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

When Ronny meets Denise for their first date, he’s shocked to find her mother, Claire, tagging along. Over dinner, Claire’s intrusive questions and expensive demands reveal their true intentions. But Ronny, quick-witted and unfazed, hilariously turns the tables on them both.

I’ve been on dating sites for a while and have been on a couple of dud dates. The one I’m going to tell you about really takes the cake!

Denise and I matched a couple of weeks ago, and we instantly hit it off. She’s sweet and charming, and she says my stupid jokes make her laugh. It didn’t take long for me to ask her on a date.

We both have busy schedules but last weekend, they finally aligned. We planned to meet at this trendy, upscale restaurant downtown.

I was so excited. I arrived early, as always. It’s a habit of mine, wanting to be the first one there to make a good impression. As I waited, I took in the ambience—dim lighting, modern decor, the soft murmur of conversations around me. Perfect setting for a promising first date.

Then she walked in. But she wasn’t alone.

Next to her was an older woman, stylishly dressed, with a sharp gaze that could probably cut through steel. My heart sank a little.

“Hey, Ronny! This is my mom, Claire!” Denise said with a big smile.

“Hi, nice to meet you,” I replied, hiding my shock as best I could.

Claire shook my hand with a grip that screamed authority. “Hello, Ronny. I hope you don’t mind me joining you two tonight.”

“Of course not, the more the merrier,” I lied through my teeth, my mind racing.

My mind was doing cartwheels, trying to figure this weird situation out. I wondered if it was a test, but then I started thinking she’d brought her mom as backup, in case I turned out to be a creep. Fair enough. Nobody can be too careful these days.

We sat down, and immediately, Claire took control of the conversation.

“So, Ronny, where do your parents work?” she asked, her eyes fixed on me like a hawk on a mouse.

I cleared my throat. “Uh, my mom’s a teacher and my dad’s an engineer. They’re both retired now, though.”

“Interesting. And where do you live? Are you renting, or do you own your place?” she continued, not missing a beat.

“I stay in a small house,” I replied, starting to feel like I was on a job interview rather than a date.

“And what do you do for a living? How much do you make?” Claire’s questions were rapid-fire, each one more invasive than the last.

I glanced at Denise, hoping for some support, but she just smiled and nodded, seemingly okay with her mom’s interrogation. Great.

I cleared my throat. “I already told Denise what work I do.”

Denise nodded and promptly turned to her mom and said, “Ronny’s a business analyst.”

Claire gave an approving nod, then leaned forward and looked me in the eye. “You seem like a good match for my Denise, Ronny. You see, we’re accustomed to living well and enjoying the little luxuries in life. For this, money is a must!”

“I guess so,” I replied. I was starting to see the bigger picture, but what she said next left me speechless.

“We want these lobsters, by the way.” Claire leaned back and tapped her finger on the menu. “It’s your treat, right?”

I looked at Denise, certain that this would be the point where she told her mom to back off. Instead, she just smiled at me.

Well, this wasn’t going at all how I’d planned! Claire was clearly only interested in my money and Denise… she could just as well have been a statue at that point.

I was almost in despair, trying to keep my composure. Then, a mischievous idea sparked in my mind.

If they wanted to play games, why not have some fun?

I smiled broadly. “Oh, absolutely! Lobsters it is! I’m all about living the good life and I can see now that you’re here for a serious discussion about your daughter’s future with me, right ma’am?”

“She likes you very much, Ronny, and I need to ensure you’ll provide her with the sort of lifestyle she deserves,” Claire replied.

“I certainly will. I earn millions every month from some investments my dad made for me when I was a kid so money is no object,” I said.

Claire’s eyes lit up, and Denise’s jaw dropped. It took every ounce of self-control to keep a straight face as I continued my ludicrous lie.

“And I’ll take care of Denise if we get married. She’ll have to look after our children so she won’t have time to work anyhow. I’m sure she’ll want help from her mom, so I will, of course, buy you a home close to ours.”

They exchanged a look that was half disbelief, half excitement. I had them hook, line, and sinker.

“Wow, Ronny! That sounds incredible. Denise, did you hear that? A separate home just for me!” Claire gushed, practically salivating at the thought.

Denise’s eyes sparkled as she leaned closer. “Ronny, you’re too kind. I can’t believe how lucky I am!”

I grinned, inwardly relishing the build-up to my grand reveal. “Oh, absolutely. I believe in living lavishly and taking care of family.”

Claire and Denise exchanged looks, their imaginations undoubtedly running wild with visions of luxury. Claire, now more animated, began planning aloud.

“You know, I’ve always dreamed of a house by the beach. Somewhere sunny, with a big garden and space for entertaining. Maybe even a pool,” Claire mused, her voice dripping with anticipation.

Denise chimed in, “And I’d love a walk-in closet and a gourmet kitchen. Oh, Ronny, this is amazing!”

I kept my expression earnest, nodding along. “That sounds perfect. Of course, you’ll need to meet my other wives first. They have to give their approval before we can take our relationship to the next level.”

The atmosphere at the table shifted instantly. Claire’s smile froze, and Denise’s jaw dropped.

“Excuse me, what did you just say?” Claire’s voice had an edge now, sharp and incredulous.

“Other… wives?” Denise echoed, her voice trembling slightly.

I nodded, maintaining a serious demeanor. “Yes, I have two other wives. They’re wonderful women. We have a big family. Unfortunately, some kids were too spoiled and had to be placed in foster families, but I expect you to have at least five children, so it’ll balance out.”

The color drained from their faces. Claire’s eyes widened in horror, while Denise looked like she might faint.

“Five children?” Denise whimpered.

“This… this is a joke, right?” Claire stammered, her confidence shattered.

“No, not at all. It’s quite the lifestyle, really,” I said, trying to suppress my laughter at their reactions. “You’ll love it.”

Denise’s voice quivered. “Ronny, why didn’t you mention this before?”

I shrugged nonchalantly. “It didn’t seem relevant at the time. But now, with all this talk of houses and future plans, I thought it was important to be honest.”

Claire’s horror turned to anger. “This is outrageous! How could you lead us on like this?”

I leaned back, crossing my arms. “I wasn’t leading anyone on. Just sharing my life. If you’re serious about joining our family, these are things you need to know.”

When the bill arrived, Claire eyed it and then glared at me. “Ronny, you’re paying, right? After all, you earn millions.”

I smiled, leaning forward. “Oh, in my culture, women value their strength and independence. So, I want to give you this opportunity to showcase those qualities. I can’t pay for you.”

Their faces were a mix of outrage and confusion. Denise’s hands shook as she grabbed her purse, while Claire’s indignation was palpable.

“You’ve got to be kidding me!” Denise finally burst out, her voice rising.

“Nope, not at all. This is your chance to prove your independence and strength,” I replied, standing up and placing some cash for my meal on the table. “It was lovely meeting you both.”

As I walked away, I couldn’t help but chuckle. Behind me, I heard them scrambling to gather their things, their flustered voices rising in the once-serene restaurant.

Outside, the cool night air felt refreshing. I took a deep breath, reflecting on the evening. It had started as a promising first date but turned into something entirely different.

I had faced an unexpected challenge and managed to outwit them, turning the tables on their entitled behavior. It felt good.

It wasn’t just about the small victory over Claire and Denise, but the realization that I had stood up for myself. I hadn’t let them take advantage of me, and I’d done it in a way that left them stunned and embarrassed.

Sometimes, the best way to deal with entitled people is to turn the tables on them. Denise and Claire learned that trying to manipulate someone for their money can backfire spectacularly.

It was an epic first date that I’ll never forget, and a valuable lesson in standing up for oneself.

As I walked to my car, I couldn’t stop grinning. This would be a story to tell for years to come. Not just because it was bizarre and hilarious, but because it reminded me of my own strength and wit.

Life has a funny way of teaching us lessons when we least expect them. And that night, I learned that the best way to handle people who try to take advantage is to give them a taste of their own medicine.

The satisfaction I felt from outplaying them was more valuable than any fancy dinner or expensive gift could ever be.

Click here to read how Tom discovered the guy his wife was cheating on him with was paying half their bills, and how his plan to cash in on it almost led him to ruin.

This work is inspired by real events and people, but it has been fictionalized for creative purposes. Names, characters, and details have been changed to protect privacy and enhance the narrative. Any resemblance to actual persons, living or dead, or actual events is purely coincidental and not intended by the author.

The author and publisher make no claims to the accuracy of events or the portrayal of characters and are not liable for any misinterpretation. This story is provided “as is,” and any opinions expressed are those of the characters and do not reflect the views of the author or publisher.