Man from Dating Site Brought His Parents on Our First Date with Their Ridiculous Demand – I Decided to Outplay Them

When I met Jacob on a dating site, I was captivated. He was charming, attentive, and seemed genuinely interested in who I was.

Our messages quickly turned into long, late-night conversations, and soon, I found myself thinking he might just be “the one.”

We had spent months getting to know each other over video calls and texts, sharing stories, dreams, and even insecurities.

Jacob felt different from other guys I’d dated. He noticed the details, like my handmade Scarlet Witch costume in a profile photo, and he remembered the little things about me.

I thought I knew him so well. But as our first date approached, I would discover there was a lot he hadn’t told me.

Friday evening, I arrived at Coffee Beanz with butterflies in my stomach, dressed in the perfect outfit my best friend Sarah had helped me pick out.

As I stepped inside, the warm aroma of coffee and pastries wrapped around me, and I scanned the tables for Jacob.

My excitement quickly faded when I spotted him—sitting with a well-dressed older couple who, I soon learned, were his parents.

“Lia! Over here!” he called, smiling as if nothing was out of the ordinary. I walked over slowly, processing the scene.

This was supposed to be a first date, not a family reunion. As I sat down, Jacob introduced his parents, Linda and Patrick. I forced a polite smile, trying to get a grip on the situation.

Linda patted the chair beside her, and as I sat, she reached into her designer bag and pulled out a sheet of paper, which she handed to me with a slight smile.

“Now, dear, I just have a few questions to help us get to know you better.”

I stared at the paper, my mind reeling. Each question was more invasive than the last:

  1. What is your current annual income and five-year career projection?
  2. Please list any medical conditions, including family history of genetic disorders.
  3. How many romantic partners have you had, and why did those relationships end?
  4. Do you own or lease your vehicle, and what’s your credit score?
  5. Are you willing to sign a prenuptial agreement?

And it continued from there, with questions about childcare, living arrangements, and hosting family holidays. I looked over at Jacob, expecting him to jump in and say this was all a joke. But he simply looked down at his napkin, avoiding my gaze.

“Is this…for real?” I asked, dumbfounded.

Linda looked at me with a slight frown, as if I were being difficult. “Of course, dear. We have to make sure our Jacob is in good hands. We’re just doing what’s best for him.”

I took a deep breath, deciding I needed a moment. “Would you excuse me?” I said, standing up.

Instead of going to the restroom, I ducked out to a nearby convenience store, grabbing a notebook and pen. Five minutes later, I returned to the table with my own list of questions, determined to flip the script.

I sat down, and with a calm smile, I slid my paper over to Linda. “Before I answer your questions, I have a few of my own.”

Linda’s face showed shock and then irritation as she scanned the page. I had written questions like:

  1. At what point did you realize your son couldn’t choose his own partner?
  2. How many women have gone through your interrogation process?
  3. Do you inspect their teeth, or is that saved for the second date?
  4. When Jacob moves out of your basement, will you require his future wife to submit weekly progress reports?
  5. Have you considered therapy for your control issues?

Linda’s face flushed, and she looked to Jacob for support, but he simply sat there, stunned. “This is outrageous!” she hissed, glancing around the restaurant as people started noticing the tension at our table.

“And treating me like a job applicant isn’t?” I asked, my voice low but firm. “Jacob, if you can’t stand up for yourself, that’s one thing. But don’t expect me to sit here and be treated like an acquisition.”

Jacob finally spoke up, his voice barely above a whisper. “My parents just want the best for me. They’re just looking out…”

I shook my head, standing up. “What’s best for you is to live your own life, Jacob, not let your parents run it.”

Linda, red-faced, started gathering her things, instructing Jacob to leave with her. But before they left, I raised my voice slightly. “Waiter!” I called out. “These people are trying to leave without paying their bill!”

Linda’s jaw dropped, and the entire restaurant went silent. She pulled out her wallet, her hands trembling, and angrily paid the check.

As I left the table, I turned to Jacob. “Good luck finding someone who meets your family’s standards. Maybe you should try a job recruitment site instead of a dating app. They’re much better at vetting.”

I walked out into the cool night air, my phone buzzing with a message from Jacob, saying, “You didn’t have to be so cruel. My parents were only trying to help.”

I typed back, “Just looking out for myself. Goodbye, Jacob.”

Later that night, I called Sarah, filling her in on the disaster. She laughed in disbelief and joked, “I bet Linda has a spreadsheet ranking all of Jacob’s potential wives.”

We both burst into laughter, and in that moment, all my disappointment melted away. If there was one thing I’d learned, it was that sometimes, dodging a red flag wrapped in a questionnaire is the best thing that could happen.

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