My Date Brought Her Sassy Mom on Our First Date and She Started Interrogating Me—So I Turned the Tables
When Ronny met Denise for their first date, he wasn’t expecting her mother, Claire, to tag along. What began as an awkward dinner quickly turned into a battlefield of probing questions and lavish demands. But Ronny, armed with quick wit and humor, outsmarted them both in the most hilarious way.
I’ve been navigating the dating scene for a while now, and I’ve had my fair share of underwhelming dates. But this one? This one takes the cake!
Denise and I matched online a couple of weeks ago. We hit it off right away—she was sweet and charming, and she laughed at all my dumb jokes. It wasn’t long before I asked her out on a date.
We both have hectic schedules, but last weekend, the stars aligned, and we made plans to meet at a trendy, upscale restaurant downtown. I was pretty excited. I showed up early, as usual, eager to make a good impression. The ambiance was perfect—dim lighting, modern decor, and the soft hum of conversations in the air. The makings of a great first date.
Then Denise walked in—but she wasn’t alone.
Beside her was an older woman, stylishly dressed, with a gaze sharp enough to slice through stone. My heart sank.
“Hey, Ronny! This is my mom, Claire!” Denise said with a big, cheerful grin.
“Hi, nice to meet you,” I replied, trying to hide my surprise.
Claire extended her hand, her grip firm and commanding. “Hello, Ronny. I hope you don’t mind me joining you tonight.”
“Of course not, the more the merrier,” I said, forcing a smile as my brain went into overdrive. Was this a test? Or was I just the unlucky guy caught in a mother-daughter tag-team?
We sat down, and it didn’t take long for Claire to take charge of the conversation.
“So, Ronny, where do your parents work?” she asked, her eyes locked onto mine like a predator stalking its prey.
“My mom’s a retired teacher, and my dad used to be an engineer,” I answered, feeling like I was being grilled for a job interview.
“And do you rent or own your place?” she continued, barely pausing for breath.
“I own a small house,” I said, already feeling the heat of her interrogation.
“What do you do for work? How much do you make?” she pressed on, her questions becoming increasingly invasive.
I glanced at Denise for some kind of support, but she just smiled along, seemingly unbothered by her mother’s behavior. Great.
I cleared my throat. “I told Denise already—I’m a business analyst.”
Denise nodded, confirming it to her mom. But Claire wasn’t satisfied yet. She leaned forward, her eyes narrowing. “You seem like a good match for my Denise. You see, we’re accustomed to living well, and money is an important part of that.”
I was starting to get the picture. And then Claire delivered the kicker: “We’d like the lobster, by the way. It’s your treat, right?”
I looked to Denise, expecting her to step in, but she just smiled again, clearly complicit in this whole setup. At that moment, I knew exactly what was happening—Claire was testing me, not for my character, but for my wallet.
I almost gave in to the absurdity of it all, but then an idea hit me. If they wanted to play games, I was ready to play along.
“Oh, absolutely! Let’s get the lobster!” I said with a broad grin. “I can see you’re serious about Denise’s future with me, right, ma’am?”
Claire leaned back, clearly pleased. “Very serious. We want to ensure Denise will live the lifestyle she deserves.”
“Well, I make millions from some old family investments, so money’s no issue,” I said, barely keeping a straight face.
Both Claire and Denise perked up, their eyes gleaming. I could almost hear the wheels turning in their heads.
“And of course, if Denise and I get married, she’ll be a stay-at-home mom. I’ll buy you a house near ours too, Claire, so you can help with the kids.”
Their excitement was palpable. Claire started dreaming aloud about her perfect beach house, while Denise went on about walk-in closets and gourmet kitchens. They had no idea I was stringing them along.
Then, with the perfect timing, I dropped the bombshell.
“Oh, but of course, you’ll have to meet my other wives first. They need to approve before we move forward.”
The air at the table turned ice-cold. Claire’s smile vanished, and Denise looked like she’d seen a ghost.
“Other wives?” Denise stammered.
“Yep, two of them. We’re one big, happy family,” I said, struggling not to burst out laughing.
Claire’s face twisted in disbelief. “Is this some kind of joke?”
“No joke,” I said, leaning in. “You’ll fit right in. And don’t worry, we’ll have plenty of kids. Five at least—enough to balance out the spoiled ones who didn’t make the cut.”
Denise and Claire looked like they were about to faint. Their plan had backfired spectacularly.
When the bill arrived, Claire glared at me. “You’re paying, right? After all, you’re a millionaire.”
I leaned forward with a grin. “In my culture, strong, independent women pay for themselves. It’s empowering.”
As I stood up to leave, I dropped some cash for my meal on the table and said, “It was lovely meeting you both.”
Walking out into the cool night air, I couldn’t help but chuckle. That date didn’t go as planned, but I’d managed to flip the script on them. They had come to take advantage of me, but I’d turned the tables in the most satisfying way possible.
Sometimes, the best way to handle entitled people is to give them a taste of their own medicine. This was one first date I’d never forget—and a valuable lesson in standing up for myself with humor and wit.