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

When Ronny met Denise for their first date, he didn’t expect her mother, Claire, to tag along. As the evening progressed, Claire’s intrusive questions and lavish demands revealed a much deeper motive. But Ronny, quick on his feet, hilariously turned the tables on them both.

I’d been on dating apps for a while, experiencing a string of underwhelming dates, but this one truly took the cake.

Denise and I matched a couple of weeks ago, and we hit it off right away. She was sweet, charming, and said my goofy jokes actually made her laugh. After a few exchanges, I asked her out, and we set up a date at a trendy downtown restaurant.

I was excited—more than usual. I arrived early, as I always do, wanting to make a good impression. The ambiance was perfect—soft lighting, modern decor, and the faint hum of conversations around me. I imagined the evening going smoothly… until Denise walked in with her mother.

My heart sank.

“Hey, Ronny! This is my mom, Claire!” Denise said brightly, as if bringing her mother along was the most natural thing in the world.

I forced a smile, doing my best to hide my confusion. “Hi, nice to meet you,” I said.

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

“Of course not,” I lied, inwardly baffled by the situation. Was this a safety precaution? Was Denise testing me?

We sat down, and Claire wasted no time taking control of the conversation. “So, Ronny, what do your parents do?” she asked, her tone sharp.

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

She nodded, then quickly followed up. “And where do you live? Do you rent or own?”

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

Her questions kept coming—about my salary, my job as a business analyst, and my future plans. I glanced at Denise, expecting her to rein in her mother, but she just sat there, smiling. I realized that this was no ordinary dinner—it was a setup, and I was the main course.

Claire leaned back in her chair and gave me a scrutinizing look. “You seem like a good match for Denise, Ronny. We’re used to a certain lifestyle, and it takes money to maintain that.”

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

I was stunned, not just by Claire’s presumptuousness but by Denise’s lack of reaction. It was clear now—they were only interested in what I could provide financially.

Suddenly, an idea sparked in my mind. If they wanted to play games, I was more than happy to join in.

I smiled broadly. “Absolutely! Lobster it is. I’m all about living large. And since we’re talking about the future, I’m glad you’re here, Claire. This is the perfect time to discuss my plans for Denise.”

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

“You see,” I continued, “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 widened. Claire was practically salivating.

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

“Oh, don’t worry,” I said, keeping a straight face. “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 forward eagerly. “What’s that?”

“Well,” I said, pausing dramatically, “you’ll need to meet my other wives. They have to approve first.”

The atmosphere at the table froze.

“Other wives?” Claire stammered, her confident facade cracking.

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

I nodded. “Oh yes, I have two other wives. Wonderful women. We have a big family—lots of kids. In fact, some of them were 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 of horror on their faces was priceless. Claire was speechless, her jaw working silently as she tried to process what I’d just said.

Denise, on the other hand, was trembling. “Ronny, why didn’t you mention this before?”

I shrugged. “Didn’t seem relevant until now. But since we’re discussing marriage and children, I thought you should know.”

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

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

Their faces flushed with indignation as I calmly placed 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 help but chuckle. I had managed to turn the tables on their shallow demands, and it felt great.

The evening may have started as a disaster, but I ended up getting the last laugh. Sometimes, the best way to deal with people trying to take advantage of you is to give them a taste of their own medicine.