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.

I met Jacob online several months ago, and sparks flew from our very first chat. Our connection seemed so genuine; every message from him was a delightful surprise. With time, I began to think he might be “the one.” But when we finally met in person, things didn’t quite go as I imagined.

Over three months, we exchanged countless late-night messages and embarked on hour-long video calls. Jacob was different from other guys; he commented thoughtfully on my interests, like the homemade costume I wore to Comic-Con.
“Is that a handmade Scarlet Witch costume?” he’d written to me. “The detail work is incredible!”
Our conversations were effortless. Jacob was genuinely interested in my career as a graphic designer and supported my dream of opening my own studio. He indulged in my love for true crime podcasts and could recite lines from my favorite shows with ease.

He was open and honest about his own struggles with anxiety, making me feel comfortable sharing my experiences as well. I felt like I could tell him anything. We decided to meet at Coffee Beanz on a Friday evening, a moment I eagerly anticipated.
I had spent the whole week deciding on my outfit, and with the confidence boost from my best friend Sarah, I was ready to meet him. As I stood outside the café, I took a deep breath, feeling both nervous and excited.
Inside, the place was cozy and inviting, filled with couples enjoying their meals. I noticed Jacob right away but with a big surprise — he wasn’t alone.

An older couple sat with him, and I felt my excitement plummet. Jacob introduced them as his parents, Linda and Patrick. They were polite but imposing, which intensified my confusion and disappointment.
Linda patted the chair next to her, inviting me to sit. Instead of Jacob being my date, it felt like I was there for an interview. Linda handed me a questionnaire that left me speechless. Questions about my income, family genetics, and marital expectations filled the page.
This was no ordinary first date. I felt like I was being judged for an invisible set of criteria that Jacob’s parents deemed essential. When I glanced at Jacob for support, he only seemed absorbed in his napkin.
Something changed in me. I excused myself, not to the restroom but to regroup. I quickly returned with my own list of questions designed just for Linda and Patrick.

Returning to the table, I placed my paper of questions in front of them. Linda read them aloud, her composure slowly unraveling. Questions mocking their helicopter parenting style filled her ears, and it wasn’t long before Patrick’s face turned red with embarrassment.
Jacob rose suddenly, defending his parents; his protest was weak and unconvincing. I pointed out how absurd it was to treat a date as though I needed their approval to live my own life.
Linda and Patrick gathered their things in a fit of anger. I called out to make sure they didn’t duck out on the check, leading to Linda paying hastily before they stormed out.
As they left, I paid for my water and bid Jacob farewell. The lesson was clear: I dodged a bullet wrapped in a red flag. Leaving with my head held high, I knew I had outwitted them on my own terms.
That evening, I took Jacob’s last message with a grain of humor. His family’s ridiculous standards weren’t my problem anymore. Sharing the story with Sarah over a call, we chuckled, realizing sometimes a misadventure can be a blessing in disguise.