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.
I Promised a Homeless Man I’d Find Him a Family in One Evening – But First, We Went to a Salon and a Boutique
Mark meets Stuart, a homeless man, on a busy city street and makes an unusual promise to change his life in just one evening. He starts by giving Stuart a fresh haircut and buying him new clothes, determined to find him a family by the night’s end. But can Mark truly fulfill this bold promise and transform Stuart’s life?
A homeless man | Source: Freepik
You never know who you’ll encounter in life and how they might change your world.
I’m Mark, and a few days ago, I had this wholesome experience I will never forget.
So, I was sitting on a busy city street, munching on my sandwich during lunch break.
A man holding a half-eaten sandwich | Source: Pexels
Out of nowhere, this scruffy-looking guy walks up to me and hands me my wallet.
“Hey, you dropped this,” he said.
I was stunned. “Thanks, man! I didn’t even notice. What’s your name?” I asked, genuinely curious.
A wallet | Source: Pexels
“Stuart,” he replied with a shy smile.
“I’m Mark,” I said, shaking his hand. “I’m a barber. How about I repay you with a fresh haircut?”
Stuart looked down at his worn-out clothes and shrugged. “Why bother? I got no one to impress. Nobody cares about a bum like me.”
I imagined being in Stuart’s shoes, and his words hit me right in the feels. I knew I had to do something more.
A man thinking about something | Source: Pexels
“How about this,” I said, my mind racing. “I bet you I can find you a family in one evening!”
Stuart laughed, thinking I was joking, but I grabbed his hand. “Bet on it!”
I could see he wasn’t really sure, but he agreed.
We headed straight to my shop. “Come on in, Stuart,” I said, holding the door open for him as we arrived. The place was buzzing with activity. My colleagues and a few customers gave us curious looks as we walked in.
Inside a barbershop | Source: Freepik
I pointed to the chair. “Take a seat, Stuart. Let’s see what we can do.”
Stuart hesitated for a moment but then sat down. I draped the cape over him and got to work. “You’re in for a treat,” I said, picking up my clippers.
A man cutting hair | Source: Pexels
As I started cutting his hair, I could see the change happening right before my eyes. The scruffy, tired look began to disappear. Stuart was getting a fresh start, and it showed.
“How’s it looking?” Stuart asked, a bit nervous.
A smiley man at a hair salon | Source: Freepik
“Trust me, you’re going to look great,” I replied, focusing on giving him the best cut possible. Other barbers started to gather around, watching the transformation.
“Wow, Mark, you’re doing wonders,” one of them said, impressed.
A hairdresser standing in a barber shop | Source: Freepik
When I was done, I turned the chair around so Stuart could see himself in the mirror.
His eyes widened. “Is that really me?” he asked, touching his newly styled beard and hair.
“Yep, that’s you,” I said, smiling. “What do you think?”
An elderly man looking into a mirror | Source: Freepik
Stuart grinned, looking a bit shy. “I feel like a new man. But do you think it’s too fancy for a guy like me?”
Everyone in the shop chuckled.
“Not at all,” I said. “You deserve this.”
A man laughing | Source: Pexels
Stuart’s confidence seemed to soar. He stood up a bit straighter, and there was a sparkle in his eye that hadn’t been there before. “Thanks, Mark. This feels amazing,” he said.
But it wasn’t over yet. After the haircut, I decided it was time to get Stuart some new clothes.
Outfits on display inside a boutique | Source: Pexels
We walked over to a nearby clothing boutique. As we stepped inside, the staff greeted us with friendly smiles.
“Hi there! How can we help you today?” one of them asked.
“We need to find my friend Stuart here some stylish clothes,” I said, patting Stuart on the back. Stuart looked around, a bit overwhelmed. “I’ve never been in a place like this,” he whispered to me.
“Don’t worry, we’ll find something great,” I assured him. The staff quickly got to work, bringing out various outfits for Stuart to try.
A man selecting clothes | Source: Pexels
His reactions were priceless. “These pants are so tight! How do people breathe in these?” he said, making everyone laugh.
I handed him a shirt. “Just try it on, Stuart. You’ll look great.”
He reluctantly took the clothes and went into the changing room. A few minutes later, he came out, looking unsure. “How do I look?” he asked.
A man looking at outfits curiously | Source: Freepik
“Wow, Stuart, you look fantastic!” I said, giving him a thumbs up. The staff nodded in agreement.
Stuart looked at himself in the mirror, turning this way and that. “I feel like I’m wearing someone else’s clothes,” he said with a laugh. “But they do look nice.”
An older man in a suit | Source: Midjourney
“Exactly, that’s the point,” I said. “You deserve to feel good about yourself.”
After trying on a few more outfits and making everyone laugh with his witty comments, Stuart finally settled on an outfit that made him feel comfortable yet stylish.
“I think I’ll stick with this one,” he said, smiling.
A confident elderly man in a suit | Source: Pexels
“Great choice,” I said. “You’re looking sharp, my friend.”
Stuart’s confidence seemed to grow even more. “Thanks, Mark. I really appreciate this,” he said, enveloping me in a hug.
“No problem. We’re just getting started,” I said, feeling excited about what was to come.
An elderly man hugging a young man | Source: Pexels
With Stuart looking sharp, we decided to grab dinner at a cozy café.
As we walked in, Stuart seemed nervous. “I haven’t been to a place like this in years,” he admitted.
“Relax, Stuart. It’s just dinner. Enjoy it,” I said, guiding him to a table.
Inside a cafe | Source: Unsplash
We sat down and ordered some food. While we waited, I pulled out my phone. “How about we set up a date for you?” I suggested.
“A date? You’re serious?” Stuart asked, his eyes widening.
“Why not? Let’s give it a shot,” I said, smiling.
A happy man using his phone | Source: Pexels
I registered him on a dating site and quickly set up a profile. Within minutes, we got a response from a woman named Linda. She agreed to meet us at the café.
When Linda arrived, she seemed interested at first. Stuart stood up and introduced himself, looking a bit nervous. “Hi, I’m Stuart,” he said, offering his hand.
A beautiful senior woman | Source: Freepik
Linda shook his hand, but her smile faded as we talked. When she found out Stuart was homeless, her expression changed.
“You should have been honest,” she said, standing up abruptly.
“Wait, Linda, he’s a great guy,” I tried to explain, but she was already walking out the door.
Stuart sat back down, looking dejected.
An elderly man looking sad | Source: Pexels
“I’m sorry, Stuart,” I said, feeling bad for him.
To my surprise, he smiled. “It’s alright, Mark. Today is still one of the best days of my life. It reminded me of when I used to go out with friends and meet girls.”
I didn’t know what to do at that point. I had promised him I would help him find a family, and I knew that I had failed to do so.
But the next morning, on my way to work, I saw something that made me stop in my tracks.
A man walking on a road | Source: Pexels
Stuart was sitting outside a supermarket, chatting with a woman. They were both smiling and laughing.
I walked over, curious. “Hey, Stuart!” I called out, waving.
“Mark! Good to see you,” Stuart replied, standing up and giving me a big smile. “I want you to meet Maria.”
A happy elderly couple | Source: Pexels
Maria stood up and shook my hand. “Hi, Mark. It’s nice to meet you,” she said warmly.
“Nice to meet you too, Maria,” I said, looking at Stuart with a raised eyebrow. “Where did you two meet?”
“Believe it or not, we met last night after the date fiasco,” Stuart said with a chuckle. “Maria was kind enough to sit and talk with me. We’ve been chatting ever since.”
Maria smiled at Stuart. “Stuart told me everything. I’ve had my own struggles, so I understand where he’s coming from.”
A couple holding hands | Source: Pexels
I felt a surge of happiness and pride. “That’s wonderful to hear,” I said, genuinely moved. “You two seem to get along really well.”
“We do,” Stuart said, looking at Maria with a grateful smile. “Thanks to you, Mark. That bet led to something really good.”
“I’m just glad to see you happy, Stuart. You deserve this,” I said, and we shared a hug.
A happy man | Source: Pexels
I still can’t believe it all happened.
Life has a funny way of surprising us, doesn’t it? Stuart found a friend, and maybe even a family, through a series of events that started with a lost wallet. And I learned that sometimes, all it takes is a little compassion to change someone’s life.
Have you ever witnessed something like this or changed someone’s life for the better?
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