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.
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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.
“And when Cherise and I get married, I’ll buy her a house, and naturally, you’ll need one nearby too,” I continued. The two of them were practically salivating at the thought. I had them hooked. Claire started fantasizing about a house by the beach, while Cherise envisioned a walk-in closet and gourmet kitchen. They were so wrapped up in their dreams, they didn’t notice what was coming next.
Dropping the Bombshell & The Panic Sets In
“Just one small thing,” I said casually, “You’ll need to meet my other wives first. They have to approve before we move forward.” The atmosphere at the table shifted in an instant. Their wide eyes and stunned expressions were priceless.
“Other… wives?” Claire stammered, while Cherise could barely get a word out. I nodded, keeping a straight face. “Yes, I have two other wives. They’re wonderful women, and I expect at least five children from you, Cherise.”
The Perfect Exit, Walking Away Victorious
As they sat there, speechless and horrified, the bill arrived. Claire looked at me expectantly, but I leaned forward with a grin. “In my culture, we believe in women showcasing their strength and independence. You can take care of this bill.”
I stood up, left cash for my portion of the meal, and walked out of the restaurant with a smirk. Behind me, I heard them scrambling, their voices filled with outrage. The cool night air felt refreshing as I walked to my car.
The Sweet Taste of Victory – A Lesson Learned
What started as a simple first date had turned into an unexpected challenge. But instead of letting them take advantage of me, I turned the tables and left them stunned. The satisfaction I felt was worth more than any fancy dinner or gift.
That night taught me a valuable lesson: sometimes, the best way to deal with entitled people is to give them a taste of their own medicine. This bizarre first date will be a story I tell for years, not just for the laughs, but for the reminder of my own strength and wit.
Conclusion: Outplaying the Players
Life has a funny way of teaching lessons when you least expect them. And on that night, I learned that the best way to handle people trying to take advantage is to stay sharp—and maybe, just maybe, turn the tables.
Sources
- “My Date Brought Her Sassy Mom on Our First Date and She Started Interrogating Me — I Decided to Outplay Them” Amo Mama. Caitlin Farley. July 26, 2024.