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 Best Friend Couldn’t Watch Our Prom Tape with Me and My Boyfriend But When I Saw What He Did, Everything Clicked — Story of the Day
Pam thought the reunion of high school friends would be a simple trip down memory lane. But when an old prom tape emerged her curiosity deepened. As the tape began to play, the grainy footage revealed something that left Pam questioning everything she thought she knew about those close to her.
Caleb and I stood at the front door, the crisp evening air brushing against my face.
My heart thudded with a mix of excitement and nervousness. I glanced at Caleb, whose expression screamed indifference.
His hands were stuffed into his jacket pockets, and his shoulders slouched like he’d rather be anywhere else.
“You could at least pretend to be excited,” I said, my voice tinged with irritation.
“Pam, not now,” Caleb muttered, rolling his eyes. “Can we not start this here? Just give me a couple of hours without the drama, okay?”
For illustration purposes only. | Source: Midjourney
“Drama? Seriously?” I shot back, crossing my arms.
“I’m not asking for much. I just want you to care about something that’s important to me.”
“There you go again,” he sighed heavily.
“Look, I’m here, aren’t I? I could’ve been at the pub with the guys, but I came. That should count for something.”
“If hanging out at the pub means more to you than our little high school reunion, you might as well go,” I snapped, my voice sharper than I intended.
For illustration purposes only. | Source: Midjourney
“School reunion? There would only be three of us!” Caleb retorted, his frustration bubbling over. “You always twist my words. It’s like you don’t even try to understand me.”
Before I could respond, the door creaked open, revealing Connor, his face lighting up with a warm smile.
“Pam! Caleb! You made it!” he said, his voice full of genuine enthusiasm. “Sorry for the delay. You know, last-minute prep.”
“Connor!” I beamed, wrapping him in a friendly hug. I reached into the bag I was holding and pulled out the cake I’d spent the afternoon baking.
For illustration purposes only. | Source: Midjourney
“Look, I brought a cake.”
Connor’s eyebrows shot up in surprise.
“Oh wow! You baked this? That’s amazing, Pam!”
“Yep,” I said, feeling shy under his admiration. “It’s a special occasion.”
“Twenty years since we graduated… Crazy how time flies,” Connor said, examining the cake with a grin.
“Yeah, yeah. She baked a cake. Big deal,” Caleb interrupted with a groan.
For illustration purposes only. | Source: Midjourney
“Can we go inside now? I’m freezing out here.”
Connor chuckled, stepping aside. “Of course, come on in.” As I walked past, Connor gave me an encouraging smile, a silent but comforting acknowledgment.
Connor had always been my best friend, the kind of person who got me without needing explanations.
He had a way of making me feel seen, even when others didn’t.
As Caleb trudged ahead, his disinterest almost tangible, I couldn’t help but notice the contrast between the two.
For illustration purposes only. | Source: Midjourney
Connor led us to the living room, his usual warm demeanor setting a welcoming tone.
Caleb, however, made a beeline for the couch, grabbed the remote, and started flipping through channels like he was in his own living room.
I stood there for a moment, hands on my hips, watching him settle on a sports network.
“Caleb, seriously?” I said, my voice laced with frustration.
“Can’t you watch that game later?”
For illustration purposes only. | Source: Midjourney
He didn’t respond, his eyes glued to the screen as if my words were background noise. It was one of his go-to moves—pretend I wasn’t upset, and eventually, I’d let it go. Annoyingly, it often worked.
Sighing, I let my attention wander to an open cabinet in the corner of the room.
Inside was a box overflowing with old items—photos, trinkets, and memories that seemed to be calling my name.
On top was a photo album. My curiosity got the better of me, and I knelt to pull it out.
For illustration purposes only. | Source: Midjourney
Flipping through the pages, I felt a rush of nostalgia.
The photos captured moments from our high school days—laughing faces, awkward hairstyles, and the kind of carefree energy I hadn’t felt in years.
A bittersweet smile tugged at my lips, and I could feel tears threatening to form.
“Caleb, come here!” I called out, holding up a photo. “It’s us on that school trip! Remember?”
“Can you not? You’re interrupting,” Caleb said flatly, still glued to the TV.
For illustration purposes only. | Source: Midjourney
Before I could snap back, Connor walked in carrying plates of cake. His eyes landed on the album in my hands, and his face lit up.
“You found the old photos,” he said, setting the plates down.
“My mom loved taking pictures. She was convinced we’d thank her someday.”
He straightened his posture and mimicked a stern voice.
“‘You’ll thank me when you’re older!’ she’d always say.”
For illustration purposes only. | Source: Midjourney
I laughed. “She sounds like she was a gem.”
As I flipped to another page, something caught my eye—a VHS tape sitting in the box beneath the album. Its label, scrawled in marker, read “PROM.”
“You have prom footage?” I asked, holding up the tape.
Connor hesitated. “Oh, that? It’s ancient. Probably doesn’t even work anymore. Besides, who has a VCR these days?”
“Right there,” I said, pointing to the dusty player next to the box.
For illustration purposes only. | Source: Midjourney
Connor sighed, his shoulders slumping slightly. “I forgot that was even there…”
“Caleb, we need the TV!” I called over my shoulder.
Caleb didn’t even glance up. “Touch this TV, and I’ll snap that tape in half,” he said, his tone low and firm.
“Fine!” I huffed, turning to Connor with determination. “You have a TV in your room, right? Let’s go.”
Connor looked uneasy, but he nodded, leading the way.
The promise of seeing that prom footage ignited a spark of excitement in me, even if Caleb couldn’t care less. Something told me this tape held more than just old memories—it held answers.
For illustration purposes only. | Source: Midjourney
I rushed into Connor’s bedroom clutching the VHS tape like it was a treasure chest.
My heart was racing, not just from excitement but from a strange mix of nostalgia and curiosity. Connor followed behind me, looking as if he’d rather be anywhere else.
“I’m telling you, Pam, this is a bad idea,” he said, rubbing the back of his neck. His unease was written all over his face.
“Bad idea?” I repeated, scoffing as I crouched to plug the VCR into the small TV in his room.
For illustration purposes only. | Source: Midjourney
“Connor, this is the best idea I’ve had all night. Come on, don’t you want to relive prom? This is history, our history.”
Connor sighed heavily, crossing his arms. “I just think some things are better left in the past.”
“Not this,” I insisted, sliding the tape into the player. “This is gold. Ready? Here we go!”
As the tape whirred to life, the screen filled with the grainy, slightly distorted image of Connor’s mom holding a camcorder. Her voice came through loud and clear, cheerful and commanding.
“Connor, smile! It’s prom night!” she chirped from behind the camera.
For illustration purposes only. | Source: Midjourney
Young Connor appeared on the screen, a boy trying to fit into a man’s suit.
His hair was slicked back with too much gel, and his bright red tie was slightly crooked. He looked like he wanted to disappear.
“Mom, stop filming,” he groaned, shifting uncomfortably under her gaze.
“You’ll thank me when you’re older!” she shot back with a chuckle.
I burst out laughing. “Wow, she really said that! You weren’t kidding.”
For illustration purposes only. | Source: Midjourney
Connor didn’t share my amusement. “Pam, I’m serious. Let’s just stop this.”
Ignoring him, I leaned closer to the screen as the tape transitioned to a car ride. The camera jostled slightly, showing the interior of the vehicle and Connor in the passenger seat.
“Mom! Stop the car! Pull over!” young Connor suddenly shouted.
“What’s wrong?” his mom asked, the camera swinging to catch his panicked expression.
“It’s Pam,” he said, pointing out the window. “She’s crying.”
For illustration purposes only. | Source: Midjourney
The camera panned to a younger version of me, sitting on the porch of my house, my face buried in my hands. I remembered that night all too well.
Caleb had been late, and I’d convinced myself he wasn’t coming. I was heartbroken, ready to skip prom entirely.
“I’ll go ask her to prom, I’m ready to tell her about my feelings,” Connor said softly.
His mom’s voice was full of warmth. “My little prince. Go ahead.”
The footage showed Connor stepping out of the car, straightening his tie as he approached. But before he could reach me, another car pulled up.
For illustration purposes only. | Source: Midjourney
Caleb stepped out, his dad giving him a light shove to hurry him along.
I looked up, my tear-streaked face breaking into a radiant smile when I saw Caleb. Without hesitation, I ran to him, leaving Connor standing alone in the driveway.
The camera caught every moment—my joy, Caleb’s smug grin, and Connor’s heart sinking as he watched from afar.
I hit the pause button, my hand trembling. “Connor… You were going to ask me to prom?.. Even more, you were going to tell me that you loved me..”
He didn’t meet my eyes. “It doesn’t matter now, Pam. It never did.”
For illustration purposes only. | Source: Midjourney
“But all these years…” My voice cracked. “You cared about me?”
Connor finally looked at me, his expression pained but resolute.
“Of course I did. But you were happy with Caleb, and that’s what mattered. That’s all that ever mattered.”
Tears streamed down my face as I tried to process what I’d just seen and heard. “Why didn’t you tell me?”
Connor shook his head, giving me a sad smile. “Because you were already where you wanted to be. And I couldn’t ruin that.”
For illustration purposes only. | Source: Midjourney
The room felt heavy with unspoken words. I didn’t know what to say, and for once, Connor didn’t fill the silence.
We both stared at the frozen image on the screen, young Connor standing alone in the shadows while I walked away, blissfully unaware.
We returned to the living room, where Caleb was still glued to the TV, oblivious to everything. But something inside me had shifted.
I sat next to Connor, stealing glances at him as he pretended everything was fine. The memory of that night, of his quiet heartbreak, lingered in my mind.
For illustration purposes only. | Source: Midjourney
“Connor,” I whispered. “You’ve always been there for me. I see that now. You’ve always been more than a friend, haven’t you?”
“Pam, please,” he said, his voice breaking. “Let it go.”
I bit my lip, unsure of what to do. My heart was torn between the familiarity of Caleb and the quiet, unwavering love Connor had always shown me.
For illustration purposes only. | Source: Midjourney
“Maybe in another life,” I said softly.
“Maybe,” Connor replied, his smile bittersweet.
That night, I lay awake, wondering what could’ve been. For the first time, I questioned everything I thought I knew about love—and what it meant to be truly seen.
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