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

Who brings their parents on a first date? Well, my boyfriend from a dating app did—and they didn’t just show up, they came armed with an entire list of outrageous demands. It was clear I’d need to think on my feet.

I’d met Jacob on a dating app a few months back, and our chemistry seemed instant. He was different from the rest; every notification from him made my heart skip a beat. We had spent hours talking about our dreams, passions, even our vulnerabilities, and I’d grown to believe he was “the one.” But as reality would have it, when we finally met in person, my expectations didn’t just shift—they shattered.

Three months of late-night texts and hours of video calls had built up to this moment. Unlike most guys who opened with cheesy lines, Jacob had impressed me by recognizing my Scarlet Witch costume from Comic-Con in my profile picture. “Is that handmade? The detail is incredible!” he’d commented. Our conversations just flowed from there. He’d listened to my career dreams, connected over our shared love for true crime, and even opened up about his own experiences with anxiety when I mentioned my sister’s struggles.

When he suggested we finally meet in person, I was thrilled. I spent the week planning my outfit, picking a dress my best friend swore would make me “unforgettable.” The night finally arrived, and as I stood outside Coffee Beanz, I could hardly contain my excitement.

But when I walked in, my eyes met not only Jacob’s, but also those of an older couple sitting beside him, smiling as if this was entirely normal. My heart sank.

“Lia, over here!” Jacob called out, waving.

“Um, hi… what’s going on?” I asked, feeling like I’d walked into an ambush.

Jacob gestured to the couple. “These are my parents, Linda and Patrick. They insisted on meeting you.”

I awkwardly took a seat, but before I could even collect my thoughts, Linda—a petite woman whose diamond-studded earrings likely cost more than my rent—pulled a crisp paper out of her designer bag. She handed it to me with a smile that didn’t reach her eyes.

“We’ve prepared a few questions to get to know you better,” she said, clicking her gold pen.

I stared at the paper in disbelief. Each question was worse than the last:

• “What is your annual income and five-year career projection?”
• “List any medical conditions and family history of genetic disorders.”
• “Are you willing to sign a prenuptial agreement?”
• “Do you plan to work after having children, and if so, who will handle childcare?”

My water glass froze mid-air. “Is this… a joke?” I asked, trying to hide my disbelief.

“Of course not,” Linda replied, not skipping a beat. “Our family has certain standards. We must ensure Jacob’s partner is… suitable.”

I glanced at Jacob, hoping he’d jump in and say something, but he just sat there, studying his napkin as if it held life’s mysteries.

That was it. I wasn’t about to let them treat me like I was applying for a job. With a newfound confidence, I excused myself, heading to the convenience store next door. When I returned five minutes later, I sat back down and pulled out my own piece of paper.

“Before I answer your questions,” I said, smiling sweetly, “I have a few of my own.”

Linda’s expression faltered as she took the paper from me and read aloud, her face growing redder by the second:

• “At what point did you decide Jacob couldn’t choose his own partner?”
• “How many women have made it through this ‘interview process,’ or do they all run at the sight of your list?”
• “Will his future wife be required to submit weekly progress reports?”

“This is completely inappropriate!” she snapped, practically vibrating with outrage.

I leaned back, unfazed. “Inappropriate? You handed me a questionnaire as if I’m applying for a security clearance!”

Jacob finally looked up, mumbling something about how his parents were just “looking out for him.”

“No, Jacob,” I replied coolly. “What you need is to live your own life.”

Linda and Patrick, utterly insulted, began gathering their things. Linda announced they were leaving, but as they turned, I called after them. “Wait! Aren’t you forgetting something?”

“What?” she hissed, glaring over her shoulder.

“Waiter! These people are trying to leave without paying their bill!” I announced loudly, waving down the waiter. “Another proud family tradition?”

Linda’s hands shook as she reluctantly handed over her credit card, the entire restaurant now watching. I tossed five dollars on the table for my water and stood, turning to Jacob.

“Good luck finding someone who meets your family’s standards, Jacob. Maybe try job recruitment sites—they do background checks.”

That night, I received a message from Jacob: “You didn’t have to be so cruel. My parents were only trying to look out for me.”

I replied simply: “Just looking out for myself. Goodbye, mama’s boy.”

Later, my friend Sarah called to hear about the date. When I finished telling her, she was silent before saying, “I bet Linda has a spreadsheet ranking all of Jacob’s potential wives.”

We both burst into laughter, and as the last of my disappointment faded, I realized I’d just dodged a massive red flag.