause youngsters to take sides and become distressed, talks should be led in a way that promotes involvement.

  • Chris grew up witnessing his parents argue about money. When he went to college at 17 and moved away, he struggled with managing his finances and spending on unnecessary items. He now fears starting relationships, believing that money is the root cause of his sadness.

8. Prohibiting the child from using social networks

Social networks have become today’s equivalent of the yards and neighborhoods where we used to play as children. Kids can learn valuable skills through computer programs integrated with social media platforms. While parents should remind their kids about online safety rules, depriving children of this experience can be harsh.

  • Aria’s mother was surprised to discover that her 10-year-old daughter had learned to create cool videos. Even more surprising was the realization that Aria had learned this skill from using TikTok. Now, creating short videos has become a family hobby for them.

9. Teaching the kid that they have the stuff at home

Many of us recall times when we asked our parents to buy us things, only to hear, “We already have that at home; we don’t need it.” Some parents repeatedly expose their children to such situations, unintentionally discouraging them from getting what they truly need. This pattern can significantly impact their financial habits as adults. On the other hand, constantly satisfying a child’s every need can also have negative effects.

  • Jan’s mother often tells him they have things at home and they don’t buy them from the store. Jan has learned to overlook his needs, and with each subsequent request, he withdraws more, knowing not to ask. When Jan grows up and earns his income, money will go towards trivial things because that’s how he’s learned to live.

10. Preventing children from getting into conflicts

The ability to engage with others is perhaps one of the most crucial professional skills one can possess. It’s important not only to help children make friends but also to teach them how to engage in healthy arguments. People often hold differing opinions, and there are various ways to express emotions. The sooner children grasp this concept, the easier their interactions with others will be, including in professional settings.

  • Michaela spent her life avoiding conflicts, preferring to agree with others rather than engage in disputes. She believed that someone always had to be the “smarter” one, but this approach proved more harmful than beneficial. One day, Michaela learned about active listening and decided to apply this approach in her professional life. She excelled at paying attention to others’ perspectives while also expressing her feelings when others attempted to take advantage of her. Initially, people found her communication style unconventional, but conflicts with coworkers became more constructive, leading to mutually beneficial resolutions.

11. Helping their child learn to save money

The world is always changing, and old ways of making or saving money might not work anymore. We can’t predict what skills will be valuable in the future economy. That’s why it’s important to teach kids to be flexible and ready for change, not just to save money.

  • Emily’s grandfather saved money his whole life “just in case.” But when that “case” finally happened, a financial meltdown made all his investments lose value. Emily saw this while growing up, and now she’s worried the economy could collapse at any time. She believes the best investment is in her skills and knowledge.

12. Trying to build a strong character with the help of sports

While there’s a widespread belief that sports are beneficial for discipline and character development, excessive competitiveness in professional sports can be detrimental to a child’s physical and mental health. This competitiveness can be fueled by both fellow young athletes and coaches. Only a few individuals become champions, and coaches often prioritize these select few, neglecting the rest of the team. Coping with this unfair treatment at a young age can lead to low self-esteem and confusion about alternative life paths if a child must stop playing sports.

  • Tom’s mother pursued rhythmic gymnastics as a child but had to abandon her Olympic dreams due to a leg injury. When Tom was three, his mother enrolled him in gymnastics classes, hoping he would excel. However, Tom struggled in this sport, leading him to lose interest in school, feel like a failure, and struggle to identify his strengths. Now, Tom is studying to become a child psychologist to help parents navigate the challenges of raising children without making the same mistakes.

Being protective of your children is natural, but it’s important to set boundaries. Respecting their privacy is crucial for a healthy parent-child relationship and their personal development. Violating their privacy can have serious negative effects, especially on their mental health.

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