Who brings their parents to a first date? My boyfriend from a dating app did. But what really got me was the list of OUTRAGEOUS DEMANDS his parents brought with them. I knew I’d have to outwit them… but on my own terms.
When I virtually met Jacob on a dating site several months ago, we hit it off instantly. The connection felt real — the kind that makes your heart skip a beat when you see a new message notification. I grew to think that he was “the one,” but then when we actually met… well, let’s just say reality has a way of shattering our perfectly crafted illusions.
A woman holding a phone | Source: Unsplash
Three months of late-night texts and hour-long video calls had built up to this moment. Jacob wasn’t just another match; he was different.
While most guys led with cheesy pickup lines or bland “hey” messages, he had caught my attention with a detailed comment about my profile photo taken at Comic-Con.
“Is that a handmade Scarlet Witch costume?” he’d written. “The detail work is incredible!”
From there, our conversations flowed naturally. He listened, really listened, when I talked about my work as a graphic designer and my dreams of starting my own studio.
A woman using a computer | Source: Midjourney
He shared my love for true crime podcasts and could quote every episode of my favorite shows by heart. When I mentioned my sister’s battle with depression, he opened up about his own experiences with anxiety.
“I feel like I can tell you anything,” he’d said during one of our video calls, his warm brown eyes crinkling at the corners. “I’ve never connected with someone like this before.”
“Me neither,” I’d admitted, feeling my cheeks flush. “Sometimes I worry this is too good to be true.”
He’d laughed then, running a hand through his dark hair. “I can’t wait to finally meet you in person. Friday at Coffee Beanz? 7 p.m.?”
A man using a laptop | Source: Pexels
“It’s a date! Finally!” I’d chirped, unable to contain my excitement.
“See you on Friday!” He said as I hung up, blushing.
I spent the entire week planning my outfit, finally settling on a gorgeous dress that my best friend Sarah insisted brought out my eyes.
“He won’t know what hit him,” she’d said, helping me style my hair.
Friday evening found me standing outside Coffee Beanz, smoothing down my dress for the hundredth time. Through the window, I could see couples enjoying their meals, soft candlelight flickering across their faces.
People in a cafe | Source: Unsplash
My hands were shaking slightly as I pushed open the heavy wooden door, the warm aroma of garlic and fresh bread enveloping me. My eyes nervously darted around in search of Jacob.
“Lia! Over here!”
I turned toward Jacob’s familiar voice, my practiced smile freezing on my face. There he sat, but not ALONE.
An older couple sat beside him, their faces beaming with smiles. My heart, which had been filled with excitement all day, sank to my stomach.
“Hey… um, hi, what’s going on?” I managed, my brain struggling to process the scene before me.
A shocked woman | Source: Pexels
Jacob stood up, his bright smile unchanged as if this was completely normal. “Lia, I’m so excited to finally meet you! These are my parents, Linda and Patrick!”
Linda, a petite woman with perfectly coiffed gray hair and gold earrings that probably cost more than my monthly rent, gave me a practiced smile that didn’t reach her eyes. Patrick, sporting a dress shirt that seemed a size too small for his frame, barely looked up from his menu.
“Sit down, girl,” Linda patted the chair next to her, not next to Jacob. “While we wait for our appetizers, I have a few questions for you.”
An older lady smiling | Source: Midjourney
I sank into the chair, still trying to make sense of this ambush. The waiter appeared with water glasses, and I found myself wishing it was something stronger.
That’s when Linda pulled out a crisp sheet of paper from her designer handbag.
“Now then,” she cleared her throat, clicking her gold-plated pen. “I’ve prepared a brief questionnaire to help us get to know you better. I want you to fill it out.”
Sheets of paper on a table | Source: Pexels
My eyes scanned the paper she placed before me, each question worse than the last:
1. What is your current annual income and five-year career projection?
2. Please list any medical conditions, including a family history of genetic disorders.
3. How many romantic partners have you had, and what were the reasons for those relationships ending?
4. Do you own or lease your vehicle? What is your credit score?
5. Are you willing to sign a prenuptial agreement?
6. Do you plan to work after having children? If so, who will provide childcare?
7. What is your stance on living with in-laws?
8. Are you willing to host special occasions like Thanksgiving & Christmas every year without expecting a penny from your partner?
A startled woman covering her mouth | Source: Pexels
The questions went on and on like a never-ending train carriage. My water glass stopped halfway to my mouth. “I’m sorry, but is this for real?”
“Of course it is, dear,” Linda replied, her tone suggesting I was being deliberately difficult. “Our family has certain standards to maintain. We need to ensure any potential partners for our Jacob are… suitable.”
My eyes darted to Jacob, waiting for him to jump in, to say this was all a joke. But he just sat there, examining his napkin as if it held the secrets of the universe.
A man sitting casually | Source: Midjourney
Something snapped inside me. Three months of building this connection, sharing hopes and fears, only to be treated like a job applicant? No. This called for a different approach.
“Would you excuse me for just a moment?” I smiled sweetly. “Ladies’ room.”
Instead of heading to the restroom, I ducked into the convenience store next door. Five minutes later, I returned with my own notebook and pen.
“Before I answer your questions,” I said, sitting down with renewed confidence, “I have a few of my own.”
A woman holding a piece of paper | Source: Pexels
Linda’s perfectly plucked eyebrows shot up in surprise as I placed the paper with my questions on the table. She picked it up and began reading loudly, her face speaking volumes of her anger.
“Question one: At what point did you realize your son wasn’t capable of choosing his own partner?”
Patricks’s face reddened. Jacob finally looked up from his napkin.
“Question two: How many women have actually completed your interrogation process? Or do most run screaming before the credit check?”
“This is completely inappropriate!” Linda’s voice pitched higher as she continued to read.
A furious older woman with a man | Source: Midjourney
“Question three: Do you also inspect their teeth like show horses, or is that saved for the second date?”
“Question four: When Jacob moves out of your basement, will you be requiring his future wife to submit weekly progress reports?”
“Question five: Have you considered therapy for your control issues, or is that too personal a question?”
“That’s enough!” Jacob slammed his hand on the table, making the silverware jump. “You have no right to disrespect my family like this!”
An angry man | Source: Midjourney
I leaned back, crossing my arms. “Oh, but they have every right to treat me like I’m applying for a position at the FBI?”
“My parents are just looking out for me,” he protested, his voice weak. “They want what’s best— “
“No, Jacob. What’s best for you would be growing a backbone and living your own life.”
Linda and Patrick were already gathering their things, faces flushed with indignation. Linda’s hands shook as she stuffed her questionnaire back into her bag.
“We’re leaving,” she announced. “Jacob, come on. She’s not the one for you.”
“Wait!” I called out, loud enough for nearby tables to turn. “Aren’t you forgetting something?”
Side shot of a woman | Source: Midjourney
They paused. “WHAT??”
“Waiter, these people are trying to leave without paying their bill!” I announced loudly, waving to the waiter. “Guess running out on checks is another proud family tradition!”
The restaurant had gone quiet. Linda’s hands shook as she pulled out her credit card, practically throwing it at the waiter. I stood up, smoothing my dress once again.
“Well, this has been entertaining. I’ll cover my water.” I placed a five-dollar bill on the table and turned to Jacob.
“Good luck finding someone who meets your family’s rigorous standards. Although, you might want to try job recruitment sites instead of dating apps. I hear they provide detailed background checks and references.”
A woman laughing | Source: Midjourney
As I walked out into the cool evening air, my phone buzzed with a message from Jacob, “You didn’t have to be so cruel. My parents were just looking out for me.”
I typed back, “Just looking out for myself, mama’s boy. Goodbye!”
Later that night, Sarah called to hear about the date. After I finished telling her everything, she was quiet for a moment.
“You know what?” she finally said. “I bet Linda has a spreadsheet ranking all of Jacob’s potential wives.”
We both burst out laughing, and I felt the last of my disappointment melt away. Dodged a bullet? Absolutely. And I’ve never been so grateful for a red flag wrapped in a questionnaire.
A woman walking away | Source: Midjourney
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.
Matt Heath: My parting message: Enjoy things while they are around
A lot of big, tragic and important things have happened to this wonderful country of ours since April 2014. None of which I have covered. I was too busy writing about hungover parenting, ancient philosophy and my dog Colin.
Out of the 536 columns I have written, 27 were about that guy. Far too few. He is such a good boy, he deserves an article a week.
Today is the end of an era for me, and whenever these final events pop up in our lives, we can’t help but think about the ultimate end.
Everything we do, we will one day do for the last time. That’s why you have to enjoy things while they are around. It’s not just big events like leaving a job, house or loved one either. Whatever moment you happen to be in now, you will never get it back, and you don’t know how many more you have.
Everything we do in life, from eating pizza to spending time with the people we love, to driving, writing, drinking or breathing, we will one day experience for the final time. It might happen tomorrow. This can be either a depressing or an inspiring thought, depending on how you look at it.
A few years back in this column, I interviewed professor of philosophy William B Irvine, of Wright State University, Ohio, on this very topic. He put it this way on a Zoom call: “Recognition of the impermanence of everything in life can invest the things we do with a significance and intensity that would otherwise be absent. The only way we can be truly alive is if we make it our business periodically to entertain thoughts of the end.”
Today’s column is very meaningful to me because it is my last. Like the last night with a lover before she goes overseas. And just like a lover, there have been some half-arsed efforts put in from me over the years. Last week, for example, I spent 750 words moaning about how bad my cricket team is. But the truth is that any of my columns could have been the final. If I had reminded myself every week for the past 10 years that the end is inevitable, I may have been more grateful for having a column and appreciated writing them all as much as I am this one.
While everything we do could have more meaning with a focus on finitude, some things are inherently more worthwhile than others. There is no doubt my column “The pros and cons of wearing Speedos” from November 2022 was less meaningful than most things in this world. That was a waste of everyone’s time. So, if we only have so much time, how do we pick the best things to do?
Well, Oliver Burkeman, the author of Four Thousand Weeks – Time Management For Mortals, suggested this to me in a 2022 column: “Ask yourself, does this choice enlarge me? You usually know on some unspoken level if it does. That’s a good way to distinguish between options.”
With that in mind, I don’t feel great about my 2018 article on “New Zealand’s best hole”. That didn’t enlarge anyone.
There will be people reading this column right now who have loved my writing in the Herald and are sad to see it end. Others will have hated it and are glad to see me go. Many won’t have any opinion at all. But for those in the first camp, I have good news. I have a book coming out on May 28 called A Life Less Punishing – 13 Ways To Love The Life You Got (Allen and Unwin Book Publishers). It’s a deep dive into the history, philosophy and science of not wasting our time lost in anger, loneliness, humiliation, stress, fear, boredom and all the other ways we find to not enjoy perfectly good lives. It’s available for pre-order right now (google it if you’re interested).
A Life Less Punishing took me two years to write and is equivalent in words to 100 of these columns. Which would be a complete nightmare for those in the hate camp, but as I say, great news for those who want more.
Anyway, thanks to the Herald for having me, thanks to the lovely people who make an effort to say nice things to me about my column nearly every day and thanks to the universe for every single second we get.
Bless!
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