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
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
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
“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
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
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
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
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
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
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
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
“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
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
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
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
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.
My Newly Adult Daughter Almost Married an Old Man, I Was Shocked until I Found out the Truth – Story of the Day
My 18-year-old daughter fell in love with a 60-year-old man and was marrying him against my wishes. She claimed she was madly in love with this guy. I was shocked when I discovered a chilling truth about him.
The late afternoon sun bathed the living room as I sifted through mundane mail, the doorbell’s chime announcing Serena’s early arrival from her part-time job. She breezed in, her vibrant presence filling the space with energy and the scent of vanilla. I eagerly waited for this time of the month when she’d visit me.
“Hey, Dad! You won’t believe what happened with my roommate, Jessica…” Serena paused, sensing my unease. “Everything okay?”
“Yeah, yeah,” I said. “Everything’s great. Come on in, honey.”
“So,” I began, “you were saying…”
For illustration purposes only | Source: Pexels
“Yeah, Dad. Actually…I met someone, and he’s like all nice and caring. Edison. Really loves me. We want to get married. But he’s…”
“But?”
“He’s sixty.”
The word ‘sixty’ hit me hard. My daughter, eighteen, with a man sixty — almost thrice her age? Concern and disbelief clouded my judgment. “Sixty, Serena? That’s… can’t you see the issue here?”
“Age doesn’t define love, Dad. Edison understands me, believes in me.”
“But what about the future, Serena? He’s much older.”
“Love isn’t about numbers, Dad. It’s about feeling seen, loved, cared for, and Edison makes me feel that way,” Serena’s voice trembled with conviction. “Please, can you at least meet him once? Trust me, you’ll love him.”
For illustration purposes only | Source: Pexels
I was shocked beyond words. Was Serena not realizing what she was talking about? Yet, I couldn’t refuse her. After all, what harm could a meeting do? I agreed to meet this Edison guy.
The next night at Edison’s, I needed a breather and went to the balcony. That’s when a snatch of conversation caught my ear. “Annie, come on now,” Edison’s voice, smooth and practiced, appeared. “I’m your brother. You know me well. It’s just a bit of harmless fun. A chance to win a little something extra.”
“This is reckless, Edison,” a woman’s voice, probably Annie’s, chided Edison. “You’re toying with that girl’s affections for some ‘harmless fun.'”
A cold dread twisted inside me. “What are you talking about?” Edison barked.
“The bet, Edison,” Annie hissed. “You think marrying a naive girl is easy money to clear your debts?”
My heart sank. Edison was using my daughter just for a bet. I was furious.
For illustration purposes only | Source: Getty Images
I rushed back in and found Serena. “Serena, we’ve been fooled! It’s all a game to him!” I blurted out.
“Dad, what are you talking about?” Serena looked so confused and then shocked as I told her about the bet.
“He’s lying to you, Serena! He’s just using you,” I said, my voice cracking.
But Serena got defensive. “You’re making this up! You never liked Edison! Edison cares for me…unlike you, Dad. You were never around. After Mom passed, it was like you chose your job over me. I felt alone, not like I had a dad. I didn’t need those nannies and expensive boarding schools, Dad. I needed you.”
Her words stung, but I knew we had to deal with Edison’s deception first.
Then, I saw him entering the dining room. Edison. I just couldn’t contain myself any longer. I lost it and punched him in the face, yelling, “Stay away from her daughter, you creep!”
For illustration purposes only | Source: Pexels
But Serena was furious with me. “Stop it, Dad! It’s my life, not yours!” she yelled, pushing me back. I knew no matter what I said at that moment, Serena would not take my side. She was blinded by the fake love Edison had shown her.
I eventually left, heartbroken but not beaten. I had to save my daughter. So, I called a buddy of mine who’s a private investigator. A few days later, he gave me a report about Edison’s dark past of failures and gambling addiction.
This was my shot to show Serena the truth about Edison and get her back.
The report mentioned Duke R., Edison’s old business partner, who got left in the dust because of Edison’s mess-ups.
The report said Duke hung out at a place called Le Beans Café, a little diner outside of town. I grabbed the phone number listed for Duke and called him up.
For illustration purposes only | Source: Pexels
At Le Beans Café, under its dim lights, I met Duke. Life had been tough on him, but he was ready to spill everything about Edison’s gambling issues. He wanted to help me keep my daughter safe from Edison.
After meeting Duke that night, I went to Edison’s favorite casino, pretending to be “Parker,” a rich guy from Texas. I looked the part and had my story ready. Sitting down at Edison’s table, I smiled.
“Welcome, Parker. Big game tonight. Feeling lucky?”
I played my cards right, literally, and ended up winning with a royal flush, beating Edison’s hand. He tried to keep calm, but I could tell he was rattled.
“Looks like beginner’s luck,” Edison snarled.
For illustration purposes only | Source: Pexels
“Or maybe some of us just know how to play,” I said, smiling slowly as I let him realize who I was. “Surprised to see me, Edison?”
He went white, finally getting what was happening. “Billy? What’s this about?”
“It’s about Serena. Leave her alone, and we’re square,” I said firmly, not giving him a choice. “Or,” I added, “you can settle the debt right now. In cash. And let’s just say, I have some… unconventional methods of collecting outstanding debts.”
“Fine, I’ll stay away from her,” he said reluctantly.
I left the casino feeling like I’d won but also worried. Edison gave in too easily, and I couldn’t shake the feeling that this wasn’t the end of it with Serena.
For illustration purposes only | Source: Pexels
The next morning, fury surged through me as Serena’s voicemail played yet again. Why aren’t you answering my calls, honey? Desperation led me to call her friend, Sarah, who cheerfully informed me of Serena’s engagement party to Edison, a piece of news that left me reeling.
“Engagement party? With Edison?” I was shocked.
“Yes! Didn’t Serena tell you? You should come, Mr. Thompson. It’s at The Grand Springs, starts at eight,” Sarah replied, oblivious to my shock.
Arriving at The Grand Springs, I was met with the sight of Serena, radiant with happiness, and Edison, oozing charm among the guests. My heart raced as I approached Edison, my anger peaking.
“We need to talk, now,” I said, pulling him to the side.
“Now? During the party?” Edison smirked, but I wasn’t having it and dragged him into a quiet bathroom to have it out.
For illustration purposes only | Source: Getty Images
“You think you can just waltz in and take my daughter’s life?” I accused, pressing him against the wall.
“She loves me. And your dirty little secrets? They could destroy you,” Edison shot back, hinting he knew things about me that could hurt me.
“But you’re not going to get her. Not on my watch!” I said, even though his threat to tell Serena about my past mistakes left me rattled.
“Two minutes, Thompson. Then I call security,” Edison warned, leaving me in turmoil. “You think you can stop this, Daddykins? She loves me. She wants me. And if you try anything, if she sees even a tiny scratch on me, she’ll turn her back on you forever. Is that what you want, Thompson? To be abandoned by your sweet daughter?”
No matter how much I hated that old creep, I had to admit he was right. Serena was already against me. I couldn’t afford to lose her forever.
For illustration purposes only | Source: Pexels
Defeated and heartbroken, I ended up outside, the bright city lights seeming to laugh at my inability to save Serena from Edison’s lies. I sat down on a bench, overwhelmed and hiding my face in my hands.
While I was lost in my own sadness, a cough caught my attention. Looking up, I saw a woman standing there, tall and with gray hair, looking kind of gentle in the faint light. “You’re Mr. Thompson, right?” she asked quietly.
“Annie? Edison’s sister?” I was surprised to recognize her.
She gave a small smile. “Yes, we’ve seen each other before… At Edison’s, when you tried to save your daughter,” she reminded me.
I quickly told her all about the mess with Edison and how he was tricking Serena. “And you’re aware of it, too, right?”
For illustration purposes only | Source: Getty Images
“That conniving weasel,” Annie finally spat. “He’s wasted everything — our inheritance, my savings from years of theatrical performances… all gone to feed his gambling addiction.”
“We could stop him,” I said, feeling she might want to help.
“What do you have in mind?” Annie asked.
I explained my plan to her and even offered her some money as a start. “Consider this a start,” I said.
“I’m listening,” she said, interested.
So, we went ahead with our plan at the wedding. Annie was there pretending to be just another guest. Right as Edison was putting the ring on Serena’s finger, a young woman stood up and yelled, “He’s a liar!”
For illustration purposes only | Source: Pexels
Then another woman stood up, telling her story about Edison’s lies. More people started speaking up, all exposing Edison’s evil deeds.
Edison tried to deny it. “No, they’re lying! I don’t even know them,” he said, but he was falling apart as everyone saw his true colors.
Our plan worked. The wedding turned into a place where all of Edison’s lies were laid bare for everyone to see.
In a moment filled with tension, an older woman approached Serena.
“Don’t fall for his tricks, dear. He’s nothing but trouble. Get away from him while you can! I’ve been a victim, too,” the woman said firmly. Watching through a video call, I saw Serena’s world fall apart as she threw her wedding ring away, her dream of happiness shattered.
For illustration purposes only | Source: Getty Images
This was the climax of the plan I had made with Annie and her group of actors to show everyone who Edison really was. Serena ran out of the church, clearly hurt, but it was the only way to save her from a terrible mistake.
Then, things got even more serious when the police showed up to arrest Edison, making it clear he was finally going to face the consequences of his actions. Although it cost me a lot to get Annie’s help, seeing my daughter free from Edison was worth every penny.
When I met Serena at her place later, it was a very emotional moment. “Dad, I’m so sorry. I should’ve listened to you,” she cried.
I held her and showed her a plane ticket to Boston, to remind her of her dream of studying fashion design. “It’s time to start over, to chase your dream,” I told her.
For illustration purposes only | Source: Pexels
She looked at me, grateful and hopeful. “Thanks, Dad. I love you,” she said.
This whole ordeal reminded me how important it is to be there for our kids and to do whatever it takes to keep them safe.
If only I’d been there for Serena, she’d never have fallen for someone like Edison. I had learned a huge lesson and decided to make my daughter my priority.
Tell us what you think about this story, and share it with your friends. It might brighten their day and inspire them.
Leave a Reply