Who Brings Their Parents to a First Date? My Boyfriend Did—And They Came Armed with a List of Outrageous Demands
When I swiped right on Jacob months ago, I had no idea what I was signing up for. We connected instantly, trading messages that made my heart race and convinced me he might be the one. It felt like a modern fairytale—until reality crashed the party.
Picture this: I show up to our first in-person date, excited to finally meet the guy who seemed so perfect online. But instead of just Jacob, he brought a plus two. His parents. Yes, you read that right—his parents tagged along to our first date.
But that wasn’t even the craziest part. They came armed with a list of demands—outrageous ones at that. It was as if they were interviewing me for a position I didn’t even apply for!
I knew in that moment I’d need to think fast. If I was going to survive this bizarre interrogation, it had to be on my terms, not theirs. What followed was a game of wits, one I never thought I’d have to play on a first date.
Let me tell you, sometimes reality has a way of completely shattering those perfectly crafted illusions we build online. But one thing’s for sure—this story is one for the ages.
A woman holding a phone | Source: Unsplash
Three months of late-night texts and hour-long video calls had all led to this moment. Jacob wasn’t just another swipe; he felt like something more.
While most guys opened with cheesy pickup lines or the dreaded “hey,” Jacob stood out immediately. His first message wasn’t generic — it was specific, thoughtful, and impossible to ignore.
“Is that a handmade Scarlet Witch costume?” he’d asked about my Comic-Con photo. “The detail work is incredible!”
From that moment, our conversations clicked effortlessly. Jacob wasn’t just interested; he was engaged. He didn’t just nod along when I talked about my work as a graphic designer—he truly listened. He asked questions about my dreams of starting my own studio and shared ideas that inspired me.
For three months, I’d started to believe he was everything I’d been looking for. But nothing could’ve prepared me for what was waiting when we finally met in person.
A woman using a computer | Source: Midjourney
Jacob wasn’t just a great conversationalist; he shared my love for true crime podcasts and could quote every episode of my favorite shows by heart. When I opened up about my sister’s battle with depression, he surprised me by sharing his own struggles with anxiety.
“I feel like I can tell you anything,” he said during one of our video calls, his warm brown eyes crinkling as he smiled. “I’ve never connected with someone like this before.”
“Me neither,” I admitted, feeling my cheeks flush with a mix of excitement and vulnerability. “Sometimes I worry this is too good to be true.”
He laughed softly, running a hand through his dark hair in that effortlessly charming way. “It’s real,” he reassured me. “I can’t wait to finally meet you in person. Friday at Coffee Beanz? 7 p.m.?”
It felt like the start of something special—until Friday arrived, and my idea of Jacob was turned completely upside down.
A man using a laptop | Source: Pexels
“It’s a date! Finally!” I’d chirped, barely able to contain my excitement.
“See you on Friday,” he said with a grin, his voice lingering in my mind long after the call ended. I hung up, cheeks flushed and heart racing.
The entire week became a blur of preparation. I spent hours debating outfits before finally settling on a stunning dress that my best friend, Sarah, swore made my eyes pop.
“He won’t know what hit him,” she teased, expertly curling my hair and giving me a playful nudge.
By Friday evening, I was a bundle of nerves, standing outside Coffee Beanz and smoothing my dress for what felt like the hundredth time. Through the window, I could see couples chatting over coffee, their laughter floating out into the crisp evening air. Soft candlelight flickered across their faces, and I could almost picture myself and Jacob sitting among them.
This was it—the moment I’d been waiting for. But nothing could’ve prepared me for what was about to happen next.
People in a cafe | Source: Unsplash
My hands trembled slightly as I pushed open the heavy wooden door, greeted by the warm aroma of garlic and fresh bread wafting through the air. My heart pounded in anticipation as my eyes scanned the room, searching for Jacob.
“Lia! Over here!”
I turned at the sound of his familiar voice, my practiced smile already in place—until it froze mid-expression.
There he was, but he wasn’t alone.
An older couple sat beside him, their faces lit up with cheerful smiles. My heart, once buoyant with excitement, plummeted to the pit of my stomach.
“Hey… um, hi, what’s going on?” I stammered, forcing the words out as my brain scrambled to make sense of the unexpected scene.
Jacob stood and gestured toward the couple like he was introducing honored guests. “Lia, meet my parents! They insisted on joining us tonight.”
I blinked, utterly dumbfounded. This was not the first date I had envisioned.
A shocked woman | Source: Pexels
Jacob stood up, his bright smile unwavering, as if this was the most natural thing in the world. “Lia, I’m so excited to finally meet you! These are my parents, Linda and Patrick!”
Linda, a petite woman with impeccably styled gray hair and gold earrings that likely cost more than my monthly rent, gave me a tight, polished smile that stopped just short of her eyes. Patrick, meanwhile, was absorbed in the menu, barely sparing me a glance, his dress shirt stretched just a little too snug across his chest.
“Sit down, girl,” Linda said, patting the chair beside her—not the one next to Jacob. Her tone was sweet, but the words carried the weight of authority.
I hesitated, glancing toward Jacob for some sort of explanation, but his grin remained fixed, oblivious—or maybe complicit.
“While we wait for our appetizers,” Linda continued, folding her hands neatly on the table, “I have a few questions for you.”
The confidence I’d carefully built up all week evaporated in an instant. This was no date—it was an interview, and I was the candidate under scrutiny.
An older lady smiling | Source: Midjourney
I sank into the chair, my pulse racing as I tried to process what was happening. The waiter arrived with water glasses, but all I could think was how much I needed something stronger—preferably something strong enough to make this situation disappear.
Before I could catch my breath, Linda reached into her sleek designer handbag and pulled out a crisp sheet of paper, laying it on the table with all the authority of a CEO presenting a quarterly report.
“Now then,” she said, her voice carrying the same cool professionalism. With a deliberate click of her gold-plated pen, she pushed the paper toward me. “I’ve prepared a brief questionnaire to help us get to know you better. Please fill it out.”
My jaw dropped. A questionnaire? For a first date?
I turned to Jacob, desperate for him to step in and defuse this surreal situation. But instead of intervening, he gave me an awkward shrug, his sheepish smile silently saying, It’s fine—just go with it.
I glanced back at the paper, its crisp edges gleaming under the candlelight like some twisted contract. My cheeks burned as the once-cozy ambiance of the café turned stifling.
This wasn’t the charming dinner I’d spent all week dreaming about. It was an interrogation. And as I sat there frozen, I wrestled with the growing urge to grab my coat and make a break for the door.
Sheets of paper on a table | Source: Pexels
My eyes scanned the paper, each question hitting me like a slap to the face. It was less of a questionnaire and more of a highly invasive interrogation.
- What is your current annual income and five-year career projection?
- Please list any medical conditions, including a family history of genetic disorders.
- How many romantic partners have you had, and what were the reasons for those relationships ending?
- Do you own or lease your vehicle? What is your credit score?
- Are you willing to sign a prenuptial agreement?
- Do you plan to work after having children? If so, who will provide childcare?
- What is your stance on living with in-laws?
- Are you willing to host special occasions like Thanksgiving and Christmas every year without expecting a penny from your partner?
I blinked at the paper, struggling to keep my jaw from hitting the table. This wasn’t a simple “get-to-know-you” exercise—it was a full-blown screening process for a potential corporate merger, complete with clauses and contingencies.
I stole a glance at Jacob, who still wore that awkward smile, as if this was totally normal. My mind raced. Was this some kind of twisted test? A prank? Or worse—a glimpse into what life with him and them would be like?
I swallowed hard, my fingers twitching at the edges of the paper. One thing was clear: this wasn’t the dreamy romance I’d been imagining. It was a nightmare in designer heels.
A startled woman covering her mouth | Source: Pexels
The questions kept coming, an endless parade of absurdity that left me reeling. My water glass froze halfway to my lips as I stared at Linda.
“I’m sorry, but… is this for real?” I finally managed, my voice laced with disbelief.
“Of course it is, dear,” Linda replied smoothly, her tone oozing with condescension. She folded her hands primly on the table, her gold-plated pen still poised as if ready to jot down my answers. “Our family has certain standards to maintain. We need to ensure that any potential partners for our Jacob are… suitable.”
Suitable. The word hung in the air like a bad smell.
I turned to Jacob, praying he’d say something—anything—to stop this madness. But he just sat there, intently studying his napkin like it contained the secrets of the cosmos.
My stomach sank. This wasn’t just a quirky family tradition or a misunderstanding. This was real. And Jacob wasn’t about to lift a finger to stop it.
A man sitting casually | Source: Midjourney
Something inside me snapped. Three months of late-night texts, shared dreams, and deep conversations—and now, I was being treated like a job applicant. I could feel the tension building in my chest, threatening to boil over. No. This wasn’t happening.
I took a deep breath, forcing a sweet smile. “Would you excuse me for just a moment?” I said, as calmly as I could. “Ladies’ room.”
Linda gave me a polite nod, barely sparing me a second glance.
But instead of heading to the restroom, I made a beeline for the convenience store next door. My heart pounded in my chest as I grabbed a small notebook and pen, something that would give me the upper hand in this twisted game.
Five minutes later, I returned, striding back into the café with a new sense of purpose. I sat down, straightening my back, and met Linda’s expectant gaze with a cool smile.
“Before I answer your questions,” I said, my voice steady and confident, “I have a few of my own.”
This was no longer about answering their invasive questions. It was about reclaiming control of the situation.
A woman holding a piece of paper | Source: Pexels
Linda’s perfectly plucked eyebrows shot up in surprise as I slid my notebook onto the table, my questions now front and center. She picked it up, her eyes scanning the words, her face morphing from disbelief to outright fury.
She began reading aloud, her voice sharp and accusing, as if to make sure everyone at the table knew just how outraged she was.
“Question one: At what point did you realize your son wasn’t capable of choosing his own partner?”
Patrick’s face turned a deep shade of crimson. Jacob finally looked up from his napkin, his eyes wide with something between guilt and confusion.
“Question two: How many women have actually completed your interrogation process? Or do most run screaming before the credit check?”
Linda’s voice pitched higher with each word as she read, her fury now palpable. “This is completely inappropriate!” she hissed, her face flushing with indignation.
I leaned back in my chair, arms crossed, watching the chaos unfold. It felt like the first real victory of the evening.
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?”
The room had gone completely still, the tension so thick you could cut it with a knife. Linda’s lips were trembling with fury, Patrick was avoiding eye contact, and Jacob… well, Jacob was suddenly standing, his face a mixture of shock and anger.
“That’s enough!” Jacob’s voice broke through the silence like a thunderclap as his hand slammed down on the table. The silverware rattled, and I could see the veins in his neck bulging. “You have no right to disrespect my family like this!”
For a brief moment, I felt the weight of his anger, but then I straightened up, unfazed. This was my stand, my boundary, and I wasn’t backing down.
An angry man | Source: Midjourney
I leaned back in my chair, crossing my arms, refusing to be intimidated. “Oh, but they have every right to treat me like I’m applying for a position at the FBI?” I shot back, my voice steady and clear.
Jacob opened his mouth to speak, but his words were weak, almost pleading. “My parents are just looking out for me,” he protested. “They want what’s best—”
“No, Jacob.” I cut him off, my tone firm, unyielding. “What’s best for you would be growing a backbone and living your own life. It’s time to stop letting them control your every move.”
The air around us grew thick with tension, and I could feel the weight of their judgment as Linda and Patrick began gathering their things. Their faces were flushed with indignation, their composure slipping. Linda’s hands trembled as she hastily stuffed the questionnaire back into her bag.
“We’re leaving,” she declared, her voice trembling with frustration. “Jacob, come on. She’s not the one for you.”
I didn’t flinch. I didn’t move. The decision was made. Whatever came next, I was done with the games.
“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, their eyes wide in disbelief. “WHAT??”
I grinned, not giving them an inch. “Waiter, these people are trying to leave without paying their bill!” I announced loudly, my voice carrying across the suddenly silent room. “Guess running out on checks is another proud family tradition!”
The entire restaurant had gone still, everyone turning to look at the spectacle. Linda’s hands shook as she fumbled for her credit card, practically throwing it at the waiter in a flurry of frustration.
I stood up, smoothing my dress with a calm that felt like the only thing in control in that chaotic moment.
“Well, this has been entertaining,” I said, my voice dripping with sarcasm. “I’ll cover my water.” I placed a five-dollar bill on the table and turned to Jacob, offering him a final glance.
“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.”
With that, I walked away, leaving them in stunned silence behind me.
A woman laughing | Source: Midjourney
As I stepped 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 rolled my eyes and quickly typed back, “Just looking out for myself, mama’s boy. Goodbye!”
Later that night, Sarah called to hear about the disastrous date. I recounted every detail, still in disbelief. She was quiet for a moment, digesting the chaos.
“You know what?” she finally said, her voice filled with amusement. “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 in that moment, I was more grateful for a red flag wrapped in a questionnaire than I’d ever been for anything else.
A woman walking away | Source: Midjourney
After a long day at work, I staggered through the door, too exhausted to think straight. I threw my bag on the couch, changed into something comfortable, and collapsed into bed, desperate for some rest. The noise of the world outside faded, and I quickly drifted off into a deep sleep.
Hours later, I jolted awake, disoriented. The room was pitch black, save for the faint moonlight filtering through the blinds. I rolled over to check the time, but my eyes froze on the figure lying next to me.
The man sleeping beside me wasn’t my husband.
My heart slammed against my chest as panic surged. I tried to slow my breathing, rubbing my eyes to clear the fog. But the face—his face—was still there. His broad shoulders, the mess of dark hair, the outline of his body pressed against the sheets… I didn’t recognize him.
I lay there, frozen in place, wondering if I was still dreaming. But no, this was real. I could feel the cool touch of the sheets against my skin, the weight of the situation sinking in. The stranger beside me stirred slightly, his breath slow and steady, unaware of my panic.
In a daze, I glanced around the room, trying to piece together how I ended up here. The familiar decor, the scent of my husband’s cologne lingering in the air… everything felt wrong. Had I brought someone home in a sleepwalking stupor? But no, I was certain I hadn’t.
I quietly slipped out of bed, careful not to wake him. My mind was racing, trying to form a rational explanation for the situation, but nothing made sense. What was happening? Where was my husband?
Then it hit me like a brick. The realization made my stomach drop: I had no idea who this man was, and I didn’t remember inviting him into my home.
I reached for my phone, my hands shaking as I searched for the number I needed. My fingers hovered over the screen, but nothing felt right. The room spun, and I took a step back, the weight of the moment sinking in deeper than ever.
This story is inspired by real events and people, but 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.
