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 met Denise for their first date, he was ready for a nice evening, maybe some good conversation, and hopefully a chance to impress her. What he wasn’t ready for was her mother, Claire, showing up too. As the night went on, Claire’s constant questions and over-the-top demands revealed that she had something more on her mind.

But Ronny, ever the quick thinker, found a way to turn the tables on both of them in a way they never saw coming.

I’d been using dating apps for a while, and after a bunch of disappointing dates, I thought I’d seen it all. But this date… oh, this one was on a whole different level.

Denise and I matched a couple of weeks back, and we clicked immediately. She was sweet, had a great smile, and even said she liked my goofy jokes. After a bit of back-and-forth, I asked her out, and we decided on a trendy restaurant downtown.

I was more excited than usual, even a bit nervous. I got there early, as I always do when I really want to make a good impression. The place was perfect—soft lights, modern decor, and a nice, comfortable buzz of conversations all around. I imagined the evening going just the way I hoped… until Denise walked in. With her mom.

My heart did a little flip.

“Hey, Ronny! This is my mom, Claire!” Denise greeted me cheerfully, like it was totally normal to bring your mom to a first date.

I forced a smile, trying to hide how thrown off I felt. “Hi, nice to meet you,” I managed to say.

Claire, dressed sharply and exuding confidence, reached out to shake my hand. “Hello, Ronny. I hope you don’t mind me joining you two tonight.”

“Of course not,” I lied, feeling confused and a little suspicious. Was this some kind of safety measure? Or maybe a test?

We all sat down, and before I even had time to adjust to the situation, Claire jumped right in, taking over the conversation. “So, Ronny, what do your parents do?” she asked with a directness that felt like she was holding a clipboard and taking notes.

I cleared my throat, trying to stay cool. “My mom’s a retired teacher, and my dad was an engineer.”

Claire nodded, but she wasn’t slowing down. “And where do you live? Do you rent or own?”

“I own a small house,” I replied, feeling more like I was at a job interview than a date.

The questions kept coming—about my salary, my job as a business analyst, my plans for the future. I glanced at Denise, hoping she’d step in and calm her mom down, but she just sat there, smiling like this was all perfectly fine. That’s when it hit me: this wasn’t just a date. This was a setup, and I was the main course.

Claire leaned back in her chair and gave me a long, assessing look. “You seem like a good match for Denise, Ronny. Just so you know, we’re used to a certain lifestyle, and it takes money to maintain that.”

I opened my mouth to reply, but before I could say anything, she tapped the menu and added, “By the way, we’ll be having the lobsters. Your treat, right?”

I was shocked, not just by Claire’s audacity, but by how Denise didn’t say a word. It was clear—they weren’t interested in me. They were interested in my wallet.

Then, a thought flashed in my mind. If they wanted to play games, I could play too.

I grinned widely. “Absolutely! Lobster sounds perfect. I’m all about living large. And now that we’re talking about the future, I’m actually glad you’re here, Claire. This is the perfect time to discuss my plans for Denise.”

Claire’s eyes lit up, and Denise leaned in, suddenly more interested.

“You see,” I continued with a smile, “I have several investments that bring in millions every year, so money won’t be an issue. I also believe in taking care of family. Claire, once Denise and I get married, I’ll buy you a house near ours. After all, she’ll need help with the kids.”

Denise’s eyes got wide, and Claire looked like she was about to jump for joy.

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

I nodded seriously. “Oh, don’t worry. You’ll get your dream house, right next to ours. But of course, there’s something we need to get out of the way first.”

Claire leaned in closer, excited. “What’s that?”

I paused, savoring the moment. “Well,” I said slowly, “you’ll need to meet my other wives. They have to approve first.”

The table went completely silent.

“Other wives?” Claire stuttered, her confident facade crumbling.

Denise looked like she was going to pass out. “Wives? Plural?” she whispered.

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

The horror on their faces was priceless. Claire’s mouth opened and closed like a fish, trying to find words.

Denise’s hands were shaking. “Ronny, why didn’t you mention this before?”

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

By the time the waiter brought the bill, Claire was fuming. “You’re paying for dinner, right? Since you’re so wealthy?” she spat.

I couldn’t help but grin. “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 turned red with anger as I calmly put some cash on the table for my meal and stood up. “It was great meeting you both. Enjoy the lobster.”

Walking out of the restaurant, I couldn’t stop myself from chuckling. I had managed to turn their shallow demands back on them, and it felt incredible.

The evening might have started off as a complete disaster, but I definitely got the last laugh. Sometimes, the best way to handle people trying to take advantage of you is to play their game better than they do.