My Date Brought Her Sassy Mom on Our First Date and She Started Interrogating Me — I Decided to Outplay Them – a Short Story

I’ve been on dating sites for a while and have had my fair share of dud dates. But this one? This one takes the cake! Cherise and I matched a couple of weeks ago, and we clicked right away. She was sweet, charming, and seemed to genuinely enjoy my sense of humor. It didn’t take long for me to ask her on a date.

Planning the Perfect First Date & A Surprise Guest

After juggling our busy schedules, we finally found a night to meet at a trendy, upscale restaurant downtown. I was excited, eager to meet her in person and see if our chemistry was as strong in real life as it was online.

As always, I arrived early, wanting to make a good impression. The setting was perfect—dim lighting, modern décor, and the soft hum of conversations. But then, she walked in… with someone else. Next to her was an older woman, sharply dressed, with an intimidating gaze.

Read More: 10 Things To Help Adult Children Heal From Narcissistic Parents

Meet Claire, The Uninvited Guest – Interrogation Begins

“Hey, Charles! This is my mom, Claire!” Cherise introduced her with a big smile. I was taken aback but hid my shock as best as I could. Claire shook my hand with a grip that meant business. As we sat down, Claire wasted no time.

Her questions came fast and sharp: “Where do your parents work? Do you rent or own your home? What do you do for a living?” It felt less like a date and more like a job interview. Hoping for some backup, I glanced at Cherise, but she just smiled along, perfectly content with her mom’s grilling session. As the interrogation continued, I realized this wasn’t going to be a typical date.

A Shocking Demand & A Lightbulb Moment

Then Claire dropped a bombshell: “We want these lobsters. It’s your treat, right?” I looked at Cherise, expecting her to intervene, but she simply smiled at me. Clearly, this was their game plan all along—see how much they could get out of me. I could feel myself getting frustrated. But instead of letting them win, I decided to turn the tables. If they wanted to play, I’d play right along—and have some fun doing it.

The Game Begins With An Outlandish Offer

I flashed a broad smile and said, “Of course! Lobsters it is. And since we’re talking about the future, I should let you know that I make millions from investments.” Claire’s eyes lit up, and Cherise’s jaw dropped.