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 Bought Food for a Homeless Man, He Stunned Me with His Confession the Next Day
I bought a warm meal for a homeless man, thinking it was just a small gesture of kindness. But when he found me the next day with his eyes full of tears and a confession that broke my heart, I realized how powerful even the smallest acts of compassion can be.
They say a little act of kindness goes a long way. But when I decided to help a hungry homeless man one day, I wasn’t prepared for the heart-wrenching encounter that followed less than 24 hours later. This stranger I helped with food made a confession that brought me to tears and reminded me why some people cross our paths when we least expect it.
A sad homeless man asking for help | Source: Pexels
Between the past two days, my life turned into something straight out of an inspirational movie.
I’m a mom of four wonderful, chaotic children ranging from four to eight years old. Life is a constant juggling act between my part-time teaching job and managing our home while my husband Mason works as an engineer.
Our life isn’t fancy, but the laughter of our kids fills every corner of our modest house with joy.
A woman with her children | Source: Pexels
That morning started like any other. I had my wrinkled shopping list in one hand and my desperately needed coffee in the other, mentally calculating how to stretch our budget through another week of feeding four growing children.
The fluorescent lights of Happinezz Mart buzzed overhead as I stood in the parking lot, gathering my energy for the weekly shopping marathon. The morning air was crisp, carrying the first hints of winter as I pulled my cardigan tighter around myself.
That’s when I saw him. A homeless man, holding a desperate sign that read, “HELP.”
The first thing I noticed was his eyes. They weren’t looking at me, or anyone else… just fixed on the displays of fresh bread and fruit through the grocery store window.
A homeless man on the street | Source: Pexels
His weathered jacket hung loose on his thin frame, and his gray hair poked out from under a worn cap. His hands, I noticed, were clean but rough, like someone who had worked hard his whole life.
I don’t know what made me stop. Maybe it was the way his shoulders slumped, or how his fingers unconsciously moved toward his empty stomach.
Maybe it was because he reminded me of my father who’d passed away last year with that same quiet dignity in the face of hardship.
Dad had always taught us that true strength wasn’t in never needing help, but in being brave enough to accept it when offered.
An emotional woman looking at someone | Source: Midjourney
“Excuse me, sir,” I approached the man. “Are you hungry? Would you like something to eat?”
He turned to me slowly and I saw desperate hunger in his eyes.
“More than you can imagine, young lady! I haven’t eaten since yesterday morning.”
My heart broke for this man. How often do we walk past the homeless, oblivious to their suffering? And how often do we see beyond their situation and offer them compassion, not just a piece of bread?
A hungry homeless man | Source: Pexels
“Please, come shop with me, sir. I’m Greta. I’ll pay for your groceries.”
“Miss, I can’t accept—” he hesitated, but I cut him off gently.
“I insist. Besides, I could use some company while I shop. My kids aren’t here to argue about which cereal has the better toy inside. And honestly, shopping alone is pretty boring.”
A small smile cracked through his weathered face. “I’m Morgan. And… thank you. You remind me of my late daughter, Grace. She always helped people too.”
A supermarket | Source: Pexels
Walking through the aisles with Morgan was an exercise in humility. He’d reach for the cheapest bread, the marked-down cans, pulling his hand back whenever he thought he was asking for too much.
Each time he apologized, my heart would break a little more.
“These are good,” he said softly, pointing to some discount soup cans. “They last a while. And they’re easy to heat up if… well, if you can find a place to heat them.”
Soup cans stacked on a supermarket shelf | Source: Unsplash
“Let’s get some meatloaf and mashed potatoes, too,” I suggested, steering us toward the deli section. “When’s the last time you had a proper, hot meal?”
Morgan’s eyes misted over. “Been a while. Used to grow my own vegetables and sell them to buy those delicious meals, you know. Had a little garden behind my house. Tomatoes, cucumbers, even some strawberries.”
As we walked, I found myself talking about my family, filling the awkward silence with stories about my kids. Morgan listened intently as if each word was precious.
A sad older man | Source: Pexels
“My kids would love these,” I said, tossing some cookies into the cart. “The twins, they’re six, and they’d eat the whole package if I let them. Last week, they tried to convince me that cookies counted as breakfast!”
Morgan’s eyes softened. “How many children do you have?”
“Four of them,” I laughed, pulling out my phone to show him a picture. “The twins, Jack and James, they’re convinced they’re going to be soccer stars, even though they trip over their feet half the time. Then there’s little Lily, she’s four and obsessed with bubble gum. She once stuck gum in her brother’s hair and we had to cut it out. And Nina, my eight-year-old bookworm.”
A woman smiling | Source: Midjourney
“She looks just like you,” Morgan said, pointing to Nina in the photo. “Same smile, same kind eyes. You have such a beautiful family.”
“That’s what my husband always says. Though I think she got his brains, thank goodness! She’s reading at a sixth-grade level already. Sometimes I find her up past bedtime, flashlight under the covers, cooing, ‘Just one more chapter, Mom, please?’”
“They’re beautiful. You must be very proud. Sometimes I wonder…” Morgan trailed off, and I pretended not to notice as he wiped his eyes with his sleeve.
A distressed older man | Source: Pexels
As we checked out, I noticed his hands trembling slightly as he helped bag the groceries.
When I handed him his bags, including both gallons of milk I’d bought, his eyes welled up.
“I don’t deserve this kindness.”
“Everyone deserves kindness, Morgan. Everyone.”
“Thank you, ma’am! God bless you.”
And with that, we parted ways as I watched Morgan sit on the parking lot’s steps, happily eating his meal.
A homeless man eating his meal | Source: Pexels
The next morning, my kids frustratingly stared at their dry cereal bowls. Jack pushed his bowl away dramatically, while James pointed out that this was clearly the end of the world.
“Mom,” Nina looked up at me, “did you forget to buy milk yesterday?”
“Oops, sorry, honey! I’ll get it today, okay?”
I’d forgotten that I’d given both milk gallons to Morgan, so here I was, back at the same grocery store, ready to face the morning rush. The twins had gone to school with promises of chocolate milk in their lunch boxes tomorrow to make up for the breakfast disaster.
A woman in a grocery store | Source: Pexels
The parking lot was busier, filled with moms like me doing their morning shopping. A school bus rumbled past, reminding me I had only an hour before I needed to be at school myself, ready to face a classroom of energetic third graders.
The sound of car doors slamming and shopping carts rattling filled the air.
I almost walked past him. The straight-backed man in the crisp military uniform couldn’t possibly be the same person I’d helped yesterday. But those eyes… I recognized them immediately.
A man in a military uniform | Source: Midjourney
“Greta,” he called out, his voice stronger than yesterday. “I hoped you’d come back. I’ve been waiting since dawn.”
“Wait a minute… aren’t you the homeless man I helped yesterday? Morgan, right?”
He gestured to a nearby bench. “Would you sit with me for a moment? I owe you an explanation. And maybe a thank you isn’t enough, but it’s where I need to start.”
A stunned woman | Source: Pexels
“I was a Master Sergeant,” Morgan began, his fingers running over his uniform’s sleeve as we sat on the bench. “Twenty-six years of service. Lost good friends. Young men who never got to come home. But coming home… it was harder than leaving ever was.”
“What happened?” I asked softly, noticing how his hands clenched and unclenched as he spoke.
“PTSD. Depression. The usual story. My wife passed while I was overseas. Cancer. A year earlier, I’d lost my daughter in a tragic accident. Coming back to an empty house…” he shook his head.
A sad man with his eyes downcast | Source: Midjourney
“The silence was the worst part. No one telling me to take my boots off before coming inside. No one breathing beside me at night. No one to call me… Dad. One day, I just walked away from everything. Couldn’t handle the memories. I thought it was the only way to escape the pain.”
I reached out and squeezed his hand, my eyes moist. He squeezed back, his grip firm but gentle.
“Yesterday, when you looked at me — really looked at me — and showed me such simple kindness… it broke something loose inside.” Morgan’s voice wavered.
An emotional woman | Source: Unsplash
“And after you left, I stood there holding those bags of groceries, and for the first time in years, I felt human again. Not just a shadow sliding past people on the street.”
“So I walked into the VA office. Just walked right in. The lady at the front desk, she…” he paused, collecting himself. “She hugged me. Said they’d been worried sick about me. Turns out my old commanding officer had been looking for me for months. He even had people out searching the streets. I just… I never thought anyone would care enough to look.”
A man smiling | Source: Midjourney
“They’re giving me a chance to help other vets,” Morgan continued, his face lighting up. “There’s this new program for soldiers just coming home. They want me to be a mentor and help them re-adjust before the darkness sets in. Share my story, you know? Show them there’s hope, even when it feels like there isn’t.”
“Morgan, that’s wonderful!” I felt tears sliding down my cheeks.
“Your kindness… it reminded me that I still have something to give,” he said, straightening his uniform jacket. “This morning, I got my first shower in months. Got my old uniform out of storage. Feels strange to wear it again. But positively strange. Like coming home… to a home I’m ready for this time.”
A sad woman | Source: Midjourney
He reached into his pocket and pulled out two gallons of milk. “These are for your kids. Bought them just now. Can’t have your little ones missing their breakfast because of me. And this—” he pressed a folded piece of paper into my hand, “is my number. If you ever need anything, anything at all…”
“What about you? Will you be okay?” I asked, still worried.
“The VA’s got me set up in temporary housing. Starting counseling tomorrow. And next week, I start working with the new vets. Turns out my experience… even the bad parts… they might help someone else make it through.”
Portrait of a cheerful man smiling | Source: Midjourney
I hugged him tightly, not caring who saw. “Promise you’ll keep in touch?”
Morgan smiled, and this time it reached his eyes.
“Promise. Just keep teaching those kids of yours about kindness, Greta. It saves lives. I’m living proof of that. And maybe someday I can meet them. Tell them some stories about their mom, the angel who saved an old soldier’s life with food and a gentle word of kindness.”
A man looking at someone with a warm smile | Source: Midjourney
I watched him walk away, his uniform gleaming in the morning sun, his steps sure and purposeful. My heart feels so full knowing Morgan is safe and cared for now. That he’ll have a warm bed, regular meals, and most importantly, a purpose again.
Sometimes the smallest acts of kindness create the biggest ripples, and I’m just grateful I got to be a part of Morgan’s story.
A smiling woman looking at someone | 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.
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