Date Gone Wrong: Her Sassy Mom Crashes Our First Date and I Outsmarted Them Both

I’ve been using dating sites for a while and have had my share of bad dates. But this one was the most unusual! Cherise and I matched a few weeks ago, and we hit it off instantly. She was sweet, charming, and really seemed to enjoy my jokes. It wasn’t long before I asked her out on a date.

After sorting out our busy schedules, we finally set a date to meet at a stylish, fancy restaurant downtown. I was excited to see if our connection would be as strong in person as it was online.

I got there early, hoping to make a good impression. The restaurant had a great atmosphere with its soft lighting, modern design, and quiet chatter. But then, Cherise walked in… with someone else. She was accompanied by an older woman, dressed sharply and looking quite intimidating.

“Hey, Charles! This is my mom, Claire!” Cherise said with a big smile. I was surprised but tried to hide it. Claire shook my hand firmly, showing she meant business. As we sat down, Claire got straight to the point.

She started asking questions quickly: “Where do your parents work? Do you rent or own your home? What’s your job?” It felt more like a job interview than a date. I looked at Cherise, hoping for some support, but she just smiled and seemed fine with her mom’s questioning. As the interrogation went on, I realized this was not going to be a usual date.

Then Claire made a surprising request: “We want these lobsters. It’s your treat, right?” I looked at Cherise, hoping she would step in, but she just smiled. It was clear this was their plan—see how much they could get from me. I felt my frustration rising, but instead of letting them get the best of me, I decided to play along and have some fun with it.

I flashed a big smile and said, “Of course! Lobsters it is. And since we’re discussing the future, I should mention that I make millions from investments.” Claire’s eyes widened, and Cherise’s jaw dropped.

“And when Cherise and I get married,” I added, “I’ll buy her a house, and of course, you’ll need one nearby too.” They were practically drooling at the idea. Claire imagined a house by the beach, while Cherise dreamed of a walk-in closet and a gourmet kitchen. They were so caught up in their fantasies that they didn’t see what was coming next.

“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 mood at the table changed immediately. Claire and Cherise were wide-eyed and speechless.

“Other… wives?” Claire stammered, while Cherise struggled to find her voice. I nodded, maintaining a serious expression. “Yes, I have two other wives. They’re great, and I expect at least five kids from you, Cherise.”

As they sat there, stunned and horrified, the bill arrived. Claire stared at me expectantly, but I leaned in with a grin. “In my culture, we believe in women showing their strength and independence. You can cover the bill.”

I stood up, left cash for my share of the meal, and walked out of the restaurant with a smirk. Behind me, I heard them scrambling and their voices filled with outrage. The cool night air felt refreshing as I made my way to my car.

What began as a simple first date quickly became an unexpected challenge. Instead of letting them take advantage of me, I flipped the script and left them in shock. 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 handle entitled people is to give them a taste of their own medicine. This bizarre first date will be a story I share for years, not just for the laughs, but as a reminder of my own strength and cleverness.

Life has a funny way of teaching us lessons when we least expect them. 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 on them.