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

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When Ronny set up a date with Denise, he was hoping for a fun and laid-back evening, just the two of them getting to know each other. What he didn’t expect was for Denise’s mother, Claire, to show up and tag along. As the night unfolded, Claire’s endless questions and extravagant demands hinted at something much deeper. But Ronny, thinking fast, found a hilarious way to turn the tables on both of them.

I’d been on dating apps for a while, dealing with one disappointing date after another. But this one? This one truly took the cake.

Denise and I matched a couple of weeks ago, and we hit it off right from the start. She seemed sweet, charming, and even said my silly jokes made her laugh. We exchanged a few messages, and I decided to ask her out. We agreed to meet at a trendy downtown restaurant that Saturday.

I was genuinely excited about this one. I showed up early, like always, wanting to make a good impression. The atmosphere was perfect—soft lighting, sleek decor, and a pleasant buzz of people chatting all around me. I imagined everything going smoothly… until Denise walked in, with her mother right beside her.

My heart sank like a stone.

“Hey, Ronny! This is my mom, Claire!” Denise chirped, acting like bringing her mom along was the most normal thing in the world.

I forced a smile, hiding my shock and confusion. “Hi, nice to meet you,” I managed to say.

Claire, dressed to impress with an air of authority, shook my hand firmly. “Hello, Ronny. Hope you don’t mind me joining you two tonight.”

“Oh, not at all,” I lied, baffled by what was going on. Was this some sort of test? A safety measure?

We took our seats, and Claire wasted no time taking over the conversation. “So, Ronny, what do your parents do?” she asked, her tone sharp and probing.

I cleared my throat, feeling like I was in an interrogation. “My mom’s a retired teacher, and my dad was an engineer.”

She gave a curt nod, then quickly fired another question. “And where do you live? Do you rent or own?”

“I own a small house,” I answered, trying to keep my cool, though I felt more like I was at a job interview than on a date.

Claire wasn’t done. She kept grilling me—about my job as a business analyst, my income, and my plans for the future. I glanced at Denise, hoping she might rein her mother in, but she just sat there smiling, like this was all part of the plan. That’s when it hit me: I was being sized up for something, and it wasn’t for love.

Claire leaned back, studying me with a calculating look. “You seem like a good match for Denise, Ronny. Just so you know, we’re accustomed to a certain lifestyle, and it takes money to maintain that.”

Before I could even respond, she tapped the menu. “Oh, and we’ll be having the lobsters. You’re paying, right?”

I was stunned—not just by Claire’s boldness but by Denise’s silence. It was clear now. They weren’t interested in me; they were interested in what I could provide.

But then, an idea sparked in my mind. If they wanted to play games, I was game.

I plastered a big smile on my face. “Absolutely! Lobster it is. I’m all for living large. And you know what, Claire? This is the perfect chance to talk about my future plans with Denise.”

Claire’s eyes lit up with interest, and Denise leaned in, curious.

“You see,” I went on, “I have several investments that bring in millions every year, so money’s no issue. And I believe in taking care of family. Claire, once Denise and I get married, I’ll buy you a house near ours. Denise will definitely need help with the kids.”

Denise’s eyes widened, and Claire looked like she had just hit the jackpot.

“Really? That’s so generous of you, Ronny!” Claire gushed. “I’ve always dreamed of a beach house.”

I nodded, still grinning. “Oh, don’t worry. You’ll get your dream house, right next to ours. But of course, there’s one thing we have to sort out first.”

Claire leaned forward, eagerly. “What’s that?”

I paused dramatically, then said, “You’ll need to meet my other wives first. They have to give their approval.”

The table went dead silent.

“Other wives?” Claire blurted out, her confident smile slipping.

Denise looked like she might faint. “Wives? Plural?” she stammered.

I nodded seriously. “Oh, yes, I have two other wives. Wonderful women. We have a big family—lots of kids. In fact, some of them were getting a bit spoiled, so we had to send them to foster families. But don’t worry, Claire, you’ll fit right in.”

The looks on their faces were priceless. Claire’s jaw dropped, and she seemed to be at a loss for words.

Denise’s voice trembled as she asked, “Ronny, why didn’t you mention this before?”

I shrugged casually. “Didn’t seem relevant until now. But since we’re talking about marriage and kids, I figured you should know.”

By the time the check came, Claire was fuming. “You’re paying for dinner, right? After all, you’re so wealthy,” she snapped.

I grinned back. “Actually, in my culture, women show their independence by paying for their own meals. I wouldn’t want to deny you that opportunity.”

Their faces flushed with outrage as I calmly put down some cash for my own meal and stood up. “It was a pleasure meeting you both. Enjoy the lobster.”

As I walked out of the restaurant, I couldn’t help but chuckle. I had turned their shallow game back on them, and it felt great.

What started out as a disaster of a date ended up being one of the most entertaining nights I’d had in a long time. Sometimes, the best way to deal with people trying to use you is to give them a taste of their own medicine.

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