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 decided to meet Denise for their first date, he expected a relaxed evening, maybe some good laughs and a chance to really connect with her. What he didn’t expect was Denise’s mother, Claire, to show up too. As the night went on, Claire’s pushy questions and extravagant demands showed that she had a hidden agenda.

But Ronny wasn’t going down without a fight. In fact, he was about to turn the situation around in the most unexpected way.

I’d been trying my luck with dating apps for a while now, and honestly, I was getting tired of boring dates that went nowhere. But this one… this one was different.

Denise and I had matched a couple of weeks ago, and from the start, we clicked. She was sweet, seemed genuinely interested, and told me my silly jokes actually made her laugh. After a few days of chatting, I asked her out, and we planned a date at a popular restaurant downtown.

I was more excited than I’d been in a while. I got to the restaurant early, as usual, wanting to set the right tone. The place looked great—soft lighting, sleek furniture, and a gentle hum of conversations filled the air. I pictured the evening going perfectly… until Denise walked in with her mother.

My stomach dropped.

“Hey, Ronny! This is my mom, Claire!” Denise said, all cheerful, like bringing your mom along on a first date was the most normal thing ever.

I managed to force a smile, though my mind was racing with confusion. “Hi, nice to meet you,” I replied, trying to sound upbeat.

Claire, dressed to the nines and clearly full of confidence, shook my hand firmly. “Hello, Ronny. Hope you don’t mind me joining you two tonight.”

“Of course not,” I lied, wondering what in the world was happening. Was this some kind of test? Was Denise nervous and needed backup?

We all sat down, and Claire immediately took over the conversation. “So, Ronny, what do your parents do?” she asked sharply, her eyes studying me like I was an item at an auction.

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

She gave a quick nod and fired off another question, “And where do you live? Do you rent or own?”

“I own a small house,” I replied, feeling more like I was being grilled for a job than having dinner with a potential date.

The questions kept coming—about my salary, my job as a business analyst, and my future plans. I glanced at Denise, hoping she’d step in and tone down her mom, but she just sat there, smiling as if nothing was wrong. That’s when it dawned on me: this wasn’t a normal dinner. I was being evaluated, and they wanted to know how much I could bring to the table—literally and figuratively.

Claire leaned back and gave me a hard 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.”

Before I could reply, she tapped the menu. “By the way, we’ll be having the lobsters. Your treat, right?”

I sat there, stunned by her nerve. Denise, meanwhile, remained completely unbothered. It was obvious—they were interested in my bank account, not me.

Suddenly, a brilliant idea popped into my head. If they wanted to play games, I was ready to give them the best performance they’d ever seen.

I put on my brightest smile. “Absolutely! Lobster it is. I love living large. And since we’re talking about the future, I’m so glad you’re here, Claire. This is the perfect time to discuss my plans for Denise.”

Claire’s eyes sparkled with interest, and even Denise leaned in, curious about what I was going to say.

“You see,” I began confidently, “I have several investments that bring in millions every year. So, money is never an issue for me. I also believe in taking care of family. Claire, once Denise and I get married, I’ll make sure to buy you a house near ours. After all, Denise will need help with the kids.”

Denise’s eyes grew wide, and Claire looked like she had hit the jackpot.

“Really? That’s so generous, Ronny!” Claire said, practically licking her lips. “I’ve always wanted a beach house.”

“Don’t worry,” I continued, keeping my face straight. “You’ll get your dream house, right next to ours. But, of course, there’s just one small thing we need to handle first.”

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

I paused for dramatic effect and then said, “Well, you’ll need to meet my other wives. They have to approve first.”

The entire table went silent, like someone had hit the pause button.

“Other wives?” Claire’s voice was shaky, her confident demeanor suddenly crumbling.

Denise looked like she was going to faint. “Wives? Plural?” she whispered, barely able to speak.

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 got a bit too spoiled, so we had to send them to foster families. But don’t worry, Claire, you’ll fit right in.”

The look on their faces was absolutely priceless. Claire was speechless, her mouth opening and closing like a fish gasping for air.

Denise was trembling, and her voice cracked as she asked, “Ronny, why didn’t you mention this before?”

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

When the bill arrived, Claire was fuming. “You’re paying for dinner, right? Since you’re so wealthy?” she snapped.

I grinned and replied, “Actually, in my culture, women show their independence by paying for their own meals. I wouldn’t want to take away that opportunity from you.”

Their faces turned bright red with anger as I calmly put cash on the table for my meal and stood up. “It was a pleasure meeting you both. Enjoy the lobster.”

As I walked out of the restaurant, I couldn’t stop a chuckle from escaping. I’d managed to turn their shallow little plan upside down, and it felt fantastic.

The night may have started off on the wrong foot, but in the end, I got the last laugh. Sometimes, when people try to take advantage of you, the best thing to do is give them a taste of their own medicine.

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