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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, It’s my boyfriend from a dating app.

I’d met Jacob on a dating app a few months back, and our chemistry seemed instant. 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.

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.

Image for illustrative purpose only.

“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 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.”

Image for illustrative purpose only.

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.

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?”

Image for illustrative purpose only.

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.

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.”

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